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A Convenient Synthesis of Aryl‐Substituted N ‐Carbamoyl/ N ‐Thiocarbamoyl Narcotine and Related Compounds
Author(s) -
Aggarwal Shefali,
Ghosh Narendra N.,
Aneja Ritu,
Joshi Harish,
Chandra Ramesh
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200208)85:8<2458::aid-hlca2458>3.0.co;2-l
Subject(s) - chemistry , noscapine , moiety , aryl , ring (chemistry) , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , alkyl , alkaloid
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.