Synthesis of methylpyridine derivatives (XXI). Amination of chloro-2,6-lutidines and their N-oxides via a hetaryne mechanism.

doi:10.1248/CPB.13.963

Paper

Synthesis of methylpyridine derivatives (XXI). Amination of chloro-2,6-lutidines and their N-oxides via a hetaryne mechanism.

Published Aug 25, 1965 · T. Kato, T. Niitsuma

Chemical & pharmaceutical bulletin

Q3 SJR score

9

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0

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Abstract

Reactions of chloro-2, 6-lutidines and their N-oxides with liquid ammonia in the presence of potassium amide proceed via a hetaryne mechanism to give 3-and 4-amino compounds. Amination of 3- as well as 4-chloro-2, 6-lutidine affords 3-amino-2, 6-lutidine as the main product (13∼15%) with a small amount of the 4-amino isomer. In the case of amination of their N-oxides, mole ratio of the resulting amino isomers is reverse to that in the case of chlorolutidines. 3-Chloro-2, 6-lutidine 1-oxide forms 4-amino-2, 6-lutidine 1-oxide as the main product (50%) with the 3-amino isomer as a by-product (13%), and reaction of 4-chloro-2, 6-lutidine 1-oxide gives 4-amino compound (34%) and the 3-amino isomer (6.5%).

Study Snapshot

This study demonstrates a hetaryne mechanism for amination of chloro-2,6-lutidines and their N-oxides, leading to 3- and 4-amino compounds with varying degrees of success.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Synthesis of methylpyridine derivatives (XXI). Amination of chloro-2,6-lutidines and their N-oxides via a hetaryne mechanism.

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