Vilsmeier−Haack Reactions of 2-Arylamino-3-acetyl-5,6-dihydro-4H-pyrans toward the Synthesis of Highly Substituted Pyridin-2(1H)-ones

A facile and efficient one-pot synthesis of highly substituted pyridin-2(1H)-ones was developed via Vilsmeier−Haack reactions of readily available enaminones, 2-arylamino-3-acetyl-5,6-dihydro-4H-pyrans, and a mechanism involving sequential ring-opening, haloformylation, and intramolecular nucleophil...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2007-10, Vol.72 (22), p.8593-8596
Main Authors: Xiang, Dexuan, Yang, Zhang, Rui, Liang, Yongjiu, Pan, Wei, Huang, Jie, Dong, Dewen
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Kinetics and mechanisms
Molecular Structure
Organic chemistry
Preparations and properties
Pyrans - chemistry
Pyridones - chemical synthesis
Pyridones - chemistry
Reactivity and mechanisms
Stereoisomerism
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A facile and efficient one-pot synthesis of highly substituted pyridin-2(1H)-ones was developed via Vilsmeier−Haack reactions of readily available enaminones, 2-arylamino-3-acetyl-5,6-dihydro-4H-pyrans, and a mechanism involving sequential ring-opening, haloformylation, and intramolecular nucleophilic cyclization reactions is proposed.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo7015482