3-Aryl-2(3)-halogenacrylates as Key Synthons in the Regioselective Synthesis of Two Types of Imidazothiazinotriazines

3-Aryl-2(3)-halogenacrylates as Key Synthons in the Regioselective Synthesis of Two Types of Imidazothiazinotriazines Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2026, Volume: 91, Number: 12, Pages: 4422-4432 Pages count : 11 DOI: 10.1021/acs.joc.6c00071

Authors

Isakov Sergey S. ¹ , Izmest’ev Alexei N. ¹ , Steparuk Alexander S. ² , Irgashev Roman A. ² , Gazieva Galina A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., Moscow 119991, Russian Federation
2	I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 S. Kovalevskoy Str., Ekaterinburg 620137, Russian Federation

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,7adiarylsubstituted 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.

Isakov S.S. , Izmest’ev A.N. , Steparuk A.S. , Irgashev R.A. , Gazieva G.A.
3-Aryl-2(3)-halogenacrylates as Key Synthons in the Regioselective Synthesis of Two Types of Imidazothiazinotriazines
Journal of Organic Chemistry. 2026. V.91. N12. P.4422-4432. DOI: 10.1021/acs.joc.6c00071 WOS Scopus OpenAlex

Submitted:	Jan 12, 2026
Accepted:	Mar 10, 2026
Published online:	Mar 12, 2026

≡ Web of science:	WOS:001713234500001
≡ Scopus:	2-s2.0-105034113765
≡ OpenAlex:	W7135061611