Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines

Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines Full article

Journal

Beilstein Journal of Organic Chemistry
ISSN: 2195-951X , E-ISSN: 1860-5397

Output data

Year: 2023, Volume: 19, Pages: 1047-1054 Pages count : 8 DOI: 10.3762/bjoc.19.80

Authors

Vinogradov Dmitry B ¹ , Izmest'ev Alexei N ¹ , Kravchenko Angelina N ¹ , Strelenko Yuri A ¹ , Gazieva Galina A ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., Moscow 119991, Russian Federation.

A series of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines was synthesized via a cascade sequence of hydrolysis and skeletal rearrangement of imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazin-7(8H)-ylidene)acetic acid esters in methanol upon treatment with excess KOH. Imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazin-6(7H)-ylidene)acetic acid esters are also suitable substrates for the reaction. In this case hydrolysis and thiazole ring expansion were accompanied with the change of the thiazolotriazine junction type from thiazolo[3,2-b][1,2,4]triazine to thiazino[2,3-c][1,2,4]triazine.

Vinogradov D.B. , Izmest'ev A.N. , Kravchenko A.N. , Strelenko Y.A. , Gazieva G.A.
Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines
Beilstein Journal of Organic Chemistry. 2023. V.19. P.1047-1054. DOI: 10.3762/bjoc.19.80 WOS Scopus OpenAlex

≡ Web of science:	WOS:001042834300001
≡ Scopus:	2-s2.0-85168717525
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