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Some reactions of 1‐alkyl‐1,2,3,4‐tetrahydropyridines with organic azides. Synthesis of 1‐alkylpiperidylidene‐2‐sulfonamides
Author(s) -
Warren Brent K.,
Knaus Edward E.
Publication year - 1988
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.5570250521
Subject(s) - chemistry , cycloaddition , azide , substituent , alkyl , medicinal chemistry , organic chemistry , catalysis
The 1,3‐dipolar cycloaddition reaction of 1‐substituted‐1,2,3,4‐tetrahydropyridines 4a‐d with organic azides 5 afforded the respective 1‐substituted‐piperidylidene‐2‐sulfonamides 6 . In contrast, the reaction of ( E )‐1‐(1‐propenyl)‐1,2,3,4‐tetrahydropyridine ( 4e ) with 4‐chlorobenzenesulfonyl azide yielded 6m as well as 1‐(4‐chlorophenyl)sulfonimine‐1,2,3,4‐tetrahydropyridine ( 7 ) arising from addition of the azide to the ( E )‐1‐(1‐propenyl) substituent of 4e .