Reaction of 5-halo-1,2,3-thiadiazoles with arylenediamines as a new approach to tricyclic 1,3,6-thiadiazepines / Volkova NN,Tarasov EV,Van Meervelt L,Toppet S,Dehaen W,Bakulev VA // JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1. - 2002. - V. , l. 13. - P. 1574-1580.

ISSN/EISSN:

1472-7781 / нет данных

Type:

Article

Abstract:

A multistep reaction of 5-halo-1,2,3-thiadiazoles and 1,2-phenylenediamines provides a new route to fused 1,3,6-thiadiazepines. The overall process consists of the known stepwise formation of 5-{[}1-(2-aminophenyl)-1,2,3-triazol-5-ylsulfanyl]-1,2,3-thiadiazole, and a novel ring transformation which involves the Smiles and Dimroth rearrangements followed by an intramolecular nucleophilic substitution of the thiol group, affording di{[}1,2,3]triazolo{[}1,5-a:5',1'-d]-{[}3,1,5]benzothiadiazepines. The influence of the substituents on the 1,2,3-thiadiazole and phenyl rings on this reaction was discussed.

Author keywords:

REARRANGEMENT; DERIVATIVES; AGENTS

DOI:

10.1039/b203072a

Web of Science ID:

ISI:000176467500010

Соавторы в МНС:

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Другие поля

Поле	Значение
Publisher	ROYAL SOC CHEMISTRY
Address	THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
Language	English
Keywords-Plus	REARRANGEMENT; DERIVATIVES; AGENTS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Number-of-Cited-References	27
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	3
Journal-ISO	J. Chem. Soc.-Perkin Trans. 1
Doc-Delivery-Number	567CH