Premium
SeO 2 Mediated Synthesis of Selected Heterocycles by Oxidative C−C Bond Cleavage of AcetophenoneDerivatives
Author(s) -
Khan Danish,
Ahmed Naseem,
Alsharif Meshari A.,
Alahmdi Mohammed Issa,
Mukhtar Sayeed
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.201901216
Subject(s) - benzoxazole , benzothiazole , chemistry , bond cleavage , aniline , benzimidazole , aryl , acetophenone , quinazolinone , cleavage (geology) , alkyl , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
An interestingcyclization reactions of aryl ketones with 2‐amino aniline derivatives under SeO 2 (oxidant) are described for the synthesis of benzoxazole, benzothiazole, benzimidazole and quinazolinone through the C−C cleavage of acetophenone. The reaction likely involves sequential C−N, C−O and C−S bond formation followed by C(CO)−C(alkyl) bond cleavage. Various substituted fused heterocycles are obtained in good to excellent (gram scale) yields in a single step from readily available acetophenones.