Related Experiment Video
Updated: Aug 22, 2025

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Silver acetate-catalyzed synthesis of cyclic sulfonyl guanidine with exocyclic double bond
Dikshita Goswami1, Debashish Mishra1, Prodeep Phukan2
1Department of Chemistry, Gauhati University, Guwahati, Assam, 781014, India.
Abstract:
An efficient protocol for the synthesis of cyclic guanidine with exocyclic double bond has been developed. The synthesis has been achieved via intramolecular hydroamination of an intermediate propargyl guanidine by using silver acetate as catalyst in the presence of acetic acid. The reaction proceeds via the formation of acyclic propargyl guanidine in a one-pot reaction of N,N-dibromoarylsulfonamides, isonitriles, and propargylamine in the presence of K2CO3. In the second stage of the synthesis, the acyclic guanidine selectively undergoes 5-exo-dig cyclization in the presence of silver acetate and acetic acid to produce the five-membered cyclic guanidine framework having an exocyclic double bond as the constituent part. Short reaction time, wide substrate scope with good to high yields, and good functional group tolerance are the remarkable achievement of the present protocol.
More Related Videos
09:45Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
10:42Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Related Concept Videos
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 and Reactions of Sulfides
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction