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Nitrogen bridgehead compounds. Part 88 . Synthesis of 3 H , 7 H ‐[1,4]diazepino[3,4‐ b ]quinazoline‐3,7‐diones
Author(s) -
Szabó Mónika,
Kökösi József,
Örfi László,
Kovács Attila,
Hermecz István
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.5570340104
Subject(s) - chemistry , tricyclic , triethylamine , quinazoline , lactam , stereochemistry , nuclear magnetic resonance spectroscopy , medicinal chemistry , organic chemistry
3 H ,7 H ‐[1,4]Diazepino[3,4‐ b ]quinazolone‐3,7‐diones 9, 11 were synthesized starting from 2‐(1‐bromo‐ethyl)quinazolin‐4(3 H )‐ones 3 and 17 via 2‐[1‐(4‐methoxyphenylamino)ethyl]quinazolin‐4(3 H )‐ones 4 and 18. Cyclization of 3‐[2‐(1‐bromoethyl)‐4‐oxo‐3,4‐dihydroquinazolin‐3‐yl)propionic acid 14 by the action of triethylamine provided the first representative of the tricyclic 7 H ‐[1,4]oxazepino[3,4‐ b ]quinazoline‐3,7‐dione system, compound 15. The new tricyclic derivatives 9, 11 and 15 are characterized by uv, ir and 1 H nmr spectroscopy.