Synthesis, alkylation and ring opening of two differently fused pyridoquinazolones

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Abstract
Alkylation of two differently (linearly and angularly) fused pyridoquinazolones 7 and 10 have been investigated. The linear 7 afforded exclusively N‐alkyl derivatives 4, whereas the angular 10 gave both N‐ and O‐alkyl products 5 and 11, respectively depending on the type of the reagent used. Reaction of the new alkylated salts 4, 5, and 11 with nucleophiles was found strongly dependent on the fusion type of the substrates: the reaction of the linear salt 4 led to opening of the pyrimidine moiety, and the angularly fused salts 5, 11 reacted at the pyridine site to give quinazolyldieneamines 17, 19. Regioselectivities of the observed conversions were interpreted on FMO basis.