Intramolecular hydrogen bonding in phenolic amides enables direct synthesis of indolizines
Alhajaj Almaani1, Sulaiman Al-Shidhani1, Parisa Pakari Shalmani1
1Natural and Medical Sciences Research Center, University of Nizwa, Birkat Al Mauz, Nizwa, Sultanate of Oman. ahmadtak@unizwa.edu.om.
Abstract:
Herein, pyridinium 1,4-zwitterionic thiolates were treated with various chloroacetamides to form indolizines. Intramolecular hydrogen bonding in phenolic amides guides a stepwise [(5 + 1) - 1] cyclization that allows for the mild and efficient synthesis of these compounds. DFT calculations provided detailed insights into crucial interactions and structural characteristics. The theoretical and practical results confirmed the significant impact of intramolecular hydrogen bonding on the activation of the α-CH2 of the amide carbonyl group.
More Related Videos
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
14:11Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Related Concept Videos
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Benzene to Phenol via Cumene: Hock Process
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Diazonium Group Substitution: –OH and –H
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
