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Synthesis of 1,2,4-triazolo[5′,1′:2,3][1,3]thiazino[6,5-b]indol-10(5H)-ones based on 2-chloro-1H-indole-3-carbaldehyde

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Abstract As a result of the reaction of 2-chloro-1H-indole-3-carbaldehydes with 4-amino-5-alkyl-4H-1,2,4-triazole-3-thiols in DMF, representatives of a new heterocyclic system, 1,2,4-triazolo[5′,1′:2,3][1,3]thiazino[6,5-b]indol-10(5H)-one, were obtained. The reaction proceeds unusually, with a the release… Click to show full abstract

Abstract As a result of the reaction of 2-chloro-1H-indole-3-carbaldehydes with 4-amino-5-alkyl-4H-1,2,4-triazole-3-thiols in DMF, representatives of a new heterocyclic system, 1,2,4-triazolo[5′,1′:2,3][1,3]thiazino[6,5-b]indol-10(5H)-one, were obtained. The reaction proceeds unusually, with a the release of an ammonia molecule. The structure of 1,2,4-triazolo[5′,1′:2,3][1,3]thiazino[6,5-b]indol-10(5H)-ones was established by X-ray diffraction. The obtained compounds contain rutalexin scaffold in the structure and are promising in terms of biological activity.

Keywords: thiazino indol; chloro indole; triazolo thiazino; indol ones

Journal Title: Tetrahedron Letters
Year Published: 2020

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