An Efficient Synthesis of Sulfonylhydrazides and Sulfonylsemicarbazides by Utilizing Alumina as a Catalyst

Abstract

Sulfonyl hydrazides and sulfonyl semicarbazides are readily prepared by the reacting of hydrazine derivatives with sulfonyl chlorides in the presence of basic alumina under solvent‐free conditions. Reaction of a sulfonyl chloride with t‐butylcarbazate, followed by hydrolysis provides the corresponding sulfonyl hydrazides in higher yield and shorter time than previously reported.

Organic solvent-free synthesis of sulfonyl hydrazides in water

“…[5] Sulfonyl hydrazides were utilized as starting materials for palladium-catalyzed reductive homocoupling reaction synthesizing biaryl compounds, [6] iodine-mediated aryl transfer reaction, [7] palladium/copper-catalyzed arylation of alkenes, [8] hypervalent iodine (III)-promoted phenyl transfer reaction, [9] and palladiumcatalyzed regioselective C-2 arylation of benzofurans. [10] Previous synthesis of sulfonyl hydrazides including the reaction of sulfonyl chloride and hydrazine in suitable organic solvents with the presence of triethyl amine, [1] alumina as a catalyst, [11] and silica [12] Reactions in ionic liquid [13] and solvent free conditions under microwave irradiation [14] have also been reported. Furthermore, synthesis using copper-catalyzed cross-coupling of aryl halides with hydrazine in PEG-400, [15] microwave-assisted synthesis of sulfonamides directly from sulfonic acids, [16] and synthesis from thiols using H2O2-TAPC reagent system.…”

Synthesis,Characterization and Evaluation of Biological Activity of Sulfonylhydrazide-Schiff Base" (E)- N’-(2,5-dimethoxybenzalidene) naphthalene-2-sulfonohydrazide"

“…et al, 2019), which start by any group has sulfonyl chloride and hydrazine or amines, such reaction is carried out in a suitable solvent like: THF, DMSO and alcohols (Yang F-L. and Tian S-K., 2017;Senkal B.F. et al, 2001;Backes G.L. et al, 2014;Safaei-Ghomi J., 2007). Sulfonyl hydrazide is a starting point for many chemical reactions, which is considered as a crucial compounds in many fields of life such as medicine, some examples about these reaction are 3-sulfonyl nitrile and 3-Aryl benzofuran-thioether (Li W. et al, 2017 ;Zhao X. et al, 2015).…”

Synthesis,Characterization and Evaluation of Biological Activity of Sulfonylhydrazide-Schiff Base" (E)- N’-(2,5-dimethoxybenzalidene) naphthalene-2-sulfonohydrazide"

“…et al, 2019), which start by any group has sulfonyl chloride and hydrazine or amines, such reaction is carried out in a suitable solvent like: THF, DMSO and alcohols (Yang F-L. and Tian S-K., 2017;Senkal B.F. et al, 2001;Backes G.L. et al, 2014;Safaei-Ghomi J., 2007). Sulfonyl hydrazide is a starting point for many chemical reactions, which is considered as a crucial compounds in many fields of life such as medicine, some examples about these reaction are 3-sulfonyl nitrile and 3-Aryl benzofuran-thioether (Li W. et al, 2017 ;Zhao X. et al, 2015).…”