1. Editorial Policy of Arkivoc
1.1 Manuscript requirements
It is the responsibility of the senior author to ensure that all named authors have made a significant contribution to the work described in the manuscript and that all authors have seen and approved
the manuscript prior to submission.
The manuscript of a full paper must be based on original research
by the authors and the work must not have been published previously either in print or electronic format (exception: dissertations).
Manuscripts should be submitted to Arkivoc on an exclusive basis and must not be under simultaneous consideration by another journal.
If reference is made to an unpublished paper (“submitted” or “in press”), a copy of that manuscript should be provided by the author with the submission.
Arkivoc is an organic chemistry journal and does not publish papers that are primarily concerned with medicinal chemistry. The journal does publish manuscripts with some medicinal chemistry content if the synthetic chemistry is novel and of general interest to organic chemists. Biological test results, if included, should form only a minor part of the manuscript, and biological results that are particularly significant or promising are more suitable for a medicinal chemistry journal. The final decision to publish such papers resides with the editors.
1.2 Evaluation of manuscripts
Contributions will be evaluated initially by the Primary Review Committee. Manuscripts that fulfil the essential scientific and editorial requirements for publication in Arkivoc will be reviewed by two or more members of the Editorial Board of Referees who advise the Scientific Editors on the suitability for publication. Authors are requested to submit three suggestions for referees
Manuscripts that are unsound or have inadequate characterization of new compounds will not be accepted.
1.3 Date of receipt
The "date of receipt" recorded in the published article will be the date when a complete submission that satisfies all the requirements of the Technical Editor is received in the editorial office.
2. Preparation of Manuscript, Supplementary Materials, and Graphical Abstract
(Please note that "Communications" are not published in Arkivoc)
2.1 Manuscript text
Because Arkivoc is published online and in a printed version, it is essential that the files for both versions are compatible. In order to achieve this, authors are required to use the appropriate template for the preparation of a paper
, or review
. If, for technical reasons, this is not possible, the following format must be strictly adhered to. Failure to comply will result in the paper being returned for amendments before further consideration. Authors should refer to the sample paper or review for precise details of layout and format. For guidance on grammar, and chemical-usage in the preparation of manuscripts authors are recommended to consult The ACS Style Guide
, Coghill, A. M.; Garson, L. R. Eds.; 3rd Edn.; Oxford University Press, 2006 (ISBN-13; 978-0-8412-3999-9). In a case of conflict between these sources, follow usage in a recent
Arkivoc paper on the website.
2.1.1 The language of publication
2.1.2 Word processor
Manuscripts must be prepared using MS Word as a doc file.
Manuscripts in pdf format CANNOT be accepted.
2.1.3 Macros and bookmarks:
manuscripts containing macros and bookmarks CANNOT be accepted.
2.1.4 Text file format
page size: US Letter (8.5 by 11 in, 22 by 28 cm.); margins on all sides are 1 in (2.54 cm).
setting "at least 16 pt."
Times New Roman.
12 pt, normal, justified (left and right).
Special characters (Greek letters, accents, mathematical symbols) must belong to the Times New Roman character set, i.e. must belong to the "normal text" Font in the Symbol selection window.
2.2 Organization of the manuscripts
2.2.1 Manuscripts for original research papers should have the following headings:
The title should clearly describe the purpose of the paper and should not include abbreviations (16 pt, bold, centered; followed by one empty line). Only the first letter of the title and of proper names in the title (e.g., Lewis acid) should be capitalized.
2.2.4 Author's name(s)
Typically, the following should be provided for each author:
Given name, middle initial and surname (12 pt, bold, centered; followed by one empty line).
The name of the corresponding author should be marked with an asterisk (*). If authors are from different institutions their surnames should be labeled after the name with a lower case superscript letter referring to the authors' addresses.
Example: Albert J. Jones,a Dalpat Patel,b and Arthur Otherb*
The senior author must have the agreement of all authors for their names to appear on the paper.
