A Convenient Synthesis of Aryl-Substituted N-Carbamoyl/N-Thiocarbamoyl Narcotine and Related Compounds

Abstract

The reaction of nornarcotine and 5-bromonornarcotine, synthesized from noscapine, with suitable aromatic isocyanates or isothiocyanates provides a general method for the synthesis of aryl-substituted N-carbamoyl or N-thiocarbamoylnarcotine and related compounds. Similarly, 15a has been prepared via the reduction of the lactone ring moiety of noscapine. Also, an improved procedure, which utilizes narcotine N-oxide⋅HCl for generation of nornarcotine, is described.