30362-08-4Relevant academic research and scientific papers
One-step synthesis of 2-amino-5h-pyrimido[5,4-b]indoles, substituted 2-(1,3,5-triazin-2-yl)-1h-indoles, and 1,3,5-triazines from aldehydes
Biswas, Subhasish,Batra, Sanjay
scheme or table, p. 3492 - 3499 (2012/08/13)
An efficient one-step synthesis of 2-amino-5H-pyrimido[5,4-b]indoles through a copper-catalyzed cascade reaction between 3-haloindole-2-carbaldehydes and guanidine hydrochloride is described. In contrast, the base-mediated reactions of either 3-haloindole-2-carbaldehydes or substituted indole-2-carbaldehydes with substituted amidine hydrochlorides in DMSO result in the formation of 2-(1,3,5-triazin-2-yl)-1H-indole derivatives in one step in excellent yields. Studies toward exploring the utility of the method demonstrate that even substituted benzaldehydes undergo a similar reaction to efficiently yield 2,4,6-trisubstituted 1,3,5-triazines. A plausible mechanism for the formation of substituted 1,3,5-triazines identifies the role of DMSO as an oxidant during the reaction. The synthesis of 2-amino-5H-pyrimido[5,4-b]indoles from 3-haloindole-2-carbaldehyde and guanidine hydrochloride is described. In contrast, 3-haloindole-2-carbaldehydes or indole-2-carbaldehydes react with substituted amidine hydrochlorides to give 2-(1,3,5-triazin-2-yl)-1H-indole derivatives in excellent yields. The latter protocol was used to prepare 2,4,6-trisubstituted 1,3,5-triazines.
Synthesis of s-Triazines Bearing Three Different Substituents (1)
Lin, Yang-i,Fields, Thomas L.,Lee, Ving J.,Lang, S. A.
, p. 613 - 615 (2007/10/02)
Reaction of N'-acyl-N,N-dimethylamidines with hydrogen sulfide in acetic acid gave N-thioacylbenzamides in almost quantitative yields.S-Ethylation of the N-thioacylbenzamides with iodoethane gave N-aroylthioimidates in excellent yields.Reaction of the N-a
