Tandem pseudopericyclic processes in the cyclization ofα-diazonitriles to 5-halo-1,2,3-triazoles. Scope and limitations / Bakulev V.A., Morzerin Y.Yu., Shafran Y.Yu., Mokrushin V.S. // Arkivoc. - 2002. - V. 2002, l. 8. - P. 166-179.

ISSN:

14246376

Type:

Article

Abstract:

A series of α-carbonyl diazoacetonitriles has been synthesized and subjected to reaction with hydrogen halides. The scope and limitations of this reaction for preparing 5-halo-1,2,3-triazoles have been determined. The experimental energy of this cyclization is 15-20 Kcal mol-1. A mechanism of this reaction consists of two steps-addition of HHa1 to α-carbonyl diazonitriles via a pseudopericyclic group transfer reaction leads to formation of intermediate α-diazohaloimines which in subsequent hetero-electrocyclic reactions afford 5-halo-1,2,3-triazoles. Indeed, the cyclization of α-carbonyl diazonitriles is a series of tandem pseudopericyclic processes.

Author keywords:

α-carbonyl diazoacetonitriles; 5-halo-1,2,3-triazoles; Tandem pseudopericyclic processes

Index keywords:

5 bromo 1,2,3 triazole 4 carboxamide; 5 bromo 4 4 methoxyphenylcarbonyl 1,2,3 triazole; 5 bromo 4 4 methylphenylcarbonyl 1,2,3 triazole; 5 bromo 4 methylcarbonyl 1,2,3 triazole; 5 bromo 4 phenylcarbon

DOI:

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Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-3242809621&partnerID=40&md5=4edf87b425fcce57267655237ffef350
Affiliations	Dept. of Technol. for Organ. Synt., Urals State Technical University, 19, Mira str., 620002 Ekaterinburg, Russian Federation
Author Keywords	α-carbonyl diazoacetonitriles; 5-halo-1,2,3-triazoles; Tandem pseudopericyclic processes
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Correspondence Address	Bakulev, V.A.; Dept. of Technol. for Organ. Synt., Urals State Technical University, 19, Mira str., 620002 Ekaterinburg, Russian Federation
Language of Original Document	English
Abbreviated Source Title	Arkivoc
Source	Scopus