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A short and unequivocal synthesis of 5‐aminotetrazolo[1,5‐ a ]‐quinazoline as a tricyclic analogue of 4‐(3‐bromoanilino)‐6,7‐dimethoxyquinazoline (PD 153035)
Author(s) -
Bencteux Edith,
Houssin Raymond
Publication year - 1997
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.5570340447
Subject(s) - tricyclic , quinazoline , chemistry , cycloaddition , stereochemistry , derivative (finance) , ring (chemistry) , combinatorial chemistry , organic chemistry , financial economics , economics , catalysis
The discovery of 4‐(3‐bromoanilino)‐6,7‐dimethoxyquinazoline (PD 153035) as an extremely potent inhibitor of the tyrosine kinase activity of the epidermal growth factor receptor led to the preparation of several fused tricyclic quinazoline analogues. The present paper reports a new tricyclic derivative: 5‐(3‐bromoanilino)‐7,8‐dimethoxytetrazolo[1,5‐ a ]quinazoline. This compound was synthesized by two different pathways via a 1,3‐dipolar cycloaddition of an azide at carbon 2 of the quinazoline ring.