Abstract
1-Aryl-3-[2-(ethoxycarbonyl)benzothien-3-yl]carbodiimides 4 , obtained from aza-Wittig reactions of iminophosphorane 3 with aryl isocyanates, reacted with secondary amines, phenols, or alkanols in the
presence of a catalytic amount of potassium carbonate or sodium alkoxide to give 2-substituted
benzothieno[3,2-d ]pyrimidin-4(3H )-ones 6 in good yields. The reaction of carbodiimides 4 with primary amines RNH2 (R ≠ H, Me) in the presence of sodium ethoxide selectively produced one regioisomer
8 via a base-catalyzed cyclization mechanism. However, a different regioisomer 9 was obtained when primary amines RNH2 (R = H, Me) were used in the absence of sodium ethoxide via a direct cyclization
mechanism.
Key words
benzothieno[3,2-d ]pyrimidin-4(3H )-one - iminophosphorane - carbodiimide - aza-Wittig reaction - synthesis
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