Electron deficient heteroaromatic ammonioamidates. Part 24. N-(Quinazolin-3-io)amidates. Part 11. The photochemistry of N-(6,7-methylenedioxyquinazolin-3-io)amidates in acetone

Abstract

N-(Quinazolin-3-io)amidates (1) may exist, depending on the nature of the groups R, R¹, and R², and in the absence of nucleophiles, as equilibrium mixtures of the monomeric (1) and dimeric (3) forms. For the first time evidence has been found for the generation of photoproducts of the dimeric forms (3)via irradiation of the quinazolinioamidates (1a–c) in acetone in which substantial amounts of the dimers (3a–c) are present. Thus, the quinazolinioamidates (1) are the only heteroaromatic ammonioamidates which are known not only to exist in three forms, viz. the monomer, the adducts (2), and the dimers (3), but also to furnish characteristic photoproducts of all three forms.