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Addition of alkyllithiums to 3H-quinazoline-4-thione and various substituted quinazoline derivatives; application in synthesis

Smith, Keith, El-Hiti, Gamal A. and Hegazy, Amany Saber 2005. Addition of alkyllithiums to 3H-quinazoline-4-thione and various substituted quinazoline derivatives; application in synthesis. Journal of Sulfur Chemistry 26 (2) , pp. 121-129. 10.1080/17415990500151472

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Abstract

Reaction of 3H-quinazoline-4-thione (1) with two mole equivalents of an alkyllithium (t-BuLi, n-BuLi or MeLi) at−78 °C in dry THF gave the corresponding 2-alkyl-1,2-dihydro-3H-quinazoline-4-thione (4, 5 or 6) in high yield. Similarly, reactions of 4-(methylthio)quinazoline (7), 4-(ethylthio)quinazoline (8) and 4-methoxyquinazoline (9) with alkyllithiums (one mole equivalent) gave the corresponding 4-substitued 2-alkyl-1,2-dihydroquinazolines 11–18. On the other hand, blocking position 2 with a phenyl group in 4-(methylthio)-2-phenylquinazoline (20) and 4-methoxy-2-phenylquinazoline (21) resulted in reaction with two mole equivalents of alkyllithiums to give 4,4-dialkyl-2-phenyl-3,4-dihydroquinazolines 22–24.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Biosciences
Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: 3H-Quinazoline-4-thione, 4-(Alkylthio)quinazoline, Synthesis, Alkyllithiums, Nucleo-philic addition
Publisher: Taylor and Francis
ISSN: 1741-5993
Date of First Compliant Deposit: 30 March 2016
Last Modified: 04 Jun 2017 02:56
URI: http://orca.cf.ac.uk/id/eprint/14209

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