2.2.5 Author's address(es), corresponding author's e-mail address
The complete mailing address(es) of author(s) should include the name of the institutional affiliation, street or P.O. box number, city, postal code, and country (12 pt, italic, centered).
The address line should be followed by the e-mail address of the corresponding author (12 pt, italic, centered; with hyperlink; followed by one empty line).
If a Dedication
is desired, it should appear after a one line space below the e-mail address (12 pt, bold, centered).
All manuscripts must be accompanied by a written abstract, which should state the purpose of the research, the principal results and major conclusions. The use of numbers in the abstract identifying formulas or tables is discouraged because the abstract text should be comprehensible when read alone. A typical abstract should contain no more than 100 words.
Heading: 12 pt, bold, justified. Abstract text (on next line): 12 pt, normal, justified; followed by one empty line.
the Abstract should be followed four to six keywords.
12 pt, bold, colon, followed by keywords (first one capitalized and separated by commas): 12 pt, Times New Roman, left justified. There should be two spaces before the next heading.
2.2.9 Headings font size and style, alignment:
Major section headings
(Introduction, Results and Discussion, Experimental Section, References, etc.): 14 pt, bold, left justified. There should be two spaces between sections and one space between each section heading and the text. The first paragraph of the text after major headings should not be indented.
12 pt, bold, left justified. Text begins on the following line and should not be indented.
should be indented (recommended 0.25 in or 0.64 cm) except the first paragraph after a section heading. In the Experimental Section paragraphs should not be indented.
2.2.10 Reviews and Accounts - Table of Contents (ToC)
A ToC should appear above the Introduction for Reviews and Accounts. Headings in Reviews and Accounts should follow the hierarchy and style as indicated below. The Introduction should be numbered 1.
1. Primary Heading (12pt)
1.1 Secondary heading (12pt)
1.1.1 Tertiary heading. (12pt, run on)
2. Primary Heading
An introductory paragraph or statement should be given, placing the work in the appropriate context and clearly stating the purpose and objectives of the research.
2.2.12 Results and Discussion
All significant results that need to be rationalized should be discussed in this section. Experimental details should be kept to a minimum and reiteration of information from Tables, Figures, and Schemes should be avoided.
A brief Conclusions section is desirable, but not essential.
2.2.14 Experimental Section
This section should contain a description of instruments (make and model), and any special procedures used. The sources of all commercially available chemicals along with the source of all combustion analytical data, or work done outside the authors’ institution should be given.
in the experimental section should be accompanied by a listing of the most important product characterization data. Each paragraph describing a synthetic experiment should give the product’s systematic (IUPAC) name and the structure number assigned to the compound in the discussion section. Use of standard abbreviations or unambiguous molecular formulas for reagents and solvents, and of structure numbers rather than chemical names to identify starting materials and intermediates, is encouraged. Reactant and reagent quantities should be given in both weight and molar units. Yields should represent weighed amounts of isolated and purified products, and should be reported as percentages. When flash chromatography is used for product purification, both the support and eluting solvent should be identified.
Abbreviations, acronyms, symbols, and physical constants.
Common abbreviations, acronyms, and symbols may be used, but less common ones should be defined the first time they are used (see the ACS Style Guide). Usage within a paper should be consistent, e.g., either Ph or C6
for phenyl, not both. Note: Ph should not be used for C6
. The symbols used for physical constants should be in italics (e.g. d, J, k, c, m/z
), but the units for physical constants should not
be italicized. Equal signs should be avoided in citing data, e.g. J
5.1 Hz not J
= 5.1 Hz.
Arkivoc considers only those QSAR papers that meet the following criteria: (i) the work must involve statistical treatment of results obtained from the authors’ laboratory (they must not be culled from the published literature) and (ii) the paper should include a practical (experimental) element, as appropriate to an organic chemistry journal.
Work conducted in microwave reactors must indicate whether sealed or open reaction vessels were used and must document the manufacturer and model of the reactor, the method of monitoring the reaction mixture temperature (external surface sensor or internal probe), and the temperature reached or maintained in each experiment. Please note that Arkivoc does not publish reports of studies conducted with domestic (kitchen) microwave ovens
Compound characterization data.
