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Cobalt(III)‐Catalyzed Synthesis of Fused Quinazolinones by C–H/N–H Annulation of 2‐Arylquinazolinones with Alkynes
Author(s) -
Kumaran Subramani,
Parthasarathy Kanniyappan
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901763
Subject(s) - metallacycle , chemistry , annulation , alkyne , regioselectivity , catalysis , cobalt , medicinal chemistry , halide , bicyclic molecule , combinatorial chemistry , stereochemistry , organic chemistry , physics , x ray crystallography , diffraction , optics
A convenient and efficient Co III ‐catalyzed cyclization of 2‐arylquinazolinones with alkynes is described. The electron donating as well as withdrawing groups and also halide substituted quinazolinones are compatible with this reaction. This catalytic reaction is highly regioselective with unsymmetrical alkynes. A possible mechanism, involves a formation of five‐membered metallacycle I by metal‐catalyzed aromatic C–H bond activation, alkyne insertion, seven‐membered metallacycle intermediates followed by reductive elimination to give a final product.