Tuning of the imidazotriazinethione structures for the regio-divergent synthesis of isomeric imidazothiazolotriazines

Tuning of the imidazotriazinethione structures for the regio-divergent synthesis of isomeric imidazothiazolotriazines Full article

Journal

Synthetic Communications
ISSN: 1532-2432 , E-ISSN: 0039-7911

Output data

Year: 2026, DOI: 10.1080/00397911.2026.2679592

Authors

Izmest’ev Alexei N. ¹ , Kolotyrkina Natalya G. ¹ , Kravchenko Angelina N. ¹ , Gazieva Galina A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Two series of isomeric functionalized derivatives of imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine (linear isomer) and imidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine (angular isomer) were synthesized via regiodivergent condensation of imidazo[4,5-e]-1,2,4-triazin-3-thiones with acetylene dicarboxylic acid dimethyl and diethyl esters. The direction of condensation depended on aryl substituent position in starting imidazotriazinethione. 7-Alkyl-5-aryl-substituted imidazotriazinethiones reacted with dialkyl acetylenedicarboxylates to afford predominantly linear isomers. In contrast, the reaction of 5-alkyl-7-arylimidazotriazinethiones with dialkyl acetylenedicarboxylates resulted in angularar imidazothiazolotriazines. Previously, similar angular isomers were obtained only by base-catalyzed amidine rearrangement of the linear imidazothiazolotriazines.

Izmest’ev A.N. , Kolotyrkina N.G. , Kravchenko A.N. , Gazieva G.A.
Tuning of the imidazotriazinethione structures for the regio-divergent synthesis of isomeric imidazothiazolotriazines
Synthetic Communications. 2026. DOI: 10.1080/00397911.2026.2679592 OpenAlex

Submitted:	Mar 9, 2026
Published print:	May 30, 2026

≡ OpenAlex:

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