The reaction of pyrrole-2-carbonitriles with hydrazine hydrate in the presence of hydrazine dihydrochloride (ethylene glycol, 130-132°С, 1-2 h, argon atmosphere) affords the hitherto unknown 3,5-bis(1H-pyrrol-2-yl)-4H-1,2,4-triazol-4-amines in up to 86% yield.

Secondary phosphine oxides reacted with 1-alkanoyl-2-phenylacetylenes in chemoselective fashion under mild conditions (20°C, THF) in the absence of a catalyst (diphenylphosphine oxide) or in the presence of potassium hydroxide [bis(2-phenylethyl)phosphine oxide] to give 1-alkyl-1-diphenyl(or 2-phenylethyl)-phosphoryl-3-phenylprop-2-yn-1-ols in up to 96% yield. The reaction of diphenylphosphine oxide with 1-alkanoyl-2-phenylacetylenes in the system KOH-THF (20°C) afforded not only adducts at the carbonyl group but also products of double α,β-addition at the triple bond, 2,3-bis(diphenylphosphoryl)-3-phenylpropan-1-ones.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

3-Phenylamino-5-phenylimino-1,2,4-dithiazole reacted with 1-acyl-2-phenylacetylenes in ethanol or toluene on heating (78–80°C, 1 h) in chemo- and regioselective fashion to give previously unknown N -[5-acyl-3,4-diphenyl-1,3-thiazol-2(3 H )-ylidene]- N ′-phenylthioureas (yield 57–60%). The structure of N -[5-benzoyl-3,4-diphenyl-1,3-thiazol-2(3 H )-ylidene]- N ′-phenylthiourea was proved by X-ray analysis.

Thiocarbonohydrazones derived from aromatic aldehydes reacted with 4-phenylbut-3-yn-2-one in aqueous acetic acid (20°C, 2 h) to produce previously unknown N″-[(E-s-cis)-arylmethylidene]-N″′-[(Z-s-trans)-1-methyl-3-phenylprop-2-yn-1-ylidene]thiocarbonohydrazides with high chemo-, regio-, and stereoselectivity. The steric structure of N″-[(E-s-cis)-benzylidene]-N″′-[(Z-s-trans)-1-methyl-3-phenylprop-2-yn-1-ylidene]thiocarbonohydrazide in crystal and in solution was studied by X-ray analysis and IR and NMR spectroscopy.

3-Bromo-1-phenylprop-2-yn-1-one reacted with 1-benzylidenethiocarbonohydrazones in acetic acid or acetonitrile at room temperature (reaction time 3 h) to give in good yields the corresponding benzaldehyde N′-(5-benzoylmethyl-1,3,4-thiadiazol-2-yl)hydrazone hydrobromides which were converted into the free bases by treatment with aqueous ammonia.

1-Acetyl-2-phenylacetylene reacts with thiocarbohydrazide under mild conditions to afford exclusively N2-(Z-s-trans), N3-(Z-s-cis)- bis(1-methyl-3-phenyl-2-propynylidene)carbonothioic dihydrazide in high yield (up to 92%); the structure of the compound has been confirmed by IR and NMR spectroscopy and X-ray analysis.

1-Benzoyl-2-phenylacetylene reacted with N-(carbamimidoyl)thiourea in glacial acetic acid saturated with 20% HBr to give (4,6-diphenyl-2H-1,3-thazin-2-ylidene)guanidine hydrobromide. The reaction of the same compounds in anhydrous ethanol in the presence of sodium ethoxide led to the formation of N-(4,6-diphenylpyrimidin-2-yl)thiourea. Bis(3-oxo-1,3-diphenylprop-1-en-1-yl) sulfide and 1-benzoyl-2-ethylsulfanyl-2-phenylethylene were isolated in the reactions of 1-benzoyl-2-phenylacetylene with N-(carbamimidoyl)thiourea and N-(carbamimidoyl)-S-ethylisothiuronium bromide, respectively, in anhydrous methanol.

The reaction of 1-aroyl-2-phenylacetylenes with thiocarbonohydrazide and benzaldehyde thiocarbohydrazone in acetic acid-water or ethanol-water systems with the reagents in an equimolar ratio leads to the selective formation of 1-carbothiohydrazinoyl-5-hydroxy-3-phenyl-5-R-2-pyrazolines. Ring-chain tautomerism involving the enamine and hydrazone forms was detected for solutions of the pyrazolines (with R = 2-thienyl) in DMSO.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

ChemInformVolume 36, Issue 42 Heterocyclic Compounds 1-Benzoyl-2-phenylacetylene and 1-Methyldithiobiuret as Key Compounds in the Synthesis of N-Methyl-N′-(4,6-diphenyl-1,3-thiazin-2-ylidene)thiourea (IV). T. E. Glotova, T. E. Glotova A. E. Favorsky Inst. Chem., Sib. Branch, Russ. Acad. Sci., Irkutsk 664033, RussiaSearch for more papers by this authorM. Yu. Dvorko, M. Yu. Dvorko A. E. Favorsky Inst. Chem., Sib. Branch, Russ. Acad. Sci., Irkutsk 664033, RussiaSearch for more papers by this authorA. I. Albanov, A. I. Albanov A. E. Favorsky Inst. Chem., Sib. Branch, Russ. Acad. Sci., Irkutsk 664033, RussiaSearch for more papers by this author T. E. Glotova, T. E. Glotova A. E. Favorsky Inst. Chem., Sib. Branch, Russ. Acad. Sci., Irkutsk 664033, RussiaSearch for more papers by this authorM. Yu. Dvorko, M. Yu. Dvorko A. E. Favorsky Inst. Chem., Sib. Branch, Russ. Acad. Sci., Irkutsk 664033, RussiaSearch for more papers by this authorA. I. Albanov, A. I. Albanov A. E. Favorsky Inst. Chem., Sib. Branch, Russ. Acad. Sci., Irkutsk 664033, RussiaSearch for more papers by this author First published: 28 September 2005 https://doi.org/10.1002/chin.200542182Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume36, Issue42October 18, 2005 RelatedInformation

