A versatile domino process for the synthesis of substituted 3-aminomethylene-chromanones and 2-pyridones catalyzed by CsF

作者：Pintiala Catalin; Lawson Ata Martin^*; Comesse Sebastien; Daich Adam

来源：Tetrahedron Letters, 2013, 54(22): 2853-2857.

DOI：10.1016/j.tetlet.2013.03.096

• 2-Pyridone
• Domino process
• Catalytic process
• 3-Aminomethylene-chromanone
• alpha,beta-Unsaturated chromone

The addition of various primary amines onto 3-alpha,beta-unsaturated diester chromone derivative was studied under mild conditions. Basically, this reaction provided 2-pyridone-based compounds through an interesting domino 'Addition/Ring Opening/Ring Closure' process (ARORC). In this study, aniline and tryptamine series exhibited different reactivity profiles leading unexpectedly to 3-aminomethylene chromanones with or without the 2-pyridone derivatives. This constitutes the first description and study of 3-aminomethylene chromanone formation that is supposed to follow a domino process combining 'Addition/Ring Opening/Ring Closure by Oxa-Michael addition' (ARORCOM).

• 出版日期2013-5-29