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16.13.4.4.3 Methyl Group Modification

DOI: 10.1055/sos-SD-016-00745

Kikelj, D.Science of Synthesis, (200416725.

The 2-methyl and 4-methyl groups of quinazolines behave like active methylene groups and react with electrophilic reagents in the presence of a base, forming exocyclic CC bonds.[‌5‌,‌985‌,‌986‌] Thus, butyllithium converts 2-alkylquinazolin-4(3H)-ones 330 into dianions 331 which react with a variety electrophiles, e.g. alkyl halides, deuterium oxide, phenyl isocyanate, and aromatic aldehydes and ketones, to give the corresponding 2-substituted derivatives 332, generally in very good yields (Scheme 247).[‌987‌,‌988‌]

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References


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