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Metal‐Free N ‐Annulation of 3‐Formylchromones with α‐Amino Ketones for the Construction of Diverse N ‐Functionalized Pyrroles
Author(s) -
Shrestha Rajeev,
Khanal Hari Datta,
Yang WonGuen,
Kim Sung Hong,
Shim JaeJin,
Lee Yong Rok
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000151
Subject(s) - chemistry , annulation , intramolecular force , knoevenagel condensation , michael reaction , ring (chemistry) , pyrrole , medicinal chemistry , combinatorial chemistry , aryl , stereochemistry , organic chemistry , catalysis , alkyl
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.