Construction of New Heterocyclic System, Imidazo[4,5‐d]thiazolo[4,3‐b]oxazole, via Cascade Reaction of Thioglycolurils with α‐Bromoketones

Construction of New Heterocyclic System, Imidazo[4,5‐d]thiazolo[4,3‐b]oxazole, via Cascade Reaction of Thioglycolurils with α‐Bromoketones Full article

Journal

Asian Journal of Organic Chemistry
ISSN: 2193-5815 , E-ISSN: 2193-5807

Output data

Year: 2024, Volume: 13, Number: 11, Article number : e202400369, Pages count : DOI: 10.1002/ajoc.202400369

Authors

Vinogradova Ekaterina ¹ , Karnoukhova Valentina ² , Kravchenko Angelina N. ¹ , Gazieva Galina A. ¹

Affiliations

1	Russian Academy of Sciences, N.D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect, 47,, Moscow, RUSSIAN FEDERATION
2	FSBSI A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Not provided, Moskva, RUSSIAN FEDERATION

A method for the synthesis of new heterocyclic system representatives, i. e. imidazo[4,5-d]thiazolo[4,3-b]oxazole derivatives, by the reaction of thioglycolurils with α-bromoketones has been developed. The reaction includes a cascade one-pot S-alkylation/nucleophilic addition/ring-opening/ring-closing process. This protocol is compatible with a broad scope of α-bromoketones, diastereoselectively affording diverse products with 3aS*,4aR*,8aR*-imidazo[4,5-d]thiazolo[4,3-b]oxazole core in 40–76 % yields.

Vinogradova E. , Karnoukhova V. , Kravchenko A.N. , Gazieva G.A.
Construction of New Heterocyclic System, Imidazo[4,5‐d]thiazolo[4,3‐b]oxazole, via Cascade Reaction of Thioglycolurils with α‐Bromoketones
Asian Journal of Organic Chemistry. 2024. V.13. N11. e202400369 . DOI: 10.1002/ajoc.202400369 WOS Scopus OpenAlex

≡ Web of science:	WOS:001319949300001
≡ Scopus:	2-s2.0-85204772285
≡ OpenAlex:	W4401427577