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JOURNAL OF HETEROCYCLIC CHEMISTRY

INSTRUCTIONS TO AUTHORS

Online Submission

The Journal of Heterocyclic Chemistry is pleased to offer web-based submission and peerreview. To submit your manuscript online, go to http://mc.manuscriptcentral.com/jhetchem.

Prepare your manuscript and illustrations in the appropriate format, according to theinstructions given below. Please also be sure that your paper conforms to the scientific

and style instructions of the journal.

If you are unsure of your password, enter your e-mail address in the Password Helpbox. If you have an account, a temporary password will be e-mailed to you to gain

access to your account. If you do not have an account, you can create one for yourself in

the system at the submission site by clicking on the Create Account button.Subsequently, to monitor the progress of your manuscript throughout the review process,

log in to Manuscript Central periodically and check your Author Center. When you are ready to submit your manuscript, let the system guide you through the

submission process. Online help is available to you at all times during the process by

clicking "Get Help Now" in the upper right hand corner of the screen. You are also able

to exit and re-enter the submission process at any stage by clicking on Manuscripts inDraft in your Author Center and revising your information. When all steps in the

submission process are complete, click the Submit button located at the bottom right

hand corner of the submission screens last page.

All submissions are kept strictly confidential.

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 allfuture 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 ofselected 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 acknowledgedsuch 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 bestof 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 HeterocyclicChemistry.


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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 ofnovel 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 combustionanalysis 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. Therequirements 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 my length but should report new, important, and

timely research for which rapid publication is warranted. We require that communicationsinclude procedures, compound preparation, and related data in sufficient detail that the work canbe 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 determinethe 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 allmanuscripts. 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 forprinting: 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 6001200 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: http://rapidinspector.cadmus.com/zwi/index.jsp. This free, stand-


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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 orreduction 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 and reaction

schemes should be drawn with an appropriate drawing program. (Technical guidance andadvised ChemDraw and ISIS/Draw settings are available from the editor.) All files must be

saved in TIFF (.tif) or EPS (.eps) format and may not be submitted in native application formats.Poor quality or improperly prepared artwork will lead to delay in publication.

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 explanatoryheading. 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. Tablesshould 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 headingREFERENCES 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 journaltitles should conform to the practices ofChemical Abstracts Service Source Index (CASSI),

though without italics or bold face, and periods or commas should not be used. Samplereferences 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.

Book:

[3] Newkome, G. R.; Paudler, W. W. Contemporary Heterocyclic Chemistry; Wiley: New

York, 1982; pp 107109.

Book with multiple contributors:

[4] Schneller S. W. In Comprehensive Heterocyclic Chemistry; Potts, K. T., Ed.; PergamonPress: Oxford, 1984; Vol 5, pp 847904.

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.


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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, 1979ed., Pergamon Press, Oxford; (2) Ring Systems Handbook, 2003 ed., Chemical Abstracts Service,

2540 Olentangy River Road, P.O. Box 3012, Columbus, OH 43210.

Experimental

The experimental section should typically be located after the results and discussion section andshould 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 assignedcompound 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 unreportedcompound 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 detailedreasons in the cover letter to the editor accompanying submission of the manuscript. Electroniccopies 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 themanuscript. 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. Otherabbreviations 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 useof acronyms should be avoided. It is requested that simple punctuation be used in theexperimental.

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 Msolution ofn-

butyllithium inhexane. After the addition was complete, the solution was stirred at -78 C for 30min. 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 Mhydrochloric 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 whichwas crystallized from benzene-hexane as yellow needles, 1.4 g (41%), mp 100102 C;

1H nmr

(deuteriochloroform): 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.


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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 (0C) 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 temperaturefor 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 wasevaporated 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 179180 C; ir: NH 3200, CO 1725, 1675

cm-1

; 1H nmr: 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 158159 C; ir: CO 1755,

1730, 1705 cm-1; 1H nmr: 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),6.06.7 (in, 3H, 5- 6-, and7-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 of9 (0.80 g, 1.54 mmoles) in dry methanol (25 mL) was added 1 Msodium

methoxide in methanol (1.25 mL) and the mixture was stirred at room temperature for 1 h. Thereaction 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%), mp118-120 C; ir (potassium bromide): 1700 (C=O), 2260 (CN), 3400 (OH) cm

-1; uv: (pH 1):

max 218 nm ( 11,000); (pH 7): max 218 nm ( 11,100); (pH 11): max 224 nm ( 10,200);1H

nmr (DMSO-d6): 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) ofethoxymethylenemalononitrile (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%) of5b, mp 236-238 C; ir (Nujol): 3450, 3315 and 3170 (NH),

2225 (CN), 1635 cm-1

; 1H nmr (dimethyl sulfoxided6): 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-


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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 filtratepreviously 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): 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 anexperienced chemist to repeat the experiment successfully.

2. The requirement of the bold chemical name and assigned compound number at thebeginning of each experimental procedure.

3. The manner in which physical, spectral, and analytical data should be reported. Theabove 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.

Electronic Proofing

In order to expedite the publication and online posting of articles in Wiley InterScience, theJournal 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. Pleasefollow 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

Editors information is also provided for authors to fax their corrections.

??? Production Questions ???

Glenn BeckPhone: 201-748-8659

Fax: 201-748-6052

E-mail: [email protected]

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