Journal of Heterocyclic Chemistry

Cover image for Vol. 54 Issue 1

Edited By: Lyle W. Castle

Impact Factor: 0.685

ISI Journal Citation Reports © Ranking: 2015: 52/59 (Chemistry Organic)

Online ISSN: 1943-5193

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Editorial Policy

Every new manuscript is assigned a manuscript tracking number corresponding closely to the received date. To avoid confusion, authors should use the manuscript tracking number in all future correspondence with the editorial office. Manuscripts deemed suitable for the Journal of Heterocyclic Chemistry will be sent out for peer review. Manuscripts deemed unsuitable for any reason will be either rejected or sent back to the authors for revision. The Journal of Heterocyclic Chemistry is a peer-reviewed journal and as such takes the recommendations of selected reviewers very seriously; however, the final decision regarding the suitability of a submitted manuscript resides solely with the editor. Authors are expected to prepare their manuscripts according to high ethical standards. All scientific results reported within a manuscript must be those of the submitting authors or be suitably referenced or acknowledged such that those responsible for the results are given proper credit for their work. Submission of a manuscript to the Journal of Heterocyclic Chemistry indicates that this work is unique to the best of the authors' knowledge and that this information has only been submitted to this journal. Failure to adhere to high ethical standards will result in rejection of the manuscript and could lead to an author being barred permanently from publishing in the Journal of Heterocyclic Chemistry.

Manuscripts on any phase of heterocyclic chemistry will be considered for publication as articles, notes, communications to the editor, or reviews. Manuscripts describing the synthesis of novel new biologically active heterocyclic compounds along with the biological activity data are welcomed. All manuscripts except reviews require an abstract.

Articles must report the results of comprehensive research and will usually amount to at least four final printed journal pages. Shorter papers, usually classed as notes, are acceptable. Complete spectral characterization of all new compounds reported is required for publication in the Journal of Heterocyclic Chemistry. All new compounds must be subjected to combustion analysis for at least two elements (typically C and H) and values within 0.4% must be obtained.

Notes are simply smaller articles that are concise reports of completed projects. The requirements for notes are the same as those of articles. Manuscripts submitted as articles may in some cases be accepted as notes. As for articles, all new compounds must be adequately characterized by spectral data and combustion analysis.

Communications to the Editor may be of any length but should report new, important, and timely research for which rapid publication is warranted. We require that communications include procedures, compound preparation, and related data in sufficient detail that the work can be duplicated by an experienced chemist. Elemental analyses and spectral data supporting all new compounds are a requirement for publication and must he included as part of the submitted manuscript.

Reviews may be exhaustive or may be short, indicating only the highlights of a given area. It is wise to communicate with the editor in advance of preparation and/or submission to determine the timeliness of any given review.

Authors bear the sole responsibility for the contents of manuscripts and the accuracy of the data therein.

Manuscript Preparation

Manuscripts should be prepared using a modern word processing program, preferably MS Word. A single-column, double-spaced format should be used throughout the text. Manuscripts should be reasonably subdivided into sections and, if necessary, subsections. Please refer to any issue of this journal for examples. Twelve-point Times New Roman font should be used for all manuscripts. Greek letters and mathematical symbols (if any) should be typed in Symbol font; graphics for Greek letters and mathematical symbols should be avoided. Tables, figures, and schemes should be saved as separate files in the appropriate format described below.

Drawings, graphs, and illustrations should be submitted in electronic format. All digital art must be saved as TIFF or EPS files. (Note that the following file formats are not acceptable for printing: JPG, GIF, ONG, PCX, PNG, XBM, Word, Excel.) Please save all images separately. Images should be flattened prior to submission (i.e. files should not contain layers). All line art should have a resolution yielding 600–1200 dpi. Grayscale and color figures must have a resolution yielding 300 dpi. (To ensure that your digital graphics are suitable for print purposes, please go to Rapid Inspector at: This free, stand-alone software application will help you to inspect and verify illustrations right on your computer.) Art should be created or scaled to the size intended for print; no enlargement or reduction should be necessary. Digital art files should be cropped to remove non-printing borders. Files should be checked carefully for any type, lines, or other elements outside the illustration that are not intended for print. Such elements should be removed before submission. Image orientation should be the same as intended for print.

Chemical structures should be prepared in ChemDraw either 80mm (one column) or 170mm (two column) widths. However, the one-column format should be used whenever possible as this allows greater flexibility in the layout of the manuscript. Use this ChemDraw Download or use the following settings:

 Drawing settings    Text settings
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 fixed length  17 pt    
 bond width  2 pt  Preferences   
 line width  0.75 pt  units  points
 margin width  2 pt  tolerances  5 pixels
 hash spacing  2.6 pt    
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Authors using different structural drawing programs should choose settings consistent with those above. Compound numbers should be bold, but not atom labels or captions.

