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Note | Regular issue | Vol 57, No. 2, 2002, pp.323-326
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9386
Preparation of a Useful Synthetic Precursor, 2-Substituted 4(3H)-Quinazolinone: Directed Lithiation and N3-Deprotection of 3-t-Butoxycarbonyl-4(3H)-quinazolinone

Osamu Sugimoto,* Yasuhiro Yamauchi, and Ken-ichi Tanji*

*Laboratory of Organic Chemistry, School of Food and Nutritional Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan

Abstract

Directed lithiation of 3-t-butoxycarbonyl-4(3H)-quinazolinone using LDA was accomplished to afford 2-substituted 3-t-butoxycarbonyl-4(3H)-quinazolinones. The t-butoxycarbonyl group of these products was easily deprotected to give key intermediates for the synthesis of quinazoline derivatives, 2-substituted 4(3H)-quinazolinones, in good yield.