Copper-Catalyzed One-Pot Synthesis of N-Sulfonyl Amidines from Sulfonyl Hydrazine, Terminal Alkynes and Sulfonyl Azides.

Yu Zhao,Zitong Zhou,Weiguang Yang,Man Chen

doi:10.3390/molecules26123700

Abstract

N-Sulfonyl amidines are developed from a Cu-catalyzed three-component reaction from sulfonyl hydrazines, terminal alkynes and sulfonyl azides in toluene at room temperature. Particularly, the intermediate N-sulfonylketenimines was generated via a CuAAC/ring-opening procedure and took a nucleophilic addition with the weak nucleophile sulfonyl hydrazines. In addition, the stability of the product was tested by a HNMR spectrometer.

Highlights

IntroductionAmidine derivatives derivatives are are important important privileged privileged scaffolds scaffolds in in medicinal medicinal chemistry [1–3], synthetic chemistry [4]
N-sulfonyl amidines amidines involved in the reaction of cyclic thioamides and thioacetamide derivatives with sulfonyl involved in the reaction of cyclic thioamides and thioacetamide derivatives with sulazides
When changing the substrates 1 to other corresponding products 4g–4m with yields of 73–89% and 4n–4q with yields of 78–86%, in sulfonyl hydrazines, such as 1g–1k, it could not obtain the desired products and give dewhich both the substituents led to high yields and were influenced slightly

Summary

Introduction

Amidine derivatives derivatives are are important important privileged privileged scaffolds scaffolds in in medicinal medicinal chemistry [1–3], synthetic chemistry [4]. N-sulfonyl amidines and their functionalizations is highly required. N published maps and institutional affilcensee MDPI, Basel, Switzerland. N-sulfonyl amidines amidines involved in the reaction of cyclic thioamides and thioacetamide derivatives with sulfonyl involved in the reaction of cyclic thioamides and thioacetamide derivatives with sulazides [14,16–18], the phosphite-mediated. The sulfonamide reaction with formamide [21] and the sulfonyl ynamide rearrangement [22]. Cu-catalyzed multicomponent reaction of terminal alThe most thethe reaction of terminal alkynes, kynes, sulfonyl and amines, has been applied to synthesize numerous oxysulfonyl azidesazides and amines, whichwhich has been applied to synthesize numerous oxygengen-containing nitrogen-containing heterocyclic compounds [23–31]. Could take a mediate generated by Cu-catalyzed alkynes and sulfonyl azides [31–33] could take a nuclenucleophilic addition reaction with most amines, as show in Scheme. Copper-catalyzed reactionsalkynes, of the terminal sulfonyl azides and amines

Results

General

Compound Characterizations and Preparations

Conclusions