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Intramolecular nucleophilic cyclization of 3‐substituted pyridylalkylamines onto the 2‐position of the pyridine ring
Author(s) -
Hawes Edward M.,
Davis Hubert Lome
Publication year - 1973
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.5570100109
Subject(s) - chemistry , butylamine , sodium hydride , yield (engineering) , medicinal chemistry , intramolecular force , nucleophile , pyridine , azepine , hydride , ring (chemistry) , reagent , sodium , alkali metal , amide , potassium , propylamine , stereochemistry , organic chemistry , metal , catalysis , materials science , amine gas treating , metallurgy
The intramolecular nucleophilic cyclization of 4‐(3‐pyridyl)butylamine ( 4a ) to yield 6,7,8,9‐tetrahydro‐5 H ‐pyrido[2,3‐ b ]azepine ( 5 ) was investigated. Of eleven different alkali metal reagents sodium, sodium hydride, sodium amide, and potassium hydride gave good yields of 5 . The sodium conditions when applied to 3‐(3‐pyridyl)propylamine ( 4b ) afforded 1,2,3,4‐tetrahydro‐1,8‐naphthyridine ( 6 ) in good yield.