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Direct Construction of Diverse Polyheterocycles Bearing Pyrrolidinediones via Rh(III)‐Catalyzed Cascade C−H Activation/Spirocyclization
Author(s) -
Devkota Shreedhar,
Lee HaJin,
Kim Sung Hong,
Lee Yong Rok
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901019
Subject(s) - chemistry , annulation , cascade , catalysis , surface modification , combinatorial chemistry , bearing (navigation) , atom (system on chip) , stereochemistry , medicinal chemistry , organic chemistry , cartography , chromatography , computer science , embedded system , geography
Rh(III)‐catalyzed cascade oxidative annulation of 2‐arylquinazolinones with various maleimides to afford spiroisoindoloquinazolinones bearing pyrrolidinediones is described. Sequential ortho C−H functionalization and spirocyclization via aza‐Michael addition result in the formation of both C−C and C−N bonds in a single operation. This atom‐ and step‐economic strategy provides an efficient and novel approach for the syntheses of diverse polyheterocycles bearing pyrrolidinediones, starting from 2‐heteroarylquinazolinones and 5‐arylpyrazolopyrimidinones, in good to excellent yields.