Next Article in Journal
Design, Synthesis and Antibacterial Evaluation of Some New 2-Phenyl-quinoline-4-carboxylic Acid Derivatives
Next Article in Special Issue
Microwave-Assisted Synthesis of Bioactive Six-Membered Heterocycles and Their Fused Analogues
Previous Article in Journal
A Peptoid-Based Fluorescent Sensor for Cyanide Detection
Previous Article in Special Issue
Hydrazonoyl Chlorides as Precursors for Synthesis of Novel Bis-Pyrrole Derivatives
Article Menu
Issue 3 (March) cover image

Export Article

Open AccessArticle
Molecules 2016, 21(3), 332; doi:10.3390/molecules21030332

Investigation of the Pyridinium Ylide—Alkyne Cycloaddition as a Fluorogenic Coupling Reaction

1
Department of Pharmacochemistry, Université Grenoble Alpes, CNRS, DPM UMR 5063, F-38041 Grenoble, France
2
Department of Chemistry, Physics and Environment, Faculty of Science and Environment, “Dunarea de Jos” University of Galati, 111 Domneasca Street, 800201 Galati, Romania
*
Authors to whom correspondence should be addressed.
Academic Editor: Philippe Belmont
Received: 26 January 2016 / Revised: 3 March 2016 / Accepted: 4 March 2016 / Published: 10 March 2016
(This article belongs to the Collection Heterocyclic Compounds)
View Full-Text   |   Download PDF [2260 KB, uploaded 10 March 2016]   |  

Abstract

The cycloaddition of pyridinium ylides with alkynes was investigated under mild conditions. A series of 13 pyridinium salts was prepared by alkylation of 4-substituted pyridines. Their reactivity with propiolic ester or amide in various reaction conditions (different temperatures, solvents, added bases) was studied, and 11 indolizines, with three points of structural variation, were, thus, isolated and characterized. The highest yields were obtained when electron-withdrawing groups were present on both the pyridinium ylide, generated in situ from the corresponding pyridinium salt, and the alkyne (X, Z = ester, amide, CN, carbonyl, etc.). Electron-withdrawing substituents, lowering the acid dissociation constant (pKa) of the pyridinium salts, allow the cycloaddition to proceed at pH 7.5 in aqueous buffers at room temperature. View Full-Text
Keywords: indolizine; coupling reaction; ylide; dipolar cycloaddition indolizine; coupling reaction; ylide; dipolar cycloaddition
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Bonte, S.; Ghinea, I.O.; Dinica, R.; Baussanne, I.; Demeunynck, M. Investigation of the Pyridinium Ylide—Alkyne Cycloaddition as a Fluorogenic Coupling Reaction. Molecules 2016, 21, 332.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top