5-Amino-3-imino-2,3-dihydrofurans and 3-Amino-5-imino-2,5-dihydrofurans from 4,4-Dialkyl-4-hydroxybut-2-ynenitriles
A novel general synthesis of the dihydrofurans 4 and 3b with nitrogen substituents in the 3- and 5-positions from 4,4-dialkyl-4-hydroxybut-2-ynenitriles 1 and primary and secondary amines is described.A 5-amino group reacts further with unchanged, or an excess of, hydroxybutynenitrile to give the difurylimines 6.
Landor, Stephen R.,Asobo, P. Forche,Fomum, Z. Tanee,Roberts, Ralph
p. 1201 - 1204
(2007/10/02)
Allenes. Part 42. Nucleophilic Addition of Hydroxylamine to Allenic and Acetylenic Nitriles; Synthesis of 3-Alkyl-5-amino, 5-Amino-3-phenyl, and 3-Amino-5-phenyl-isoxazoles
Hydroxylamine adds to allenic nitriles to give 3-alkyl-5-aminoisoxazoles in excellent yield.Hydroxyacetylenic nitriles similarly give 5-amino-3-(1-hydroxyalkyl)isoxazoles.Phenylpropynenitrile under varying conditions of temperature and solvent yields mainly 5-amino-3-phenylisoxazole with varying amounts of 3-amino-5-phenylisoxazole as a by-product.
Fomum, Z. Tanee,Asobo, P. Forsche,Landor, Stephen R.,Landor, Phyllis D.
p. 1079 - 1083
(2007/10/02)
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