Arkivoc upholds high standards for compound characterization to ensure that compounds being added to the chemical literature have been correctly identified and could be synthesized in known yield and purity by the reported preparation, isolation, and purification methods. For all new
compounds, evidence adequate to establish both identity
and degree of purity
(homogeneity) must be provided. Purity documentation must be provided for known
compounds whose preparation by a new or improved method is reported. If, in the opinion of the Scientific Editor, new compounds have not been satisfactorily characterized, the paper will not be accepted
For known compounds synthesized by published methods, the method of preparation, the literature data used to confirm the identity of the material, and the technique(s) used to determine purity should be reported. For known compounds prepared by new or modified synthetic reactions, the types of physical and spectroscopic data that were found to match cited
literature data should be identified, and purity documentation (see below) should be provided. Listings of IR and NMR absorptions and MS peaks for known compounds should be included only if they do not duplicate published data.
Evidence for the identity of new compounds should include both 1
H and 13
C NMR data and
either HRMS or elemental analysis data. A criterion of purity (see below) must also be provided with HRMS data.
Proton and carbon NMR
resonance signals should be listed for each new compound; the solvent and instrument frequency should be identified. Carbon NMR peak shifts should be rounded off to the nearest 0.1 ppm. Hydrogen multiplicity (C, CH, CH2
) information (APT) obtained from carbon DEPT or 2D spectra may be included with the carbon peak shifts, if available, but is not essential information. The J
values for all signals described as ‘d’, ‘t’, etc., must be given. For an example of the format for reporting NMR data, see the model Experimental Section at the end of the Instructions to Authors.
For new compounds, either HRMS (resolution 0.001 m/z
unit or better) or combustion elemental analysis data should be reported to support the molecular formula assignment. The reported data should include the molecular formulae on which the theoretical (Calcd) values are based.
HRMS molecular formulae
and Calcd values should include any added atoms (usually H or Na). The ionization method should be reported and a criterion of purity provided. A Found value within 0.003 m/z
unit of the Calcd value of a parent-derived ion (for molecular weights less than 500), together with other available data (including knowledge of the elements present in reactants and reagents) is usually adequate for uniquely determining a molecular formula.
Found values for carbon, hydrogen, and nitrogen (if present) should be within 0.4% of the Calcd values for the proposed formula. The inclusion of fractional molecules of solvent or water in the molecular formula to improve the fit of the data usually reflects incomplete purification of the sample. If the reported formula includes such a molecule, independent evidence for its presence (such as NMR peaks with appropriate chemical shifts) should be presented. The format for reporting CHN analyses can be found in the model Experimental Section at the end of the Instructions to Authors.
Specific optical rotations should be reported for isolated natural products, enantiopure compounds, and enantioenriched isomer mixtures when sufficient sample is available. Specific rotations based on the equation [α] = (100.α)/(l.c
) should be reported as unitless numbers as in the following example: [α]D20
), where the concentration c
is in g/l00 mL and the path length l
is in decimeters. The units of the specific rotation, (deg.mL)/(g.dm), are implicit and should not be included with the reported value.
A melting point range
should be reported for every crystalline solid product, together with the solvent from which it was recrystallised, and a description of the material e.g. "yellow needles, mp 123-124 °C (from EtOH)". For non-crystalline materials, there should also be a description, e.g. "brown oil; colorless gum". Similarly for liquids, e.g. "colorless oil, bp 123 °C (120 mmHg)".
IR and MS.
Only those IR absorptions diagnostic for major functional groups, and only those MS peaks used for structure assignment, should be included in the experimental section. Complete peak listings or copies of the spectra may be included in the supporting information. IR bands, when reported, should be indicated using an approximate scale of relative intensities (vs, s, m, w = very strong, strong, medium, weak). Significant MS peaks should be reported with their % intensity relative to the base peak of the spectrum.
