Novel syntheses of alpha-morpholinoamides from alpha,alpha-dichloroacetamides.
Dichloroacetamides, on heating with benzotriazole, morpholine, and triethylamine, produce, in a one-pot reaction, alpha-benzotriazolyl-alpha-morpholinoacetamides 4a,b. Intermediates 4a and 4b react with nucleophiles such as allylsilanes, silyl ethers, and organozinc reagents to afford diverse alpha-morpholinoamides.
Katritzky
Alan R
AR
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu
Zhang
Yuming
Y
Singh
Sandeep K
SK
D000081:Acetamides / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis; D009025:Morpholines / Q000138:chemical synthesis*; D014230:Triazoles / Q000737:chemistry
D000081:Acetamides; D000577:Amides; D009025:Morpholines; D014230:Triazoles; C012771:benzotriazole; C032619:2,2-dichloroacetamide