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1,4‐Benzoxazin‐2‐ones, benzo[ d ]oxazoles and 2 H ‐1,4‐benzoxazines from the reaction of 2‐(methoxyimino)benzen‐1‐ones with arylacetates, arylacetic acids and trans‐ stilbene
Author(s) -
Nicolaides Demetrios N.,
Awad R. Wajih,
Varella Evangelia A.
Publication year - 1996
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.5570330318
Subject(s) - chemistry , yield (engineering) , stereochemistry , medicinal chemistry , phenanthrene , reaction conditions , catalysis , organic chemistry , materials science , metallurgy
10‐(Methoxyimino)phenanthrene‐9‐one 1 reacts thermally with the arylacetic derivatives 2(a‐j ) to yield the corresponding 1,4‐benzoxazin‐2‐ones 4(a‐d,f ) and benzo[ d ]oxazoles 5(a‐e,g ). Similarly, reaction of the monoximes 7a, 7b with compounds 2a, 2d respectively affords 8a, 8b , while action of trans ‐stilbene on the monoximes 1, 7a, 7b leads to the 1,4‐benzoxazines 10, 11, 13 , obtained along with the corresponding 2‐phenyloxazoles 5a, 8a, 8c and compound 12 .