2-[(3,5-Diamino-1H-pyrazol-4-yl)methylidene]-1,2-dihydro-3H-indol-3-ones: Synthesis and properties

Abstract

Reactions of 3 acetoxy 2 (2,2 dicyanovinyl)indole with hydrazine hydrate and methyl and phenylhydrazines afforded new indolin 3 one derivatives, namely, 2 [(3,5 diaminopyrazol 4 yl)methylidene]indolin 3 ones. Reactions of the compounds obtained with acetic anhydride and DMF and DMAA dimethyl acetals were studied. Cyclization of 2 [(3,5 diamino 1H pyrazol 4 yl)methylidene] 1,2 dihydro 3H indolinone gave 3 amino 1,5 dihydropyrazolo [4´,3´:5,6]pyrido[3,2 b]indole, a representative of a novel heterocyclic system. Key words: 3 acetoxy 2 (2,2 dicyanovinyl)indole, hydrazines, 2 [(3,5 diamino 1H pyrazol 4 yl)methylidene]indolin 3 ones, acetylation, X ray diffraction analysis, DMF and DMAA dimethyl acetals, cyclization, pyrazolo[4´,3´:5,6]pyrido[3,2 b]indole.

Novel pyrano[3,2-b]indole derivatives: synthesis and some properties

“…3 The goal of the present work was to investigate acid catalyzed transformations of these compounds. Interest in these reactions is due to the re ported 4 transformations of 2 vinylindolin 3 ones in hydro chloric acid into pyrano [3,2 b]indol 2 ones, which can be regarded as heteroanalogs of benzopyran 2 ones.…”