Oxidations with lead tetraacetate. II. .DELTA.3-1,3,4-Oxadiazolines from oxocarbohydrazones and a .DELTA.3-1,3,4-thiadiazoline from acetone thiocarbohydrazone
Catalytic hydrophosphorylation of semicarbazones, thiosemicarbazones, carbonohydrazones, and oxalyldihydrazones
作者:E. D. Matveev、T. A. Podrugin、I. V. Sharutin、N. S. Zefirov
DOI:10.1007/s11172-012-0054-1
日期:2012.2
Reaction of diethyl phosphite with semicarbazones, thiosemicarbazones, carbonohydrazones, and oxalyldihydrazones of aliphatic and carbocyclic ketones catalyzed by [tetra(tert-butyl)phthalocyanine]aluminum chloride resulted in hydrophosphorylation of the C=N bonds of hydrazones under study.
A green synthetic method for 1,5-disubstituted carbohydrazones is described. The reaction of dimethyl carbonate with hydrazine hydrate first gave carbohydrazide, which further reacted with various aromatic aldehydes or aliphatic ketones under solvent-free conditions to efficiently afford 1,5-disubstituted carbohydrazone. This protocol has the advantages of using nontoxic dimethyl carbonate as starting material, no use of organic solvents, short reaction time, high yield, and simple workup procedure.