1,2-Oxazines, 1,2-benzoxazines and related compounds

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Abstract

This chapter reviews the literature for 1,2-oxazines, 1,2 benzoxazines, and related compounds, which can be synthesized by the dehydration of 5,6-dihydro-6-hydroxy-4H-1,2-oxazines. The latter are obtained from the cyclization of 3-acyl-1-nitrosopent-1-en-4-ones (or their oximino tautomers) by heating them with urea in boiling methanol, or ethanol. The method of preparation of 6H-1,2-oxazines is discussed. Examples are provided to emphasize the importance of the oxazinium salts as electrophiles; this is supported with schematic structure diagrams. The descriptions of synthesis of oxazines, their use as chiral synthons, and general reactions are also presented. The reduction of 1, 2-oxazines derivative is explained with examples. In certain reactions, the corresponding 1,2-oxazanes seem to be implicated as intermediates in certain reaction types and this is illustrated with an example.
Original languageEnglish
Title of host publicationSecond Supplements to the 2nd Edition of Rodd's Chemistry of Carbon Compounds
Subtitle of host publicationA Modern Comprehensive Treatise
Pages359-383
Number of pages25
Volume4
Edition2
DOIs
Publication statusPublished - 1991

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    Sainsbury, M. (1991). 1,2-Oxazines, 1,2-benzoxazines and related compounds. In Second Supplements to the 2nd Edition of Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise (2 ed., Vol. 4, pp. 359-383) https://doi.org/10.1016/B978-044453347-0.50210-X