Metal‐Free  N ‐Annulation of 3‐Formylchromones with α‐Amino Ketones for the Construction of Diverse  N ‐Functionalized Pyrroles | Zendy

Shrestha Rajeev | Zendy; Khanal Hari Datta | Zendy; Yang WonGuen | Zendy; Kim Sung Hong | Zendy; Shim JaeJin | Zendy; Lee Yong Rok | Zendy

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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.

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