If a Scientific Editor feels it necessary to ask for evidence for compound purity, that evidence should include one or more
of the following:
1. A standard 1D proton NMR spectrum or proton-decoupled 13
C NMR spectrum showing, at most, trace peaks not attributable to the assigned structure.
2. Combustion elemental analytical values for carbon and hydrogen (and nitrogen, if present) agreeing with calculated values within 0.4%.
3. Quantitative gas chromatographic analytical data for distilled or vacuum-transferred samples, or quantitative HPLC analytical data for materials isolated by column chromatography or separation from a solid support.
4. For known solid compounds, a narrow melting point range that is in close agreement with a cited literature value.
Reproductions of spectra will be published in the results and discussion section only
when concise numerical summaries are inadequate for the discussion. Papers dealing primarily with interpretation of spectra, and those in which band shape or fine structure needs to be illustrated, may qualify for this exception. When presentation of spectra is essential, only the pertinent sections, should be included, either in the text or in supplementary information.
Only data and graphics vital to the discussion should be included in the manuscript. If the data are used solely for confirming compound identity or stereochemistry, a statement in the results and discussion or experimental section that the assignment is supported by an X-ray crystallographic structure determination is usually sufficient, though a ball-and-stick drawing or thermal ellipsoid plot can be included if desired. Regardless of the level of detail of the discussion of the structure, a Crystallographic Information File (CIF) containing complete details of data collection, crystal and unit-cell parameters, structure solution and refinement, and tables of atomic coordinates and thermal parameters, bond lengths, bond angles, and torsion angles should be furnished as supporting information. Reflection intensity data (structure factor tables) should not be included. If more than one crystal structure is being reported, the CIF for each structure should be furnished as a separate file. CIFs should be saved in text-only (plain ASCII) format and should be assigned file names that identify the structure number used in the manuscript and that include a ".cif" (not ".txt") extension. Before being submitted, CIFs should be checked and corrected using the free checkCIF data-validation utility at http://journals.iucr.org/services/cif/checkcif.html All structures for which an X-ray determination is included must also be submitted to the Cambridge Crystallographic Data Base and the unique number assigned to the compound in the data base, must be quoted in the experimental description of the compound.
For combinatorial libraries
of more than 20 compounds characterization data must be provided for at least 20 diverse members.
including, for example, molecular modeling coordinates, modeling programs, instrument and circuit diagrams, graphical kinetic data, and non-essential spectroscopic (e.g. IR, NMR, MS and UV/visible) data or other instrumental (e.g. electrochemical or chromatographic) details should be submitted in a separate Supplementary Material File (see 2.5).
2.2.16 References (and Notes)
The number of references cited should be limited to 50 for research papers. Long reference
lists should be avoided by selecting references carefully and citing reviews, or selecting recent
papers which contain many pertinent citations, whenever possible. References may appear in
the reference list followed by "and references cited therein" if appropriate. There is no limit
to the number of references that may be cited in reviews and accounts. All references must be
cited in the text in numerical order using superscripts
(without brackets). No links between
superscripts in the text
and actual references in the Reference Section
may be used.
are asked to assign a separate number to each reference cited (e.g. 1-5), groups of references may
not be nested under one number (e.g. 1a-e). All references should be listed in the "References"
section at the end of the paper in numerical order with no text between the reference number
and the first author's surname (e.g. "3. Jones, A..." not "3. See also Jones, A..."). There must
be one blank line between each reference listed.
Brief notes may be used to cite manuscripts in
preparation, unpublished observations and personal communications, but longer notes should
appear in the Supplementary Material section. Reference to experimental procedures or data
must not be included in the reference list. The Chem. Abstr.
reference should be cited for less
accessible literature (e.g., patents). Digital Object Identifier (DOI) numbers should be given for
papers cited that have been published online but have yet to receive page numbers. Authors are
responsible for obtaining written approval for all personal communications and sending a copy
of the manuscript to those cited as authors of personal communications.
