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 Sa⋯O interaction / Sadchikova E.V., Bakulev V.A., Subbotina J.O., Privalova D.L., Dehaen W., Van Hecke K., Robeyns K., Van Meervelt L., Mokrushin V.S. // Tetrahedron. - 2013. - V. 69, l. 34. - P. 6987-6992.

ISSN:

00404020

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 Sa⋯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-tetrafluorobenzoyl)iminoimidazo(pyrazolo)[5,1-d][1,2,3, 5]thiatriazines. © 2013 Elsevier Ltd. All rights reserved.

Author keywords:

Covalence ratio factor; Cycloaddition; Diazoazoles; Nonbonded; Sa⋯O interaction; Thiatriazines

Index keywords:

imidazole derivative; isothiocyanic acid derivative; oxygen; pyrazole derivative; pyrrole derivative; sulfur; triazine derivative; article; carbon nuclear magnetic resonance; chemical bond; crystal st

DOI:

10.1016/j.tet.2013.06.062

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https://www.scopus.com/inward/record.uri?eid=2-s2.0-84880137100&doi=10.1016%2fj.tet.2013.06.062&partnerID=40&md5=f2d37a4c7f7ab7490007dcc10590dc5d

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Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-84880137100&doi=10.1016%2fj.tet.2013.06.062&partnerID=40&md5=f2d37a4c7f7ab7490007dcc10590dc5d
Affiliations	TOS Department, Ural Federal University, Mira str. 19, 620002 Yekaterinburg, Russian Federation; Department of Chemistry, University of Leuven, B-3001 Leuven, Belgium; I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, S. Kovalevskaya Str. 20, 620219 Yekaterinburg, Russian Federation
Author Keywords	Covalence ratio factor; Cycloaddition; Diazoazoles; Nonbonded; Sa⋯O interaction; Thiatriazines
Chemicals/CAS	oxygen, 7782-44-7; sulfur, 13981-57-2, 7704-34-9
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Correspondence Address	Bakulev, V.A.; TOS Department, Ural Federal University, Mira str. 19, 620002 Yekaterinburg, Russian Federation; email: v.a.bakulev@ustu.ru
CODEN	TETRA
Language of Original Document	English
Abbreviated Source Title	Tetrahedron
Source	Scopus