Unexpected result for the acylation of arylhydrazonoethanethioamides / Bolgova Anastasiya I.,Lugovik Kseniya I.,Subbotina Julia O.,Slepukhin Pavel A.,Bakulev Vasiliy A.,Belskaya Nataliya P. // TETRAHEDRON. - 2013. - V. 69, l. 35. - P. 7423-7429.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

The acylation of arylhydrazonoethanethioamides containing primary amino group did not yield acylthioamides as expected. Surprisingly, the cyclic 5-acylimino-2,5-dihydro-1,2,3-thiadiazoles were obtained. The formation of thiadiazoles in this reaction was explained by the higher ability of arylhydrazono-N-acylthioacetamide intermediates to be oxidized comparing to their precursors. The presence of pseudobicyclic aromatic structure in the reaction product was a main factor favoring the formation of 1,2,3-thiadiazole ring. (C) 2013 Elsevier Ltd. All rights reserved.

Author keywords:

Arylhydrazonoethanethioamide; Acylation; 1,2,3-Thiadiazole; Oxidation; Thiapentalene INDEPENDENT CHEMICAL-SHIFTS; INTRAMOLECULAR CYCLIZATION; OXIDATIVE CYCLIZATION; O INTERACTION; DERIVATIVES; NUCLEUS; SYSTEMS; NICS

DOI:

10.1016/j.tet.2013.06.071

Web of Science ID:

ISI:000322557500031

Соавторы в МНС:

Другие поля

Поле	Значение
Month	SEP 2
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	INDEPENDENT CHEMICAL-SHIFTS; INTRAMOLECULAR CYCLIZATION; OXIDATIVE CYCLIZATION; O INTERACTION; DERIVATIVES; NUCLEUS; SYSTEMS; NICS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	n.p.belskaya@ustu.ru
ResearcherID-Numbers	Belskaya, Nataliya/S-3953-2017 Subbotina, Julia/L-7131-2016
ORCID-Numbers	Belskaya, Nataliya/0000-0002-2509-7916 Subbotina, Julia/0000-0002-2227-0787
Funding-Acknowledgement	Russian Foundation for Basic Research {[}11-03-00579\_a, 10-03-96084-r\_ural\_a, 12-03-31574 mol\_a]
Funding-Text	The authors thank the Russian Foundation for Basic Research for financial support (grant RFBR \# 11-03-00579\_a, RFBR \# 10-03-96084-r\_ural\_a, RFBR \# 12-03-31574 mol\_a). J.O.S. personally thanks Prof. Arvi Rauk (University of Calgary, Canada) for assistance. J.O.S. also thanks Compute Canada-Calcul Canada and Western Canada Research Grid for provided computational resources.
Number-of-Cited-References	36
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	16
Journal-ISO	Tetrahedron
Doc-Delivery-Number	193KA