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Synthesis of 5,6‐dimethoxyquinazolin‐2(1 H )‐ones
Author(s) -
Press Jeffery B.,
Bandurco Victor T.,
Wong Elizabeth M.,
Hajos Zoltan G.,
Kanojia Ramesh M.,
Mallory Robert A.,
Deegan Edward G.,
Mcnally James J.,
Roberts Jerry R.,
Cotter Mary Lou,
Graden David W.,
Lloyd John R.
Publication year - 1986
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.5570230643
Subject(s) - chemistry , substituent , dimer , vanillin , solid state , stereochemistry , combinatorial chemistry , organic chemistry
Synthesis of 5,6‐dimethoxyquinazolin‐2(1 H )‐one derivatives was the subject of investigations leading to the preparation of title compounds 11, 13, 14 and 26 . Target quinazolines 1 were synthesized in three ways; the route starting from o ‐vanillin via the intermediacy of 6‐amino‐2,3‐dimethoxyacetophenone ( 19 ) was used for most of the preparative work. The unexpected formation of an acid‐labile dimer of 13 was discovered and solid state 13 C nmr was used for structural assignment. The 5‐methoxy substituent in these systems shows anomalous spectral characteristics and, in one case, was cleaved in acid media to 22 .