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An Expedient Lewis‐Acid‐Catalyzed Microwave‐Assisted Domino Approach to Coumarin‐Fused Pyrroles and Related Heterocycles under Neat Conditions
Author(s) -
Yadav Anubha,
Gudimella Santosh K.,
Samanta Sampak
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201903711
Subject(s) - annulation , chemistry , lewis acids and bases , pyrrole , lewis acid catalysis , catalysis , coumarin , enamine , domino , combinatorial chemistry , organic chemistry , electrophile
A superior Lewis acid‐catalyzed and microwave‐assisted, facile, solvent‐free, one‐pot quick access to a novel class of a set of diversely substituted coumarin, dimedone and naphthoquinone‐fused pyrroles via an annulation reaction between different kinds of carbo‐and heterocyclic enaminones and a group of α‐aroyl/heteroaryl/acetylidene malonates, 3‐aroylidene‐2‐oxindoles is reported. This LUMO‐lowering technique involving a powerful Lewis acid relies on the installation of pyrrole rings good to high chemical yields with a wide scope of diversely substituted substances. Furthermore, a direct C(sp 3 )‐H hydroxylation of 3‐pyrrolocoumarinyl‐2‐oxindoles to therapeutically exciting 3‐hydroxy‐3‐pyrrolocoumarinyl‐2‐oxindoles bearing a tetra‐substituted chiral carbon center in high yields was achieved under metal‐free conditions.