ChemInform Abstract: Reactions of O-Methyl o-Quinone Monoximes with Methyl-, Methylene- and Methine-Substituted Aromatic Compounds. Synthesis of Benzo[d]oxazole and 1,4-Benzoxazine Derivatives.

✍ Scribed by D. N. NICOLAIDES; R. W. AWAD; G. K. PAPAGEORGIOU; E. KOJANNI; C. A. TSOLERIDIS

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 39 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199820070

✦ Synopsis

Reactions of O-Methyl o-Quinone Monoximes with

Methyl-, Methylene-and Methine-Substituted Aromatic Compounds. Synthesis of Benzo[d]

oxazole and 1,4-Benzoxazine Derivatives.

-Monoxime (I) reacts with heteroaryl derivatives (II), (V), and (VIII), with methylene derivatives (XII) and (XIII) or methine derivatives (X) to give mainly the 2-substituted phenanthroxazoles (III), (IX) and (XI). Reaction of (I) with aromatic methylene compounds (XIII) furnishes the ketones (XIV) in moderate to good yields. Unexpected products (e.g. (VII)) are also obtained. A 4H-1,4-oxazine derivative (XVI) is synthesized from (I) and indene. The reaction of monoximes with (XIII) can be considered as a method for the conversion of methylene compounds to ketones in neutral media. -(NICOLAIDES, D. N.;