Synthesis of Perhydro-1,3-diazine-2-thiones from β-Chloro Imines

Article abstract of DOI:10.1021/jo00272a024

The reaction of β-chloro imines with methanol gave rise to β-alkylamino acetals via intermediate 2-methoxyazetidines.If an aromatic β-chloro imine was used under these conditions, 1-methoxy-2-methyl-1-phenyl-1-propene was also formed.The reaction of β-chloro imines with potassium thiocyanate in methanol gave rise to perhydro-1,3-diazine-2-thiones in 10-55percent yield in addition to β-alkylamino acetals, again via methoxyazetidines.