N‐bis(methylthio)methylene derivatives. 5. New synthesis of 2‐aminoindolizine and related compounds via a formal [3 + 3] cycloaddition reaction using N‐bis(ethoxycarbonylmethylthio)methylenephenylsulfonamides

Abstract

Reaction of pyridinium N‐ylide 5a with N‐bis(ethoxycarbonyl)methylthio)(p‐substituted‐phenyl)sulfon‐amides 2a,c in the presence of triethylamine as a base in ethanol gave diethyl 2‐(p‐substituted‐phenylsulfonyl)aminoindolizine‐1,3‐dicarboxylates 9a,b via a new formal [3 + 3] cycloaddition reaction. In a similar manner, 2‐sulfonylaminopyrrolo[2,1‐a]isoquinoline derivatives 11a‐e were also obtained by the reaction of 2a‐c and 4a,b with the corresponding isoquinoline N‐ylides 10a.b with good results.

4-Amino-substituted Benzenesulfonamides as Inhibitors of Human Carbonic Anhydrases

“…Diethyl 4-aminophenylsulfonylcarbonimidodithioate ( 2 ) was synthesized from 4-aminobenzene-1-sulfonamide ( 1 ) by treating it with carbon disulfide and then with ethyl iodide [25] (Scheme 1). N -Substituted-β-alanine 3 [26] was obtained in the reaction of 1 with acrylic acid in aqueous solution in the presence of a catalytic amount of hydroquinone, whereas the reaction of 2 with acrylic acid in a mixture of toluene and acetic acid provided 3-[(4-{[bis(ethylthio)-methylene]sulfamoyl}phenyl)amino]propanoic acid ( 4 ).…”

Synthesis and Reactivity of Unsymmetrical S , S ″ -Dialkyl N -(Arenesulfonyl)Carbondithioimidates

“…The synthesis of symmetrical S,S 0 -dialkyl N-(arenesulfonyl)carbondithioimidates and their use as building blocks for heterocycles were studied in great detail and complexity [1][2][3][4], whereas unsymmetrically alkylated representatives have rarely been taken into consideration [5,6]. As new building blocks bearing sulfonylimino groups, compounds of the latter type are particularly suitable [7].…”