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Modification of pyridine‐3‐carboxamide (nicotinamide) by radical substitution
Author(s) -
Tada Masaru,
Yokoi Yurie
Publication year - 1989
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.5570260110
Subject(s) - chemistry , carboxamide , radical , isopropyl , pyridine , nicotinamide , alkylation , radical substitution , medicinal chemistry , reactivity (psychology) , stereochemistry , organic chemistry , medicine , alternative medicine , pathology , enzyme , catalysis
Pyridine‐3‐carboxamide ( 1 ) was reacted with alkyl radicals to give mono‐, di‐, and tri‐alkylated products. The t ‐butyl radical gives only 6‐ t ‐butylpyridine‐3‐carboxamide ( 4a ). The reactivity decreases in the order of t ‐butyl, isopropyl, and ethyl radicals. The product 4a reacts further with the 2‐phthalimidoethyl radical to give 2‐ and 4‐substituted products 9 and 10 , which were transformed into tetrahydronaphthyridinone derivatives 11 and 12 .