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Reaction of 3-amino-2-alkylquinazolin-4(3H)-ones with several chiral acid chlorides was found to be dependent on the molar proportions. When a 1:1 molar mixture was heated under reflux, the corresponding 3-(diacylamino)- derivatives were obtained in poor yields. However, when a 2:1 molar mixture was reacted in refluxing toluene, the 3-acylamino- derivatives were obtained in good yields based on the acid chloride. Lithiation of the 3-acylamino-2-alkylquinazolin-4(3H)-ones was achieved by the use of LDA in anhydrous THF at -78 °C and the reaction was regioselective at the carbon α to position 2 of the quinazolin- 4(3H)-one moiety. The dilithio reagents thus obtained reacted with electrophiles to give the corresponding 2-substituted deriva- tives in very good yields. The NMR spectra of the products show the expected diastereotopism for all the CH2 groups and provide evidence for long-range asymmetric induction.

Regioselective Lithiation of Chiral 3-Acylamino-2-alkylquinazolin-4(3H)-ones: Application in Synthesis