Tetrahedron p. 5477 - 5484 (1989)
Update date:2022-09-26
Topics:
Crozet, Michel P.
Vanelle, Patrice
5-Nitrotetrahydro-1,3-oxazine salts are found to be useful nucleophiles for SRN1 reactions with p-nitrobenzyl chloride, 2,2-dinitropropane and 1-methyl-2-chloromethyl-5-nitroimidazole.From C-alkylation products, base promoted nitrous acid elimination and electron-transfer elimination of the two nitro groups afford new tetrahydro-1,3-oxazines with respectively a tri- and tetrasubstituted double bond at the 5 position.These new tetrahydro-1,3-oxazines can be hydrolysed to the corresponding ethylenic aminoalcohols by heating with hydrochloric acid.
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