A general and convenient synthesis of 4-(tosylmethyl)semicarbazones and their use in amidoalkylation of hydrogen, heteroatom, and carbon nucleophiles

Add time:09/07/2019    Source:sciencedirect.com

A general synthesis of previously unknown semicarbazone-based α-amidoalkylating reagents, 4-(tosylmethyl)semicarbazones, has been developed. The synthesis involved three-component condensation of semicarbazones of aliphatic or aromatic aldehydes with the same or other aldehydes and p-toluenesulfinic acid. The scope and limitations of this reaction were investigated. The compounds obtained were demonstrated to be an efficient α-(4-semicarbazono)alkylating agents. They were reacted with H- (sodium borohydride), O- (sodium methylate), S- (sodium phenylthiolate), N- (pyrrolidine, sodium succinimide), P- (trialkyl phosphites), and C-nucleophiles (sodium diethyl malonate) to give the corresponding products of the tosyl group substitution, 4-substituted semicarbazones, including analogues of nitrofurazone. Among the prepared compounds tested in vitro for antibacterial and antifungal activity, three nitrofuryl-containing semicarbazones exhibited high biological activities with minimum inhibitory concentration (MIC) values of 8–32 μg/mL.

We also recommend Trading Suppliers and Manufacturers of (2E)-2-Decenal semicarbazone (cas 16742-25-9). Pls Click Website Link as below: cas 16742-25-9 suppliers

Prev:Syntheses and reactions of 5-O-acetyl-1,2-anhydro-3-O-benzyl-α-d-ribofuranose and -β-d-lyxofuranose, 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl- and 1,2-anhydro-5,6-di-O-benzoyl-3-O-benzyl-β-d-mannofuranose, and 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-α-d-glucopyranose and -β-d-talopyranose
Next:Antituberculous activity of some aryl semicarbazone derivatives)