References cited should follow the style below:
1. Bakke, J. M.; Gautun, H. S. H.; Sletvold, I. Arkivoc 2001
2. Herz, W.; Iyer, V. S.; Gopal Nair, M. J. Org. Chem. 1975
3. Wanner, M. J.; Koomen, G.-J. J. Chem. Soc., Perkin Trans. 1 2001
Although not essential, authors are encouraged to give both the first and last pages of papers (as
shown below) but if this is done it must be done for all the references in the manuscript.
Wanner, M. J.; Koomen, G.-J. J. Chem. Soc., Perkin Trans. 1 2001
1. Henderson, B.; McIndoe, J. S. In Comprehensive Coordination Chemistry
; McCleverty, J. A.;
Meyer, T. J. Eds.; Elsevier: Oxford, 2003; Vol. 1, p 387.
2. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry
; VCH: Weinheim, 1990; Vol.
4, pp 298-311.
3. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical
, 5th Edn.; Wiley: New York, 1989; pp 64-67.
1. Lund, K. P. Ph.D. Thesis, Univ. California, San Diego, 1992.
1. Wright, J. B. U.S. Patent 3 115 496, 1963; Chem. Abstr. 1964
, P 5512b.
2. Baylis, A. B.; Hillman, M. E. D. Ger. Offen. 2 155 113, 1972; Chem. Abstr. 1972
3. Buntain, I. G.; Hatton, L. R. Eur. Pat. Appl. 295 117, 1988; Chem. Abstr. 1990
, P 35845n.
4. Alia, J. M.; Backendorf, C. M. P. PCT Int. Appl. 075 903, 2003; Chem. Abstr. 2003
1. Scott, L. T.; Cheng, P.-C.; Bratcher, M. S. Eighth International Symposium on Novel Aromatic
Compounds, Victoria, British Columbia, Canada, July 19-24, 1992: Abstract No. 64.
2.2.17 Authors’ Biographies
(only required for reviews and accounts)
Each author should provide a photograph (portrait style, size 2 x 1.5 inches) and a short professional biography at the end of the manuscript.
2.4.1 Schemes, equations, and structure blocks
Scheme: depicts a series of chemical transformations containing chemical structures.
Equation: illustrates a simpler transformation with a single reaction arrow.
Structure Block: a collection of one or more numbered structures.
All graphics appear in the text immediately following the paragraph in which they are first mentioned.
For preparation of Schemes, Equations, and Structure Blocks, CS ChemDraw is the recommended drawing program, but ISISDraw may also be used (other programs are not acceptable). Do not insert the Schemes, Equations, and Structure Blocks as picture images
With ChemDraw or ISISDraw the following settings should be used:
Text font: Arial, 10 pt
Fixed length: 14.4 pt (0.508 cm, 0.2 in)
Bold width: 2.0 pt (0.071 cm, 0.0278 in)
Line width: 0.6 pt (0.021 cm, 0.0084 in)
Bond spacing: 18% of width
Hash spacing: 2.5 pt (0.088 cm, 0.0347 in)
Owing to the incomplete implementation of the MATH tag in some of the most popular browsers, efficient handling of mathematical equations is not possible. Therefore, authors should create their mathematical equations in a layout program of their choice and then save the equation as an image in jpg format.
Within Schemes, Equations, or Structure Blocks, individual structures may be numbered with boldface Arabic numerals and lower case letters, e.g. 32a, 32b
Schemes or chemical equations must be cited in the text using Arabic numerals, e.g. Scheme 1, Equation 1 etc.
Captions should be presented separately from the Scheme and Equation.
Synthesis of the known azide 6
from bromide 5
and sodium azide.
log k = (-2.62 ± 0.40)σ - (1.69 ± 0.17) (1)
When inserting Schemes, Equations, and Structure Blocks; do not use the float over text option
Diagrams, graphs, spectra, photographs, and any other illustrations should all be considered Figures.
