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Metal‐Free N‐Annulation of 3‐Formylchromones with α‐Amino Ketones for the Construction of Diverse N‐Functionalized Pyrroles
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-05-07 , DOI: 10.1002/ajoc.202000151
Rajeev Shrestha 1 , Hari Datta Khanal 1 , Won‐Guen Yang 2 , Sung Hong Kim 2 , Jae‐Jin Shim 1 , Yong Rok Lee 1
Affiliation  

A novel and efficient one‐pot approach for the synthesis of diverse and polyfunctionalized pyrroles by the mild organic base‐promoted N‐annulation of 3‐formylchromones with N‐(2‐oxo‐2‐arylethyl)sulfonamides, N‐(2‐oxo‐2‐phenylethyl)methanesulfonamide, or 1‐phenyl‐2‐(phenylamino)ethan‐1‐ones is described. The reaction proceeds via cascade Knoevenagel condensation/intramolecular Michael addition/ring opening. This protocol provides rapid access to biologically interesting polysubstituted pyrroles bearing N‐arylsulfonyl/N‐methylsulfonyl/N‐aryl moieties or a free N−H group.

中文翻译:

带有α-氨基酮的3-甲酰基色酮的无金属N环构反应,用于构建各种N功能化的吡咯

一种新颖而有效的一锅法,通过与N-(2-氧代-2-芳基乙基)磺酰胺,N-(2-氧代)的3-甲酰基色酮的温和的有机碱促进的N-环化合成多种多样的多官能吡咯描述了2-苯基乙基)甲磺酰胺或1-苯基-2-(苯基氨基)乙-1-酮。反应通过级联Knoevenagel缩合/分子内迈克尔加成/开环进行。这个协议提供了生物学意义的多取代的吡咯轴承快速访问Ñ -arylsulfonyl / Ñ甲基磺酰基/ ñ -芳基部分或无N-H基团。
更新日期:2020-07-08
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