Three-component synthesis of polysubstituted 6-azaindolines and its tricyclic derivatives.
[Reaction: see text] By simply heating a toluene solution of isocyanoacetamide (3), amine (4), and aldehyde (5), a clean three-component reaction occurred to provide the pyrrolidinone-fused azaindoline (2). In this multicomponent reaction, the isocyanoacetamide (3) reacted four times in a highly ordered manner creating three heterocylic rings with the concurrent formation of five chemical bonds and a minimal loss of molecular weight. Heating is the only external energy required to promote this powerful complexity-generating MCR.
Fayol
Aude
A
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette, France.
Zhu
Jieping
J
D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D001372:Aza Compounds; D006575:Heterocyclic Compounds, 3-Ring; D007211:Indoles