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Some reactions of 1‐methyl‐(2‐phenylethyl)‐1,2,3,4‐tetrahydropyridines with organic azides. Synthesis of 1‐methyl‐(2‐phenylethyl)piperidylidene‐2‐sulfonamides
Author(s) -
Warren Brent K.,
Knaus Edward E.
Publication year - 1987
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.5570240537
Subject(s) - chemistry , organic chemistry , medicinal chemistry
The 1,3‐dipolar cycloaddition reaction of 1‐methyl‐ and 1‐(2‐phenylethyl)‐1,2,3,4‐tetrahydropyridines 7 with organic azides 8 afforded the respective 1‐substituted‐piperidylidene‐2‐sulfon(cyan)amides 9. Nitration of the 1‐(2‐phenylethyl) analogue 9o yielded the 1‐[2‐(4‐nitrophenyl)ethyl] derivative 9r which on reduction with palladium‐on‐charcoal and hydrazine gave the 1‐[2‐(4‐aminophenyl)ethyl] analogue 9s.