期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2012, 期 18, 页码 3492-3499出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200276
关键词
Nitrogen heterocycles; Fused-ring systems; Synthetic methods; Copper
资金
- Council of Scientific and Industrial Research (CSIR), New Delhi
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.
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