Dithiobiuretes in reactions with electrophilic acetylenes. New derivatives of 1,3,5-dithiazines,-thiadiazines and-triazines as the products of competing reactions of nucleophilic cycloaddition-Reference-Cited by-同舟云学术

Dithiobiuretes in reactions with electrophilic acetylenes. New derivatives of 1,3,5-dithiazines,-thiadiazines and-triazines as the products of competing reactions of nucleophilic cycloaddition

Published:2003-09-01 Issue:3 Volume:1 Page:222-232
ISSN:2391-5420
Container-title:Open Chemistry
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Author:

Glotova Tatýana¹,Protsuk Nadezhda¹,Albanov Alexander¹,Lopyrev Valentin¹,Dolgushin Gennadii¹

Affiliation:

1. 1A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of Russian Academy of Sciences, 1 ul. Favorsky, Irkutsk, Russian Federation

Abstract

AbstractThe nucleophilic addition of 2,4-dithiobiurete, 1- and 1,4-substituted 2,4-dithiobiuretes (2 a-e) with benzoylacetylene (1) has been studied. 2-(Benzoylmethyl)-4-(R1-imino)-6-(R2-imino)dihydro-4H-1,3,5-dithiazinium perchlorates (3 a-e) are obtained in glacial acetic acid (AcOH) in the presence of equimolar quantities of HClO4. The reaction of benzoylacetylene with 1,5-diphenyl-2,4-dithiobiurete in either of MeOH, C6H6, or MeCN solvents proceeds non-selectively to give a mixture of products such as 2-(benzoylmethyl)-4,6-di(phenylimino)dihydro-4H-1,3,5-dithiazine (5), 2-(benzoylmethyl)-4-(β-benzoylvinyl)thio-3-phenyl-6-(phenylimino)-3,6-dihydro-2H-1,3,5-thiadiazine (8), 2-(benzoylmethyl)-1,3-diphenylhexahydro-1,3,5-triazine-4,6-dithione (7) and N-(β-benzoylvinyl)-N-phenylthioureas (6).

Publisher

Walter de Gruyter GmbH

Subject

Materials Chemistry,General Chemistry

Link

http://link.springer.com/content/pdf/10.2478/BF02476225.pdf

Reference10 articles.

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4. M.S. Chande and N.P. Shetgiri: “Reaction of Ethylchloroformate with 1-Alkyl/Aryl-2,4-dithiobiurets in Presence of Ketohes”, J. Indian Chem. Soc., Vol. 67, (1990), pp. 849–852.

5. A.S. Nakhmanovich, T.E. Glotova, T.N. Komarova, V.A. Lopyrev: “A New Route of Synthesis of Substituted 5,6-Dihydro-1,3,5-dithiazinium hydrobromides by the Reaction of 1-Acyl-2-bromoacetylenes with Dithiobiurete”, Khim. Geterotsikl. Soed., No. 3, (1998), pp. 417–418 (Rus).

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