A green, mild and efficient one-pot method for the synthesis of sulfonamides from thiols and disulfides in water

Abstract

A general, mild, convenient and environmentally benign method was developed for the synthesis of various N-aryl and N-alkyl sulfonamides in water. Trichloroisocyanuric acid (TCCA) was used for the oxidative chlorination of disulfides and thiols to produce the corresponding sulfonyl chloride, which reacted in situ with different amines in the absence of organic bases, to furnish sulfonamides in good to excellent yields. The isolation of the products involves simple experimental conditions and a product isolation procedure (only filtration) in the absence of organic solvents, which makes this protocol potentially useful in the development of a green strategy for the synthesis of sulfonamides.

7.28 Oxidation of Sulfur, Selenium, and Tellurium

“…A more environmentally benign and cheaper oxidation of thiols or disulfides to sulfonamides is provided by TCCA in water followed by the addition of K 2 CO 3 and the proper amine. 102 The one-pot oxidative halogenation of thiols to sulfonyl chlorides and sulfonyl fluorides can be performed by other systems such as TMSCl/KNO 3 , 103 N-chlorosuccinimide (NCS), 104 ClO 2 ,105 or NaOCl/KHF 2 . 106 A useful application of the NaOCl/KHF 2 system is the selective synthesis of difficult-to-access heteroaryl sulfonamides from heteroaryl thiols.…”

N-Acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides: highly selective and efficient reagents for acylation of amines in water

“…In continuation of our research on the acylation reactions [20][21][22][23], we wish to report here the synthesis of a series of new acylating reagents, which are useful for the chemoselective acylation of amino groups of compounds that possess both amino and other groups in water.…”

An environmentally friendly approach for the synthesis of quinazolinone sulfonamide

“…Meanwhile, some of their derivatives are used as antitumor chemotherapeutic agents [26][27][28][29][30]. On the other hand, one of its important derivatives contains sulfonamide functional groups which have been clinically used for many years, have been found to possess a large number of different biological activities [31][32][33][34][35][36], including anticonvulsant, anticancer, antifungal, antitumor, and antimicrobial activity [37][38][39][40][41].…”