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Synthesis and structure of the N ‐alkyl‐2,6‐dimethyl‐4‐oxopyridine‐3‐carboxylic acids
Author(s) -
Dobbin Paul S.,
Hider Robert C.,
Venkatramani Lalitha,
Siripitayana Jintana,
van der Hel Dick
Publication year - 1993
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.5570300323
Subject(s) - chemistry , alkyl , intramolecular force , ring (chemistry) , amine gas treating , medicinal chemistry , primary (astronomy) , carboxylate , hydrogen bond , carboxylic acid , alkylation , organic chemistry , molecule , catalysis , physics , astronomy
A range of N ‐alkyl‐2,6‐dimethyl‐4‐oxopyridine‐3‐carboxylic acids XV have been prepared via reactions of primary alkyl amines with differing 2,6‐dimethyl‐4‐oxopyran‐3‐carboxylate esters IX . The quantity of desired product formed and the character of by‐products formed are determined by the natures of the amine and ester IX respectively. X‐ray crystallography data for the N ‐ethyl analogue of XV indicates very strong intramolecular hydrogen bonding to be present, with the heterocyclic ring exhibiting considerable aromaticity.