Tables should be created with the table-formatting feature in a Word document, not as graphics. Each data point must be incorporated into its own table cell. All tables must be numbered with Arabic numerals (e.g., Table 1) in the order in which they are mentioned in the text. Each table must have a short title describing the content. All table columns should have an explanatory heading. Notes within tables (if any) should be denoted by consecutive, lowercase, superscripted letters. Tables must be saved separately. The duplication of data in figures and tables should be avoided. The tables should be formatted to fit a single- or double-column printed width. Tables should clearly present data without reference to the manuscript text.

Literature references are to be numbered consecutively in order of appearance of the reference in the text and are to be placed at the end of the manuscript under the center heading REFERENCES AND NOTES. Reference numbers are to be placed in square brackets on the same line as the text. Authors are encouraged to include all pertinent references. All references should be compiled on a separate page at the end of the manuscript. Abbreviations of journal titles should conform to the practices of Chemical Abstracts Service Source Index (CASSI), though without italics or boldface, and periods or commas should not be used. Sample references follow.

Journal article:
[1] Luo, J.-K.; Castle, R. N. J Heterocycl Chem 1991, 28, 205.
[2] Sanghyi, Y. S.; Larson, S. B.; Robins, R. K.; Revenkar, C. R. J Chem Soc Perkin Trans 1 1990, 2943.

[3] Newkome, G. R.; Paudler, W. W. Contemporary Heterocyclic Chemistry; Wiley: New York, 1982; pp 107–109.

Book with multiple contributors:
[4] Schneller S. W. In Comprehensive Heterocyclic Chemistry; Potts, K. T., Ed.; Pergamon Press: Oxford, 1984; Vol 5, pp 847–904.

Patent citation (should include the Chemical Abstract reference):
[5] Van Schoor, A.; Schumann, W.; Lust, S.; Flemming, H. German Patent 1,141,487, 1962; Chem Abstr 1963, 58, 12470g.

References are the responsibility of the authors.

Nomenclature must conform to the recommendations set forth in the following sources: (1) Nomenclature of Organic Chemistry (IUPAC Blue Book), J. Rigaudy and S. P. Klesney, 1979 ed., Pergamon Press, Oxford; (2) Ring Systems Handbook, 2003 ed., Chemical Abstracts Service, 2540 Olentangy River Road, P.O. Box 3012, Columbus, OH 43210.


The experimental section should typically be located after the results and discussion section and should provide the reader with a clear and unambiguous description of the work reported. It should not be verbose, but should be sufficiently detailed that it is readily reproducible. The title of each experiment should include the chemical name of the compound and the assigned compound number. Either bold face Arabic or Roman numerals may be used for compound numbers; however, once one is chosen it must be used throughout the manuscript. At least one complete sentence per paragraph is encouraged but not required. Each previously unreported compound must be supported by adequate spectral data and elemental analyses for at least two elements agreeing with the theoretical value to within 0.4%. All elemental analytical data will be published. If suitable elemental analysis cannot be obtained, the authors should provide detailed reasons in the cover letter to the editor accompanying submission of the manuscript. Electronic copies of full spectral width NMR spectra (approximately -1 to 12 ppm) should be submitted along with the manuscript for compounds submitted without elemental analysis. Chemical names are preferred over chemical formulas and abbreviations in the discussion sections of the manuscript. Chemical formulas and limited use of abbreviations may be used in the experimental in place of chemical names. The following abbreviations, acronyms, and conventions may be used: g, mg, mL, L, mp, bp, tlc, hplc, gc, uv, ir, nmr, pmr, cmr, ms, hrms, lit, dec, mole, mmole, moles, mmoles, or mol, and mmol. The acronyms gc, uv, ir, nmr, pmr, cmr, ms, hrms may be either upper or lower case, but should be consistent throughout the manuscript. Other abbreviations are to be avoided, using in place of an abbreviation the complete word. All acronyms not listed above must be written out the first time it appears in the text. Extensive use of acronyms should be avoided. It is requested that simple punctuation be used in the experimental.

