A Simple Procedure for the Side-Chain Substitution of 2-Alkyl-3H-quinazo­line-4-thiones: Application in Synthesis

Gamal A. El-Hiti

doi:10.1055/s-2004-815923

PAPER

A Simple Procedure for the Side-Chain Substitution of 2-Alkyl-3H-quinazoline-4-thiones: Application in Synthesis

Gamal A. El-Hiti*
Centre for Clean Chemistry, Department of Chemistry, University of Wales Swansea, Singleton Park, Swansea SA2 8PP, UK
Fax: +44(1792)295747; e-Mail: g.a.el-hiti@swansea.ac.uk;

Abstract

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Abstract

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

Key words

3H-quinazoline-4-thiones - lithiation - organolithiums - electrophiles

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References

Permanent address: El-Hiti G. A.; Department of Chemistry, Faculty of Science, Tanta University, Tanta 31527, Egypt.

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A Simple Procedure for the Side-Chain Substitution of 2-Alkyl-3H-quinazo­line-4-thiones: Application in Synthesis

A Simple Procedure for the Side-Chain Substitution of 2-Alkyl-3H-quinazoline-4-thiones: Application in Synthesis