The representation of charged intermediates in these equations is not to be taken to imply complete ion formation necessarily.

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4-Substituted quinazolines have been selectively converted into mono-Reissert compounds at the 1,2position by use of acid chlorides and trimethylsilyl cyanide. Various reactions of the quinazoline Reissert compounds are reported. For example, conjugate base generation at the 2-position leads to a 1,2rearrangement, whereas substitution occurs in the presence of an alkyl halide, providing, after hydrolysis, 2-alkyl-4-phenylquinazolines in good yield. Ring annellation by intramolecular alkylation is also reported. The quinazoline Reissert compound conjugate base reacts with aldehydes to give alcohol esters which can further be converted, via the alcohol and use of phosgene, to novel oxazolo[4,3a] q u i nazol i ne derivatives.The formation of Reissert compounds of isoquinoline, quinoline and, more recently, phthalazine, has provided entry to a valuable methodology for the exploitation of the chemistry of these ring systems.' Quinazoline is of interest because it has two types of C=N bond for potential functionalisation by the Reissert approach. However, on attempted Reissert compound formation under the usual two-phase conditions with benzoyl chloride and potassium cyanide, ring opening is observed, giving 2'-formylbenzanilide and other product^.^.^The demonstration that trimethylsilyl cyanide could be used as cyanide source in non-aqueous conditions for preparing Reissert compounds of isoquinoline and q ~i n o l i n e , ~ led to examination of its use with quinazoline. It was shown that employment of benzoyl chloride, trimethylsilyl cyanide and quinazoline in a 2: 2: 1 molar ratio with aluminium chloride as catalyst gave the bis-Reissert compound (l), which could be H CN H

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