Figures should be labeled sequentially with Arabic numerals as they appear, i.e. Figure 1
etc. together with a caption appearing separately below each Figure.
Figures should be included within the body of the manuscript close to the relevant text, but at the end of a paragraph.
Color art 300 dpi
Lowest energy conformations obtained for BP6 superimposed with the structure obtained experimentally by X-ray crystallography (yellow, C – grey, N – blue, O – red, P – violet, H – white.
3. Submission of Manuscript
3.1 Submission procedure
Manuscripts should be submitted via the Arkivoc online submission site www.arkat-usa.org/arkivoc-journal/online-submission/
. In order to submit, the corresponding author should login or register if using it for the first time. After login, click ‘Submit Manuscript’, read the disclaimer and proceed to Step 1. On the Step 1 form please enter your contact information and add co-authors' names as they appear in the paper masthead. You may add more than one co-author by using the ‘Add co-author’ button. After completing the first step click on ‘Proceed to step 2’. On the next form you will need to complete the Manuscript Title, select the Manuscript Type and the Issue to which the manuscript belongs. Please type in all the information. Copying and pasting may create invalid characters. To add Greek letters and format text to the title use the appropriated buttons. You must suggest the names of at least 3 referees for review. Step 3 will allow you to upload Manuscript, Graphical Abstract and Supporting Information files. We only accept Microsoft Word (.doc) file format. On Step 4 review your previously inputted information and submit your manuscript.
3.2 Refereeing procedure and editing of the manuscript
ii. Graphical Abstract
iii. Supplementary Material (optional or upon request by referees or the Scientific Editor).
iv. Suggestions for the names of three referees: the authors are required to provide the name, institution, and e-mail address of each referee.
All manuscripts approved by the Primary Review Committee will be reviewed by designated Arkivoc referees.
The Scientific Editor will receive reports from the referees. Upon receipt of referees' reports the Scientific Editor will make a decision: accepted, rejected or referred back to authors.
Proofs of the paper will be sent to the corresponding author for approval prior to publication on the website. Only minor changes can be made at the proof stage.
If in the opinion of the Publishing Editor authors request excessive proof corrections arising from the authors’ own errors in the original manuscript then the authors will be required to pay the full cost of the corrections, payable before publication, or the manuscript must be withdrawn and resubmitted.
3.3 Revision of manuscript
If a manuscript needs to be revised, the author should address ALL concerns and suggestions made by referees and/or the Scientific or Publishing editors.
The revised manuscript must be submitted to the Scientific Editor within 30 days. Failing this, the manuscript will be considered withdrawn. Resubmission of an unsatisfactorily revised manuscript may result in rejection. If another revision is needed, the time limit is two weeks.
3.4 Copyright agreement
In submitting a paper the authors accept the ARKAT USA, Inc. Copyright Agreement, which provides that copyright be held by the authors and ARKAT USA, Inc. be granted an irrevocable world-wide license.
4. Model Experimental Section
Melting points were measured on an Electrothermal 9100 apparatus and and IR spectra were recorded on a Shimadzu IR-460 spectrometer. 1
C, and 31
P NMR spectra were recorded at 500.1, 125.8, and 202.4 MHz respectively on a BRUKER DRX-500 AVANCE instrument with CDCl3
as solvent and TMS as internal standard. Mass spectra were recorded on a GCMS-QP5050A spectrometer operating at an ionization potential of 70 eV. Elemental analyses for C, H and N were obtained using a Heraeus CHN-O-Rapid analyzer. Activated acetylenic esters, phenanthridine, isoquinoline, succinimide, indole, 2-methylindole, 2-benzoxazolinone, 6-chloro- benzoxazolinone, carbazole, 3,6-dibromocarbazole, 1,3-dimethylbarbituric acid, acetylacetone and dibenzoylmethane were purchased from Fluka, (Buchs, Switzerland) and used without further purification.
General synthetic procedure, exemplified by ethyl (E)-3-(6-(2,5-dioxopyrrolidin-1-yl)phenanthridin-5(6H)-yl)acrylate (4a).