Examples of experimental procedures

3-(3′-Thienyl)-2-cyclohexen-1-one (15). A solution of 3.13 g (0.019 mole) of 3-bromothiophene (12) dissolved in 50 mL of dry ether was cooled to -78 °C. The 3-bromothiophene (12) was lithiated by slowly adding 12.4 mL of a 1.55 M solution of n-butyllithium inhexane. After the addition was complete, the solution was stirred at -78 °C for 30 min. A solution of 3.0 g (0.019 mole) of 1,4-dioxaspiro[4.5]decan-7-one in 25 mL of dry ether was added over a period of 20 min. The solution was allowed to warm to room temperature overnight. The solution was then neutralized with 10% aqueous ammonium chloride solution. The ether layer was separated, dried and the solvent was evaporated. The residue was then refluxed in aqueous 1.4 M hydrochloric acid for 1 h. The organic product was isolated by extraction with ether. The ether was dried (sodium sulfate) and evaporated to yield an oil which was crystallized from benzene-hexane as yellow needles, 1.4 g (41%), mp 100–102 °C; 1H nmr (deuteriochloroform): δ 2.0–3.0 (m, 6H), 6.3 (s, 1H), 7.3 (m, 2H), 7.5 (m, 1H); ms: m/z 180 (3.0), 179 (6.4), 178 (54), 150 (95), 122 (100), 121 (84), 39 (86). Anal. Calcd. for C10H10OS: C, 67.38; H, 5.65; S, 17.99. Found: C, 67.06; H, 5.75; S, 17.69.

General procedure for the reaction of tropone hydrazones 1-3 with phenylketene (8). All of these reactions were carried out under a nitrogen atmosphere. To a stirred and cooled (0 °C) solution of tropone benzoylhydrazone (11) (1.12 g, 5 mmoles) and triethylamine (0.61 g, 6 mmoles) in dry THF (15 mL), a solution (5 mL) of phenacetyl chloride (0.77 g, 6 mmoles) was added drop by drop for 10 min and the reaction mixture was allowed to stand at that temperature for an additional 30 min. After being warmed to room temperature gradually, the mixture was stirred overnight. The resultant triethylamine hydrochloride was filtered and the filtrate was evaporated in vacuo to give an oily residue. The residue was separated by column chromatography (silica gelchloroform) to give 9a and 10a in 25 and 9% yield, respectively.

1-Benzamido-1,2,3,3a-tetrahydro-2-oxo-3-phenyl-1-azaazulene (9a). This compound was obtained as colorless needles (isopropyl alcohol), mp 179–180 °C; ir: NH 3200, CO 1725, 1675 cm-1; 1H nmr: δ 3.12 (br, 1H, 3a-H), 3.86 (br d, 1H, 3-H, J = 5.7 Hz), 5.24 (dd, 1H, 4-H, J = 3.0, 9.0 Hz), 5.44 (d, 1H, 8-H, J = 6.3 Hz), 6.1-6.5 (m, 3H, 5-, 6-, and 7-H), 7.2-7.9 (m, 10H, phenyl protons), 9.3 ppm (br s, 1H, NH); ms: m/z 342 (M+), 224 (M+-PhCHCO), 119 (PhNCO+), 105, 77. Anal. Calcd. for C22H18N2O2: C, 77.17; H, 5.30; N, 8.18. Found: C, 77.16; H, 5.28; N, 8.35.

1,2,3,3a-Tetrahydro-2-oxo-1-phenylacetylbenzamido-3-phenyl-1-azaazulene (10a). This compound was obtained as colorless prisms (isopropyl alcohol), mp 158–159 °C; ir: CO 1755, 1730, 1705 cm-1; 1H nmr: δ 2.86 (br, 1H, 3a-H), 3.82 (br d, 1H, 3-H, J = 5.4 Hz), 4.15, 4.37 (2d, each, 1H, -CH2-, J = 15.3 Hz), 5.25 (dd, 1H, 4-H, J = 3.2, 9.6 Hz), 5.44 (d, 1H, 8-H, J = 6.3 Hz), 6.0–6.7 (in, 3H, 5- 6-, and 7-H), 7.1-7.7 ppm (m, 15H, phenyl protons); ms: m/z 460 (M+), 341 (M+-PhCH2CO), 224 (hydrazone 1+), 119 (PhNCO+), 105, 77. Anal. Calcd. for C30H24N2O3: C, 78.24; H, 5.25; N, 5.97. Found: C, 78.23; H, 5.25; N, 6.38.

