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Synthesis, alkylation and ring opening of two differently fused pyridoquinazolones
Author(s) -
Timári Géza,
Hajós György,
Messmer András
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270730
Subject(s) - chemistry , alkylation , reagent , alkyl , moiety , ring (chemistry) , nucleophile , pyridine , salt (chemistry) , pyrimidine , medicinal chemistry , stereochemistry , organic chemistry , catalysis
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.