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Synthesis of N ‐(substituted phenylcarbonylamino)‐4‐ethyl‐1,2,3,6‐tetrahydropyridines as potential nonsteroidal anti‐inflammatory agents
Author(s) -
Yoon Kyoung Jin P.,
Kode Bala,
Bowen Lynneice,
Redda Kinfe K.
Publication year - 2001
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570380110
Subject(s) - chemistry , sodium borohydride , pyridinium , ethanol , nonsteroidal , medicinal chemistry , ethyl ester , borohydride , organic chemistry , catalysis , pharmacology , medicine
Fourteen novel N ‐(substituted phenylcarbonylamino)‐4‐ethyl‐1,2,3,6‐tetrahydropyridines 9 were synthesized in fair to good yields. 4‐Ethylpyridine 5 reacted with O ‐mesitylenesulfonylhydroxylamine ( O ‐MSH) 4 to furnish N ‐amino‐4‐ethylpyridinium mesitylenesulfonate 6 . The reaction of 6 with substituted acid chlorides 7 gave the stable crystalline pyridinium ylides 8a‐8n . A sodium borohydride reduction of 8 in absolute ethanol furnished the target compounds N ‐(substituted phenylcarbonylamino)‐4‐ethyl‐1,2,3,6‐tetrahydropyridines 9a‐9n .