N,N’-Substituted 1,2,5 Thiadiazolidine 1,1-Dioxides: Synthesis, Selected Chemical and Spectral Proprieties and Antimicrobial Evaluation †

Abstract

The sulfamide functional group is increasingly relevant in both medicinal and bioorganic chemistry. We report here practical access to a series of N2,N5-substituted five-membered cyclosulfamides. The five-membered heterocyclic motif was prepared starting from proteogenic amino acids and chlorosulfonyl isocyanate via the Mitsunobu reaction. Selected chemical and spectral proprieties and the antimicrobial evaluation of these compounds are detailed.

A simple and highly efficient solvent- and catalyst-free synthesis of novelN-sulfamoyl imines

“…For an efficient process to the required sulfamoyl imines, we used the chemistry of chlorosulfonyl isocyanate (CSI) developed by our group (41)(42)(43)(44)(45) to access at the intermediate sulfamides. The preparation of N-Boc sulfamides is performed in dried dichloromethane with successive additions of tert-butanol and chloroethylamine or N,N-bis-chloroethylamine into CSI.…”

Synthesis of New Fused Benzothiadiazepines and Macrocyclic Sulfamides Starting from N,N-Disubstituted Sulfamides and N(Boc)-Sulfamides

“…The synthesis of the key intermediates N(Boc) , N ′-alkyl-sulfamide ( 2a-f ) and N- ((Boc)sulfamoylamino)carboxylates ( 2g-j ) was accomplished as shown in Scheme 1. The carbamylation of chlorosulfonyl isocyanate with tert -butyl alcohol at 0°C in dichloromethane followed by in situ sulfamoylation with the corresponding amine, amino acid ester hydrochloride, or diamine in the presence of triethylamine (TEA) gave the desired N(Boc) , N ′(alkyl)sulfamide ( 2a-b ), N (Boc), N ′-sufamoylamino acid esters ( 2g-j ) or bis -carboxylsulfamides ( 2c-f ) [28, 29]. …”

Copper-(s)-N-methylpyrrolidine-2-carboxylate catalyzed N-Arylation of N⁵h-1,2,5-thiadiazolidine 1,1-dioxides

“…Our studies have focused on the preparation of substituted cyclic sulfamides [12][13][14][15]. As a continuation of this research interest, here we report our results regarding the synthesis of N-arylthiadiazolidine 1,1-dioxides via C(sp2)-N(sp2) bond formation using…”

“…Starting N 2 -substituted, N 5 H -1,2,5-thiadiazolidines were prepared from the chlorosulfonyl isocyanate (CSI) according to established synthetic procedures [12][13][14][15][18][19][20].…”