Related Experiment Video
Updated: May 5, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Synthesis of N-heterocyclic compounds using N,N-dimethylacetamides as an electrophilic carbon source
Dayoung Chun1, Seok Beom Lee2, Simin Chun1
1Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul, 08826, Republic of Korea. schong17@snu.ac.kr.
Abstract:
In this study, N-heterocyclic compounds were synthesized using nitrogen-containing nucleophilic substrates and electrophilic carbon sources derived from N,N-dimethylacetamide (DMAc). Depending on the nucleophilic groups, N-heterocyclic compounds such as 4-quinazolinones, pyrrole-quinoxalines, and dihydro-benzothiadiazine dioxides were produced. Carbon, adjacent to the nitrogen in DMAc, was activated in the presence of FeCl3·6H2O and di-t-butyl peroxide (DTBP). This procedure was considered an economical synthetic method because it utilized iron catalysts and DMAc as an electrophilic carbon source and a solvent.
More Related Videos
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
07:06A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Related Concept Videos
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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...
Preparation of Nitriles
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
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...