A solution of ethyl propiolate (0.1 g, 1 mmol) in CH2
(5 mL) was added dropwise over 10 min. to a magnetically stirred solution of phenanthridine (0.18 g, 1 mmol) and succinimide (0.09 g, 1 mmol) in CH2
(10 mL) at -10 o
C. After several hours stirring at ambient temperature, the reaction mixture solidified. Solvent was removed under reduced pressure, the brown residue washed with cold diethyl ether (2×5 mL) and recrystallized from a mixture of acetonitrile and acetone.
Colourless crystals, yield 92%, 0.35 g, mp 100-102 °C; IR (νmax
): 1707 and 1773 (C=O). 1
H NMR (500.1 MHz, CDCl3
1.29 (3H, t, 3JHH
7.2 Hz, OCH2
), 2.75 (4H, s, 2CH2
), 4.19 (2H, q, 3JHH
7.2 Hz, OCH2
), 5.85 (1H, d, 3JHH
13.6 Hz, N-CH=CH-CO2
), 7.13-8.09 (8Haro
, m, 8CH, phenanthridine), 8.60 (1H, d, 3JHH
13.6 Hz, N-CH=CH-CO2
), 9.03 (1H, s, NCHN). 13
C NMR (125.8 MHz, CDCl3
), 26.9 (OCH2
), 28.5 (2CH2
), 94.1 (NCHN), 115.8 (1C, N-CH=CH-CO2
), 120.7 (1C, N-CH=CH-CO2
), 121.1, 122.1, 122.5, 125.7, 126.1, 126.4, 126.9, 127.7, 127.8, 128.7, 130.1 and 152.2 (12C, phenanthridine), 174.8 (C=O, ester), 177.2 (2C=O, succinimide); Anal. Calcd for C22
(376.16): C, 70.18; H, 5.36; N, 7.44%. Found: C, 70.21; H, 5.31; N, 7.60%.
Ethyl (E)-3-(6-(1H-indol-1-yl)phenanthridin-5(6H)-yl)acrylate (4b).
Yellow crystals, yield 93%, 0.37 g, mp 138-140 °C; IR (νmax
): 1718 (C=O). 1
H NMR (500.1 MHz, CDCl3
1.18 (3H, t, 3JHH
7.1 Hz, OCH2
), 4.19 (2H, q, 3JHH
7.1 Hz, OCH2
), 5.45 (1H, d, 3JHH
16.6 Hz, N-CH=CH-CO2
), 6.25 (1H, d, 3JHH
3.5 Hz, N-CH=CH, indole), 6.31 (1H, d, 3JHH
3.5 Hz, N-CH=CH, indole), 7.14-8.03 (12Harom
, m, 12CH), 8.30 (1H, d, 3JHH
16.6 Hz, N-CH=CH-CO2
), 9.24 (1H, s, NCHN). 13
C NMR (125.8 MHz, CDCl3
), 25.7 (OCH2
), 63.8 (NCHN), 96.4 (1C, N-CH=CH-CO2
), 111.3, 113.3, 120.2 and 120.3 (4C, indole), 121.9, 122.6 and 122.5 (3C, phenanthridine), 123.3 and 124.3 (2C, indole), 125.6 (1C, N-CH=CH-CO2
), 125.7, 126.4 126.9,127.3, 127.8, 129.6 and 130.2 (7C, phenanthridine), 137.1 (1C, indole), 137.4 and 139.2 (2C, phenanthridine), 153.1 (1C, indole), 172.3 (C=O, ester). MS, m/z
(%) = 364 (M-Et and H, 13), 278 (C18
, 100), 204 (M-C8
Et and H, 48), 179 (C13
N, 60), 97 (C5
, 26); Anal. Calcd for C26
(394.17): C, 79.15; H, 5.62; N, 7.10%. Found: C, 78.98; H, 5.64; N, 7.18%.
[These instructions approved by the Arkivoc Steering Committee 14th September 2013]