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Synthesis of N-(substituted phenylcarbonylamino)-4-ethyl-1,2,3,6-tetrahydropyridines as potential nonsteroidal anti-inflammatory agents

✍ Scribed by Kyoung Jin P. Yoon; Bala Kode; Lynneice Bowen; Kinfe K. Redda

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
95 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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.

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