Functionalization of 2-methyl-3-o-tolyl-4 (3H)-quinazolinone and related compounds through carbanion reactions at the 2-methyl group

TL Rathman, MC Sleevi, ME Krafft…

Index: Rathman, Terry L.; Sleevi, Mark C.; Krafft, Marie E.; Wolfe, James F. Journal of Organic Chemistry, 1980 , vol. 45, # 11 p. 2169 - 2176

Full Text: HTML

Citation Number: 25

Abstract

2-Methyl-3-o-tolyl-4 (3H)-quinazolinone (methaqualone, 3a), 2, 3-dimethyl-4 (3H)- quinazolinone (3b), and 2-methyl-3-phenyl-4 (3H))-quinazolinone (3c) were converted to the 2-lithiomethyl derivatives 4a, 4b, and 4c, respectively, by means of lithium diisopropylamide in THF-hexane at 0" C. Reactions of 4a-c with a series of electrophilic reagents led to elaboration at the original 2-methyl group. Thus, 4a was alkylated with methyl iodide, allyl ...