2-substituted quinazolines, amidine synthesis

Acetates 5 with an acyl group at position 6 react with amidines, guanidine, C9-alkylisoureas, and 5-alkylisothioureas, respectively, in ethanol to give quinazolin-5-ols 6 in good yields. The synthesis is successful only with 2- and 4-substituted acetates and is especially useful for the preparation of 2-methoxy-, 2-(methylsulfanyl)-, and 2-aminoquinazolin-5-ols." ... 

On the other hand, nitriles are widely used as intermediates in the synthesis of many types of heterocycles [7] and other compounds of interest in medicinal chemistry, for example, 3,4-dihydroisoquinolines [8], imidazoles [9], indoles [10], lactim ethers [11], napthyridines [12], pyridones [13], pyridopyrimidi-nes [14], pyrimidines [15], quinazolines [16], quinazolones [17], quinolines [18], sydnones [19], 1,2,4,5-tetrazines [20], tetrazoles [21,22], 1,2,4-triazoles [20], N-substituted amides [23], amidines [24] and basic esters [25]. 

Scheme 60 Synthesis of 2-substituted quinazolinones and quinazolines via Cul-catalyzed N-arylation of amidines...

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