Reaction of Salicylamine with α-Dicarbonyl Compounds. II. Formation of 2,2′-Bibenz-1,3-oxazines
- 1 January 1970
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 43 (1) , 226-231
- https://doi.org/10.1246/bcsj.43.226
Abstract
The compounds of a new type, 2,2′-bibenz-1,3-oxazine and its derivatives have been synthesized by the reactions of salicylamines with glyoxal or α-diketones in methanol at a temperature lower than 20°C. The oxazine structures were confirmed by infrared spectroscopy in solid state and by NMR spectroscopy in CCl4, CDCl3 and chlorobenzene. An oxazine-Schiff base equilibrium was observed in pyridine and in hot chlorobenzene by NMR spectra. It was found that hydrolytic decomposition of 2,2′-dimethyl-2,2′-bibenzoxazine leads to the formation of salicylidenesalicylamine through transamination. The mechanisms were investigated spectrophotometrically.Keywords
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