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Tandem Oxidative Cyclocondensation towards 2,3‐Disubstituted Quinazolinones in the Presence of [Bmim][BF 4 ] and Iodine
Author(s) -
Sofi Firdoos Ahmad,
Sharma Rohit,
Chakraborti Asit K.,
Bharatam Prasad V.
Publication year - 2019
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.201900969
Subject(s) - chemistry , tandem , ionic liquid , iodine , oxidative phosphorylation , aryl , quenching (fluorescence) , cascade reaction , combinatorial chemistry , organic chemistry , medicinal chemistry , catalysis , fluorescence , biochemistry , materials science , alkyl , physics , quantum mechanics , composite material
The metal‐free synthesis of 2‐aryl‐3‐arylmethylquinazolin‐4(3H)‐one is achieved through ionic liquid mediated and I 2 ‐promoted tandem oxidative cyclocondensation of isatoic anhydrides with arylmethylamines as the common precursor for the 2‐aryl and 3‐arylmethyl moieties. Radical quenching experiments suggest a non‐radical mechanistic pathway and the operation under anaerobic condition confirms the essential role of I 2 as the oxidant. Metal‐free synthesis, reduced reaction times to afford higher product yields, recyclability of the IL used as the reaction medium, and the feasibility of gram scale operation are some advantages.