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. Issue 45 (5th November 2020)

• Record Type: Journal Article
• Authors: Vikrishchuk, Natalia I.; Tkachev, Valerii V.; Borodkin, Gennady S.; Gazieva, Galina A.; Shilov, Gennady V.
• Is Part Of: Tetrahedron letters. Volume 61:Issue 45(2020)
• Publication Date: 2020-11-05
• Subjects: Indole -- NN bond cleavage -- Rearrangement -- Triazolothiazino[6, 5-b]indol-10(5H)-one; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.152490
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Representatives of a new heterocyclic system obtained. A previously undescribed reaction of amines with aldehydes with the elimination of the amino group. Simple and effective synthesis pharmacologically oriented compounds. 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.