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Updated: Mar 13, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
3-Aryl-2(3)-halogenacrylates as Key Synthons in the Regioselective Synthesis of Two Types of Imidazothiazinotriazines
Sergey S Isakov1, Alexei N Izmest'ev1, Alexander S Steparuk2
1N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., Moscow 119991, Russian Federation.
Abstract:
A method for the synthesis of two series of regioisomeric imidazothiazinotriazines was developed by cyclocondensation of imidazotriazinethiones with 3-aryl-2(3)-halogenacrylates or corresponding acrylonitriles. Regioselectivity of the process depended on the substituents at positions 4a and 7a of imidazotriazinethione. The reaction of 4a,7a-unsubstituted derivatives resulted in imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines of angular structure while the cyclocondensation of 4a,7a-diarylsubstituted compounds led to imidazo[4,5-e][1,3]thiazino[3,2-b][1,2,4]triazines of linear structure. The scope of the method was extended to benzimidazolethione that reacted with 3-aryl-2(3)-halogenacrylates or acrylonitriles to give benzo[4,5]imidazo[2,1-b][1,3]thiazines.
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