Smith, Keith  ORCID: https://orcid.org/0000-0003-4838-5651, 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: | 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: | 05 Aug 2026 04:40 |
| URI: | https://orca.cardiff.ac.uk/id/eprint/12713 |
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