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Nitrogen bridgehead compounds. Part 85 . Synthesis and reactivity of 3,4‐dihydro‐1 H ,6 H [1,4]oxazino[3,4‐ b ]quinazolin‐6‐ones
Author(s) -
Hermecz István,
Szilágyi Ildikó,
Orfi László,
Kökösi József,
Szász György
Publication year - 1993
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.5570300539
Subject(s) - chemistry , reagent , reactivity (psychology) , methylene , yield (engineering) , bromine , nitrogen , medicinal chemistry , chloride , nitrous acid , stereochemistry , organic chemistry , medicine , materials science , alternative medicine , pathology , metallurgy
3,4‐Dihydro‐1 H ,6 H ‐[1,4]oxazino[3,4‐ b ]quinazolin‐6‐one 3 and its 1‐methyl and 1‐hydroxy derivatives 8 and 13 were prepared by different routes. The active methylene group of compound 3 was reacted with electro‐hilic reagents (bromine, phenyldiazonium chloride, nitrous acid, a Vielsmeier‐Haack reagent, aromatic aldehydes and diethyl oxalate) to yield 1‐substituted‐3,4‐dihydro[1 H ,6 H )‐1,4‐oxazino[3,4‐ b ]quinazo‐lin‐6‐ones. The reactivity of 1‐hydroxy and 1‐bromo derivatives 13 and 15 were also investigated in some reactions. The 3,4‐dihydro‐l H ,6 H ‐[1,4]oxazino[3,4‐ b ]quinazolin‐6‐ones were characterized by means of uv, 1 H and 13 C nmr spectroscopy.