The Reaction of 4,5-Dichloro-1,2,3-dithiazolium Chloride with Sulfimides: A New Synthesis of N-Aryl-1,2,3-dithiazolimines

Andreas S Kalogirou,Panayiotis A Koutentis

doi:10.3390/molecules14072356

Abstract

N-Aryl-S,S-dimethylsulfimides 3 (Ar = 4-NO2C6H4), 4 (Ar = Ph) and 5 (Ar = 4-Tol) react with Appel salt 1 to give the corresponding N-aryl-(4-chloro-5H-1,2,3-dithiazolylidene)benzenamines 8 (Ar = 4-NO2C6H4), 9 (Ar = Ph) and 10 (Ar = 4-Tol) in 84, 94 and 87% yields, respectively. The reaction proceeds in the absence of base and a proposed reaction mechanism is given.

Highlights

N-Aryl-1,2,3-dithiazol-5H-imines show interesting antitumour [1], antibacterial [2,3,4], antifungal [57], and herbicidal [8] activities
The biological activity could be due to the 1,2,3-dithiazole ring, which acts as a powerful inhibitor of several enzymes that are structurally related to serine proteases [9]
In view of their use as N-transfer reagents to electrophiles, we examined an alternative route to N-aryl-1,2,3-dithiazolimines by reacting N-aryl-S,S-dimethylsulfimides with Appel salt 1

Summary

Introduction

N-Aryl-1,2,3-dithiazol-5H-imines show interesting antitumour [1], antibacterial [2,3,4], antifungal [57], and herbicidal [8] activities. Molecules 2009, 14 as with arylamides [22], heteroarylamines [21,23] or alkylamines [20,21], the reactions are low yielding or complex. For example sulfimides react with nitrile oxides to afford 1H-l,2,4-triazole 2-oxides [24], and react with alkoxychromium (Fischer) carbenes to form imidates [25]. In view of their use as N-transfer reagents to electrophiles, we examined an alternative route to N-aryl-1,2,3-dithiazolimines by reacting N-aryl-S,S-dimethylsulfimides with Appel salt 1

Results and Discussion

Method

Conclusions

General

Reactions of Appel salt 1 with sulfimides

Reactions of Appel salt 1 with anilines