Methyl 5-Cyanomethyl-1-(2-deoxy-b-D-erythropentofuranosyl)-pyrazole-4-carboxylate (14). To a solution of 9 (0.80 g, 1.54 mmoles) in dry methanol (25 mL) was added 1 M sodium methoxide in methanol (1.25 mL) and the mixture was stirred at room temperature for 1 h. The reaction mixture was neutralized with Dowex-50 H+ resin and filtered. The filtrate was evaporated to dryness. The residual semisolid was purified on a silica gel column (2.5 x 45 cm), prepacked in chloroform. Elution of the column with chloroform:methanol (19:1, v/v) gave a homogeneous residue, which was crystallized from aqueous ethanol to yield 0.17 g (37%), mp 118–120 °C; ir (potassium bromide): 1700 (C=O), 2260 (C&tbond;N), 3400 (OH) cm-1; uv: (pH 1): λ max 218 nm (ε 11,000); (pH 7): λ max 218 nm (ε 11,100); (pH 11): λ max 224 nm (ε 10,200); 1H nmr (DMSO-d6): δ 3.82 (s, 3, CO2CH3), 4.40 (s, 2, CH2), 6.16 (t, 1, peak width 14.5 Hz, C1′H), 8.18 (s, 1, C3H), and other sugar protons. Anal. Calcd. for C12H15N3O5 (281.17): C, 51.24; H, 5.33; N, 14.94. Found: C, 50.99; H, 5.43; N, 14.80.

5-Amino-1-[4-methylsulfonyl)phenyl]-1H-pyrazole-4-carbonitrile (5b). A solution of 50.0 g (0.268 mole) of 4-methylsulfonyi)-phenylhydrazine (3b) and 34.3 g (0.281 mole) of ethoxymethylenemalononitrile (4) in 250 mL of ethanol was heated at reflux. A precipitate was observed after 15 min. After 15 h, the mixture was cooled and the yellow solid was collected and air-dried to yield 51.4 g (73%) of 5b, mp 236–238 °C; ir (Nujol): 3450, 3315 and 3170 (NH), 2225 (CN), 1635 cm-1; 1H nmr (dimethyl sulfoxide d6): δ 8.11 (d, J = 8 Hz, 2H, phenyl), 7.89 (s, 1H, C3-H), 7.84 (d, J = 8 Hz, 2H, phenyl), 6.94 (broad s, 2H, NH, deuterium oxide exchangeable), 3.25 (s, 3H, CH3); ms: (70 eV, electron impact) m/z 262 (molecular ion). Anal. Calcd. for C11H10N4O2S: C, 50.37; H, 3.84; N, 21.36. Found: C, 50.40; H, 3.87; N, 21.57.

3-Methoxy-4H-pyran-4-one-2-carboxaldehyde (1). 2-Hydroxymethyl- 3-methoxy-4H-pyran-4-one (700 mg) was dissolved in 50 mL of dichloromethane. Barium manganate (7.5 g) was ground to a fine powder and added immediately to the dichloromethane solution. The mixture was stirred with the aid of a magnetic stirrer for 2 h at room temperature. Inorganic by-products were removed by filtration of the reaction mixture through Celite. The Celite was washed with dichloromethane; the latter solution was added to the dichloromethane filtrate previously obtained. Evaporation of dichloromethane in vacuo gave a white residue, which was recrystallized from cyclohexane to give 635 mg (92%) of 3-methoxy-4H-pyran-4-one-2-carboxaldehyde (1), mp 85-86 °C; 1H nmr (deuteriochloroform): δ 4.16 (s, 3H, OCH3), 6.43 (d, 1H, H5), 7.73(d, 1H, H6), 10.14 (s, 1H, CHO); ir (potassium bromide): 3100 (CH), 1695 (aldehyde CO), 1655 (pyrone CO), 1575, 1460, 1430, 1395, 1275, 1225, 1200, 1175, 1050, 950, 850, 830, 750, 640 cm-1. Anal. Calcd. for C7H6O4: C, 54.55; H, 3.92. Found: C, 54.58; H, 3.91.

Important points regarding experimental procedures

1. The requirement of a sufficiently detailed experimental description to enable an experienced chemist to repeat the experiment successfully.
2. The requirement of the bold chemical name and assigned compound number at the beginning of each experimental procedure.
3. The manner in which physical, spectral, and analytical data should be reported. The above examples show that typically the overall order for presenting data should be: color/appearance, mp, uv, ir, 1H nmr, 13C nmr, ms/hrms, and finally elemental analysis.
4. The manner in which general procedures are presented. In the case of a general procedure for the synthesis of two or more compounds, this must be followed by a bold chemical name and the assigned compound number for each compound prepared by the general procedure followed by the physical spectral and analytical data for that compound.


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Electronic Proofing

In order to expedite the publication and online posting of articles in Wiley Online Library, the Journal of Heterocyclic Chemistry now offers electronic proofing. Corresponding authors will be sent page proofs (and paperwork, such as reprint order forms) in PDF format via e-mail. Please follow the instructions in the e-mail; contact names and numbers are given for questions, problems, or if an author wishes to receive a paper proof. A fax cover form with the Production Editor’s information is also provided for authors to fax their corrections.

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