Upender K. Nadir

Synthesis of Functionalized N‐Arylsulfonyl Aziridines from α,β‐Unsaturated Esters, Amides, Ketones, and Nitriles Using N,N‐Dichloroarylsulfonamides as Nitrogen Source

Abstract A convenient and general aziridination process has been developed for the synthesis of functionalized N‐arylsulfonylaziridines bearing an alkoxycarbonyl, acyl, cyano, and carboxamide group at C2. The two‐step sequence involves addition of N,N‐dichloroarylsulfonamide to the appropriate olefin in the presence of Cu(acac)2, treatment of the resultant chlorosulfonamide with Na2SO3, followed by cyclization with NaOH to give the appropriate aziridine in good yields. The reaction is found to be an anti‐stereoselective.

Regiospecific cycloaddition reaction of 2-aryl and 2-alkyl 1-arenesulfonylaziridines with isocyanates using sodium iodide

Abstract Reaction of tittle aziridines with isocyanates in presence of sodium iodide is regiospecific. 2-aryl N-sulfonylaziridines give the 1-N-arylsulfonyl-3-alkyl/aryl-4-phenyl-2-imidazolidinones exclusively whereas the 2-alkyl substituted aziridines afford only the 1-N-alkyl/aryl-3-N-arylsulfonyl-4-alkyl-2-imidazolidinones.

Reaction of 2,3-disubstituted-N-arylsulfonylaziridines with isocyanates in presence of sodium iodide - stereospecific conversion of N-arylsulfonylaziridines to imidazolidinones

Abstract The reaction of 2,3-disubstituted arylsulfonylaziridines with isocyanates in presence of sodium iodide yielding 4,5-disubstituted-2-imidazolidinones is somewhat specific rather than a general reaction, but whenever the reaction occurs, it does so in a totally stereospecific manner where imidazolidinones produced have the same geometric configuration as that of the starting aziridines. The yield of the imidazolidinones varies (0 to 60%) depending on the nature of the substituent on the aziridine ring carbon as well as their geometry.

Microwave-Assisted Efficient Methylation of Alkyl and Arenesulfonamides with Trimethylsulfoxonium Iodide and KOH

Abstract A solvent-free synthesis of N-methyl and N,N-dimethylsulfonamides has been achieved by treating the primary and secondary sulfonamides with Me3S+OI− and KOH under microwave irradiation on alumina support.

Synthesis of 2-Benzoyl-3-aryl-N-arylsulphonylaziridines from the Reaction of N-Arylsulphonylimines with Dimethylsulphonium Phenacylide - The First Example of A Functionalized-Methylene Transfer to Azomethines

Abstract The first example of phenacyl group transfer from dimethylsulphonium phenacylide to N-arylsulphonylimines to yield 2-benzoyl-1-arylsulphonylaziridines is described.

Microwave-Assisted Regioselective Synthesis of trans-1-Arenesulfonyl-2-ethoxycarbonyl-3-phenylazetidines

An efficient regioselective synthesis of trans-1-arenesulfonyl-2-ethoxycarbonyl-3-phenylazetidines has been achieved through microwave-assisted reactions of 1-arenesulfonylaziridines with dimethylsulfonium carboethoxymethylide using alumina as solid support.