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A simple procedure for the side-chain lithiation of 2-alkyl-3H-quinazoline-4-thiones: application in synthesis

El-Hiti, Gamal A. 2004. A simple procedure for the side-chain lithiation of 2-alkyl-3H-quinazoline-4-thiones: application in synthesis. Synthesis -Stuttgart- (3) , pp. 363-369. 10.1055/s-2004-815923

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Abstract

Double lithiation of 2-alkyl-3H-quinazoline-4-thiones, at nitrogen and at the a-hydrogen of the 2-alkyl group (Me, Et, nPr), has been achieved with n-butyllithium at -78 0C in anhydrous THF under nitrogen. Reactions of the dilithium reagents obtained with various electrophiles (iodomethane, iodoethane, 1-bromobutane, D2O, benzaldehyde, 4-anisaldehyde, 2-butanone, cyclohexanone, benzophenone, phenyl isothiocyanate, tetraisopropylthiuram disulfide) gave the corresponding modified 2 substituted 3H-quinazoline-4-thiones 4-22 in excellent yields.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: 3H-quinazoline-4-thiones ; lithiation ; organolithiums ; electrophiles
Publisher: Georg Thieme Verlag
ISSN: 0039-7881
Last Modified: 19 Mar 2016 22:25
URI: http://orca-mwe.cf.ac.uk/id/eprint/15606

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