Premium
A Tandem Strategy for the Synthesis of 1 H ‐Benzo[ g ]indazoles and Naphtho[2,1‐ d ]isoxazoles from o ‐Alkynylarene Chalcones
Author(s) -
Akbar Sikkandarkani,
Srinivasan Kannupal
Publication year - 2013
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.201201576
Subject(s) - chemistry , quinoline , tandem , hydroxylamine , electrophile , iodine , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis , materials science , composite material
o ‐Alkynylarene chalcones when treated with hydrazines and hydroxylamine in the presence of iodine gave 1 H ‐benzo[ g ]indazoles and naphtho[2,1‐ d ]isoxazoles, respectively. The transformations involve tandem oxidative cyclocondensation/electrophilic hydroarylation. The methodology was applied to quinoline‐based chalcones, which also afforded the corresponding quinoline‐fused benzindazole and benzisoxazole.