SYNTHESIS OF NEW 5-NITROTETRAHYDRO-1,3-0XAZINE DERIVATIVES VIA ELECTRON-TRANSFER REACTIONS

Article abstract of DOI:10.1016/S0040-4020(01)89494-1

5-Nitrotetrahydro-1,3-oxazine salts are found to be useful nucleophiles for S_RN1 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.