A novel route for a SnCl 2 -promoted tandem reduction, ammonolysis, condensation, and deamination reaction which uses nitrile and 2-nitro-N-phenylbenzenesulfonamide/N-(2-nitrophenyl)benzenesulfonamide to synthesize derivatives of benzothiadiazine/1-(phenylsulfonyl)-1H-benzimidazole has been developed. The method features convenient operation and good functional group tolerance. In addition, it employs unsensitive and inexpensive SnCl 2 /i-PrOH as the reaction reagent and provides a direct approach for the synthesis of pharmaceutically important targets.
Cyanoimines (C=NÀ CN) are eliciting increased attention because of their extensive presence in medicine and biologically active molecules. This study demonstrated the use of the electrochemical oxidative carbon-atom multifunctionalization and N-cyanation of imine to synthesize (Z)-N'-cyano-N-carbamimidothioate. This multicomponent reaction showed good step economy, thereby providing a tool to construct various cyanoimines. Moreover, good functional-group tolerance and large-scale synthesis were achieved under metal-free and external-oxidant-free conditions, indicating the potential applicability of this methodology.
A novel route for an iron-catalyzed tandem sulfonylation, C(sp 2 )−H activation, cyclization reaction which uses Nphenyl-N-(prop-2-yn-1-yl)benzenesulfonamide and benzenesulfonohydrazide to synthesize derivatives of (Z)-2-phenyl-4-((phenylsulfonyl)methylene)-3,4-dihydro-2H-benzo[e][1,2]thiazine 1,1-dioxide has been developed. The method features convenient operation and good functional group tolerance. In addition, it employs insensitive and inexpensive FeSO 4 as the catalyst and provides a direct approach for the preparation of benzothiazides.
Sulfonamides and
lipids are widely found in natural products, bioactive
substances, and pharmaceuticals. Here, we report
N
-sulfonylation and esterification of carboxylic acids in an environment-friendly
one-pot tandem protocol involving 1,2-dichloroethane (DCE). Moreover,
1,8-diazabicyclo (5.4.0) undec-7-ene was necessary for this reaction
as a strong base, which drives the reaction to completion. Although
DCE is a very low activity reagent, it acts not only as a solvent
but also as a reactant in the reaction. The β-chloroester contained
in the reaction product can be easily dissociated to react with N,
S, and O atoms, increasing the possibility for subsequent synthesis.
A novel route involving the metal-promoted tandem nitration and halogenation of N-phenylbenzenesulfonamide to synthesize N-(4-halo-2-nitrophenyl)benzenesulfonamide derivatives has been developed.
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