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A simple and convenient procedure for lithiation and side-chain substitution of 2-alkyl-4-(methylthio)quinazolines and 2-alkyl-4-methoxyquinazolines

Smith, Keith, El-Hiti, Gamal A. and Hegazy, Amany Saber 2005. A simple and convenient procedure for lithiation and side-chain substitution of 2-alkyl-4-(methylthio)quinazolines and 2-alkyl-4-methoxyquinazolines. Synthesis (Stuttgart) (17) , pp. 2951-2961. 10.1055/s-2005-916036

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Abstract

2-Methyl-4-(methylthio)quinazoline has been lithiated, in the 2-methyl group, with n-BuLi at -78 °C in THF. The lithium reagent thus obtained reacts with a variety of electrophiles (iodomethane, iodoethane, D2O, benzaldehyde, 4-anisaldehyde, hexan-2-one, acetophenone, benzophenone, cyclohexanone) to give modified 2-substituted 4-(methylthio)quinazolines in excellent yields. Similarly, lithiation of 4-methoxy-2-methylquinazoline followed by reactions with various electrophiles gave the corresponding modified 2-substituted 4-methoxyquinazolines in excellent yields. Lithiations of 2-ethyl-4-(methylthio)quinazoline, 4-(methylthio)-2-propylquinazoline, 2-ethyl-4-methoxyquinazoline and 4-methoxy-2-propylquinazoline, followed by reactions with a range of electrophiles, behave in a similar manner to give the corresponding modified 2-substituted derivatives in good yields.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: lithiation ; side-chain ; substitution ; 2-alkyl-4-(methylthio)quinazoline ; 2-alkyl-4-methoxyquinazoline ; electrophiles
Publisher: Georg Thieme Verlag
ISSN: 0039-7881
Date of First Compliant Deposit: 30 March 2016
Last Modified: 04 Jun 2017 02:51
URI: http://orca.cf.ac.uk/id/eprint/12713

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