Two Novel Microwave‐Promoted Reactions between Ethyl 6‐Acetylpyridine‐2‐carboxylate and Aromatic Amine/Aliphatic Amine

Abstract

The unsymmetric precursor ethyl 6‐acetylpyridine‐2‐carboxylate (3) was synthesized from 2,6‐dipiclinic acid (1). On the basis of this precursor, two distinctively different types of compounds were prepared by microwave irradiation under solvent‐free conditions. One type was mono(imino)pyridine compounds (4a–4f), originating from the Schiff base condensation between a series of aromatic amines and the precursor 3; another type was 6‐acetylpyridine‐2‐carboxamide compounds (5a–5c), which were the products of amidation reactions between a series of aliphatic amines and the same precursor 3.

Keywords:

• amidation reaction
• ethyl 6‐acetylpyridine‐2‐carboxylate
• microwave irradiation
• reaction mechanism
• Schiff base condensation

Acknowledgment

We are grateful to the Chinese Academy of Science, the Natural Science Foundation of China (No. 20371039), National Basic Research Program (the 973 Program, No. 2003CB214600), the Program for Changjiang Scholars and Innovative Research Team in University, PCSIRTU (IRT0559), the Key Laboratory Research and Establishment Program of Shaanxi Education Section (No. 03JS006), and the Natural Science Foundation of Shaanxi Education Section (No. 04JK143) for financial support.