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Literature DB >> 26029797

Base-Promoted β-C(sp(3))-H Functionalization of Enaminones: An Approach to Polysubstituted Pyridines.

Jinhai Shen, Dingding Cai, Changsheng Kuai, Yunqi Liu, Ming'e Wei, Guolin Cheng, Xiuling Cui.

Abstract

A convenient "one-pot" base-promoted synthesis of polysubstituted pyridines from 1-arylethylamines and ynones through the direct β-C(sp(3))-H functionalization of enaminones under metal-free conditions has been developed. An intermolecular Michael addition reaction and an intramolecular condensation were involved in this procedure, which features high regioselectivity, high efficiency, and environmental friendliness. Various polysubstituted pyridines were provided in up to 92% yield for 34 examples.

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Year: 2015 PMID： 26029797 DOI： 10.1021/acs.joc.5b00635

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

5 in total

1. 4,6-Dihydroxysalicylic Acid-Catalyzed Oxidative Condensation of Benzylic Amines and Aromatic Ketones for the Preparation of 2,4,6-Trisubstituted Pyridines and Its Application to Metal-Free Synthesis of G-Quadruplex Binding Ligands.

Authors: Chun-Ping Dong; Shintaro Kodama; Akihiro Nomoto; Michio Ueshima; Akiya Ogawa
Journal: ACS Omega Date: 2019-05-23

2. Retracted Article: An efficient one pot three-component synthesis of 2,4,6-triarylpyridines using triflimide as a metal-free catalyst under solvent-free conditions.

Authors: Hongshe Wang; Weixing Zhao; Juan Du; Fenyan Wei; Qi Chen; Xiaomei Wang
Journal: RSC Adv Date: 2019-02-12 Impact factor: 3.361

Base-Promoted β-C(sp(3))-H Functionalization of Enaminones: An Approach to Polysubstituted Pyridines.

1. 4,6-Dihydroxysalicylic Acid-Catalyzed Oxidative Condensation of Benzylic Amines and Aromatic Ketones for the Preparation of 2,4,6-Trisubstituted Pyridines and Its Application to Metal-Free Synthesis of G-Quadruplex Binding Ligands.

2. Retracted Article: An efficient one pot three-component synthesis of 2,4,6-triarylpyridines using triflimide as a metal-free catalyst under solvent-free conditions.

3. Metal-free cascade synthesis of unsymmetrical 2-aminopyrimidines from imidazolate enaminones.

4. PIDA-mediated intramolecular oxidative C-N bond formation for the direct synthesis of quinoxalines from enaminones.

5. Crystal structure and Hirshfeld surface analysis of 4-(3-meth-oxy-phen-yl)-2,6-di-phenyl-pyridine.