REACTIONS OF O-METHYL O-QUINONE MONOOXIMES WITH METHYL-SUBSTITUTED, METHYLENE-SUBSTITUTED AND METHINE-SUBSTITUTED AROMATIC-COMPOUNDS - SYNTHESIS OF BENZO[D]OXAZOLE AND 1,4-BENZOXAZINE DERIVATIVES

Citation
Dn. Nicolaides et al., REACTIONS OF O-METHYL O-QUINONE MONOOXIMES WITH METHYL-SUBSTITUTED, METHYLENE-SUBSTITUTED AND METHINE-SUBSTITUTED AROMATIC-COMPOUNDS - SYNTHESIS OF BENZO[D]OXAZOLE AND 1,4-BENZOXAZINE DERIVATIVES, Journal of heterocyclic chemistry, 34(6), 1997, pp. 1651-1656
Citations number
22
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
0022-152X
Volume
34
Issue
6
Year of publication
1997
Pages
1651 - 1656
Database
ISI
SICI code
0022-152X(1997)34:6<1651:ROOOMW>2.0.ZU;2-2
Abstract
O-Methyl o-quinone monoxime 1 reacts thermally with compounds 2a-d or 6a,b or 7a,b to give mainly the corresponding 2-substituted phenanthro xazoles 3a-c and 8. The reaction of 1 with aromatic methylene compound s 10a-c affords the ketones 13a-c in moderate to high yields. Similar products are also obtained from the reaction of monoximes 15a,b with s ome of the above reactants. The unexpected products 5 and 20 are obtai ned from the reaction of 1 with 2-methylimidazole (2d) and with phenyl oxirane (19) respectively, while the 4H-1,4-oxazine derivative 23 is o btained from the reaction of 1 with indene (21).