ChemInformVolume 36, Issue 10 Heterocyclic Compounds Synthesis and Reactions of 2-Benzoylmethyl-2-phenyl-4,6-di(phenylimino)-5H-1,3,5-dithiazinium Perchlorate. T. E. Glotova, T. E. Glotova A. E. Favorsky Inst. Chem., Sib. Branch, Russ. Acad. Sci., Irkutsk 664033, RussiaSearch for more papers by this authorN. I. Protsuk, N. I. Protsuk A. E. Favorsky Inst. Chem., Sib. Branch, Russ. Acad. Sci., Irkutsk 664033, RussiaSearch for more papers by this authorM. Yu. Dvorko, M. Yu. Dvorko A. E. Favorsky Inst. Chem., Sib. Branch, Russ. Acad. Sci., Irkutsk 664033, RussiaSearch for more papers by this authorA. I. Albanov, A. I. Albanov A. E. Favorsky Inst. Chem., Sib. Branch, Russ. Acad. Sci., Irkutsk 664033, RussiaSearch for more papers by this author T. E. Glotova, T. E. Glotova A. E. Favorsky Inst. Chem., Sib. Branch, Russ. Acad. Sci., Irkutsk 664033, RussiaSearch for more papers by this authorN. I. Protsuk, N. I. Protsuk A. E. Favorsky Inst. Chem., Sib. Branch, Russ. Acad. Sci., Irkutsk 664033, RussiaSearch for more papers by this authorM. Yu. Dvorko, M. Yu. Dvorko A. E. Favorsky Inst. Chem., Sib. Branch, Russ. Acad. Sci., Irkutsk 664033, RussiaSearch for more papers by this authorA. I. Albanov, A. I. Albanov A. E. Favorsky Inst. Chem., Sib. Branch, Russ. Acad. Sci., Irkutsk 664033, RussiaSearch for more papers by this author First published: 08 February 2005 https://doi.org/10.1002/chin.200510152Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume36, Issue10March 8, 2005 RelatedInformation

2-Benzoylmethylene-1,3,5-dithiazinium hydrobromides were prepared in high yield by the reaction of 1-bromo-2-benzoylacetylene with 2,4-dithiobiurete and its mono- and disubstituted derivatives in glacial AcOH. The ability of the compounds synthesized to undergo further chemical transformations has been studied.

[4-Phenyl-2H-1,3-thiazin]-2-ylideneguanidinium perchlorate or acetoxytrifluoroborate respectively was obtained from the reaction of benzoylacetylene with N-amidinothiourea in glacial AcOH in the presence of an equimolar quantity of HClO4 or BF3⋅Et2O. These compounds underwent hydrolysis at the amidine unit on treatment with acid or base. For example, the perchlorate on heating in HClO4 was converted into 2-imino-4-phenyl-2H-1,3-thiazinium perchlorate, while treatment with aqueous NaOH in DMSO gave the free base - 6-phenyl-1,2-dihydropyrimidine-2-thione.

The reactions of benzoylacetylene, propiolic acid, and methyl propiolate with 2,4-dithiobiuret and 1-substituted and 1,5-disubstituted 2,4-dithiobiurets in glacial AcOH in the presence of HClO 4 or BF 3 ·Et 2 O were used to obtain 2-substituted 4-amino-6-imino-1,3,5-dithiazinium perchlorates or trifluoroborates, respectively.

Reaction of benzoylacetylene with 1,5-diphenyldithiobiuret in glacial AcOH in the presence of equimolar amounts of HClO4 leads exclusively to 2-benzoylmethyl-4,6-di(phenylimino)-1,3,5-dithiazinium perchlorate. In MeOH, benzene, and MeCN medium, the reaction proceeds nonselectively and a mixture is formed that includes 2-benzoylmethyl-4,6-di(phenylimino)-1,3,5-dithiazine, 2-benzoylmethyl-4-benzoylvinylthio-3-phenyl-6-phenylimino-1,3,5-thiadiazine, 2-benzoylmethyl-4,6-di-(thiocarbonyl)-1,3-diphenyl-1,3,5-triazine, and N-benzoylvinyl-N'-phenylthiourea.

The reaction of thiourea with l-acyl-2-bromoacetylenes in AcOH in the presence of BF3·Et2O affords 2-amino-4-phenyl(2-thienyl)-1,3-thiazine-6-thiones in high yields.

The reactions of terminal acylacetylenes with thiocarbohydrazones give 2-(2-acyl-vinyl)thiocarbohydrazones or 2,2-bis(2-acylvinyl)thiocarbohydrazones depending on the reagent ratio. Benzoylacetylene reacts with thiocarbohydrazone of p-dimethylaminobenzaldehyde to form S-[2-(p-dimethylaminobenzoyl)vinyl]isothiocarbodihydrazone.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Substituted thioureas react with 1-bromo-2-benzoylacetylene in various solvents at 20°C to give the corresponding N -substituted 4-benzoyl-2-(R-imino)-3-R′-thiazolium bromides.