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Quinazolines. XI. Synthesis of 2,4‐diamino‐5, 10‐diliydrobenzo[g] quinazolines
Author(s) -
Rosowsky Andre,
Burrows Elizabeth P.,
Huang Ping C.,
Modest Edward J.
Publication year - 1972
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.5570090609
Subject(s) - chemistry , guanidine , amination , alkylation , condensation , liquid ammonia , organic chemistry , amidine , ammonia , medicinal chemistry , catalysis , physics , thermodynamics
An unequivocal synthesis of 2,4‐diamino‐5,10‐dihydrobenzo[ g ]quinazolines is described, starting from methyl 2‐tetralone‐3‐carboxylates. Condensation with guanidine yielded 2‐amino‐4‐hydroxy derivatives, which were thiated with phosphorus pentasulfide and S ‐alkylated with dimethyl sulfate. The resultant 2‐amino‐4‐methylthio compounds were converted into 2,4‐diamino derivatives by amination at elevated temperature and pressure. Attempted synthesis from 3‐cyano‐1,4‐dihydro‐2‐methoxynaphthalene and guanidine was unsuccessful.