Synthesis of new 5-nitrotetrahydro-1,3-oxazine derivatives via electron-transfer reactions
1989; Elsevier BV; Volume: 45; Issue: 17 Linguagem: Inglês
10.1016/s0040-4020(01)89494-1
ISSN1464-5416
AutoresMichel P. Crozeta, Patrice Vanelle,
Tópico(s)Chemical Reaction Mechanisms
ResumoAbstract 5-Nitrotetrahydro-1,3-oxazine salts are found to be useful nucleophiles for S RN 1 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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