Synthesis and structure of new imidazo- and pyrazolo{[}5,1-d]{[}1,2,3,5] thiatriazines based on the reaction of diazoazoles with acyl isothiocyanates controlled by S center dot center dot center dot O interaction / Sadchikova Elena V.,Bakulev Vasiliy A.,Subbotina Julia O.,Privalova Darya L.,Dehaen Wim,Van Hecke Kristof,Robeyns Koen,Van Meervelt Luc,Mokrushin Vladimir S. // TETRAHEDRON. - 2013. - V. 69, l. 34. - P. 6987-6992.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

5-Diazoimidazoles and 5-diazopyrazoles have been shown to react with acyl isothiocyanates yielding the imidazo- and pyrazolo{[}5,1-d]{[}1,2,3,5]thiatriazines stabilized by a nonbonded S center dot center dot center dot O interaction. In contrast to acyl isothiocyanates, alkyl-, aryl-, and arylsulfonyl isothiocyanates do not react with 5-diazoazoles. The nature and the strength of stabilizing intramolecular interaction between non-bonded S and O atoms have been studied by X-ray analysis for mono crystals and DFT calculations for selected azolo{[}5,1-d] {[}1,2,3,5]thiatriazines. The interaction was described in terms of Weinhold covalence ratio factors, NBO, and AIM schemes. The reaction discovered was used to develop an efficient approach toward the new 8-substituted 4-ethoxycarbonylimino-4-benzoyl- and 4-(3,4,5,6-tetrafluorobenzoy)iminoimidazo(pyrazolo){[}5,1-d]{[}1,2,3,5]t hiatriazines. (C) 2013 Elsevier Ltd. All rights reserved.

Author keywords:

Cycloaddition; Diazoazoles; Thiatriazines; Nonbonded S center dot center dot center dot O interaction; Covalence ratio factor ANTITUMOR DRUG TEMOZOLOMIDE; ONE-POT SYNTHESIS; CYCLOADDITION; ROUTE

DOI:

10.1016/j.tet.2013.06.062

Web of Science ID:

ISI:000322098000006

Соавторы в МНС:

Другие поля

Поле	Значение
Month	AUG 26
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	ANTITUMOR DRUG TEMOZOLOMIDE; ONE-POT SYNTHESIS; CYCLOADDITION; ROUTE
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	v.a.bakuiev@ustu.ru
Funding-Acknowledgement	Russian Foundation for Basic Research {[}10-03-00897-a, 12-03-31574 mol\_a]; FWO-Vlaanderen; Ministerie voor Wetenschapsbeleid; KU Leuven
Funding-Text	V.A.B. thanks Russian Foundation for Basic Research (grants no. 10-03-00897-a). W.D. thanks the FWO-Vlaanderen, the Ministerie voor Wetenschapsbeleid and the KU Leuven for continuing financial support. 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. J.O.S. thanks Russian Foundation for Basic Research (grants no. 12-03-31574 mol\_a).
Number-of-Cited-References	42
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	14
Journal-ISO	Tetrahedron
Doc-Delivery-Number	187DV