News Update on Sulfonyl Research: Sep – 2019

News Update on Sulfonyl Research: Sep – 2019

News Update on Sulfonyl Research: Sep – 2019

An Efficient, Inexpensive, and Shelf-Stable Diazotransfer Reagent:  Imidazole-1-sulfonyl Azide Hydrochloride

The design and synthesis of a brand new diazotransfer chemical agent, imidazole-1-sulfonyl chemical compound complex, area unit rumored. This chemical agent has evidenced to equal triflyl chemical compound in its ability to act as a “diazo donor” within the conversion of each primary amines into azides and activated methylene radical substrates into cation compounds. Crucially, this chemical agent may be ready in a very one-pot reaction on an oversized scale from cheap materials, is shelf-stable, and is handily crystalline. [1]

Iodine‐Catalyzed Regioselective Sulfenylation of Indoles with Sulfonyl Hydrazides

New S in town: Sulfonyl hydrazides swimmingly bear sulfenylation with indoles within the presence of ten mol % I2 to grant structurally various indole thioethers in moderate to glorious yields with extraordinarily high regioselectivity. This study paves the method for the employment of sulfonyl hydrazides as distinctive sulfur electrophiles in chemical synthesis. [2]

[83] Sulfonylation with sulfonyl halides

This chapter describes the mechanism of sulfonylation with sulfonyl halides. Sulfonyl halides react with several of the aminoalkanoic acid esterases like chymotrypsin, trypsin, and acetylcholinesterase to sulfonylate the group of a particular aminoalkanoic acid residue within the site and thereby inhibit enzymic activity. Sulfonyl salts show nice variations in reactivity relying upon the catalyst and also the structure of the sulfonyl halide. The sulfonylated enzymes have chemical properties completely different from those of the corresponding phosphoryl enzymes attributable to the special chemical characteristics of salt esters. [3]

A rapid access to aliphatic sulfonyl fluorides

The past few years have witnessed a invasive analysis interest on the study of sulfonyl fluorides as reactive probes in chemical biology and molecular medical specialty, that raises Associate in Nursing pressing want for the event of effective artificial ways to expand the toolkit. Herein, we have a tendency to gift the invention of a facile and general approach for the synthesis of acyclic  sulfonyl fluorides via visible-light-mediated decarboxylative fluorosulfonylethylation. the tactic relies on plenteous acid feed stock, applicable to numerous group radical acids as well as primary, secondary, and tertiary acids, and is additionally appropriate for the modification of natural product like amino acids, peptides, further as medicine, formation a fast, metal-free approach to create sulfonyl halide compound libraries of extensive structural diversity. [4]

Simple Synthesis of Sulfonyl Amidine-Containing Glucosidase Inhibitors by a Chemoselective Coupling Reaction Between D-Gluconothiolactam and Sulfonyl Azides

In this report, we tend to describe an easy synthesis of gluconoamidinylsulfones as a brand new category of potential inhibitors toward glycan process enzymes. Gluconoamidinylsulfones have a glucose-based sulfonyl amidine skeleton, therefore would type a distorted half-chair conformation with charge, that is analogous to transition state within the accelerator method. A chemoselective coupling reaction between thioamide and sulfonyl compound enabled ballroom dancing synthesis of the iminosugar derivatives from commercially obtainable D-gluconothiolactam in an exceedingly protection-free manner. [5]

Reference

[1] Goddard-Borger, E.D. and Stick, R.V., 2007. An efficient, inexpensive, and shelf-stable diazotransfer reagent: imidazole-1-sulfonyl azide hydrochloride. Organic letters, 9(19), (Web Link)

[2] Yang, F.L. and Tian, S.K., 2013. Iodine‐Catalyzed Regioselective Sulfenylation of Indoles with Sulfonyl Hydrazides. Angewandte Chemie International Edition, 52(18), (Web Link)

[3] Gold, A.M., 1967. [83] Sulfonylation with sulfonyl halides. In Methods in enzymology (Vol. 11, pp. 706-711). Academic Press. (Web Link)

[4] A rapid access to aliphatic sulfonyl fluorides
Ruting Xu, Tianxiao Xu, Mingcheng Yang, Tianpeng Cao & Saihu Liao
Nature Communicationsvolume 10, Article number: 3752 (2019) (Web Link)

[5] Aswad, M., Chiba, J., Tomohiro, T. and Hatanaka, Y. (2017) “Simple Synthesis of Sulfonyl Amidine-Containing Glucosidase Inhibitors by a Chemoselective Coupling Reaction Between D-Gluconothiolactam and Sulfonyl Azides”, International Research Journal of Pure and Applied Chemistry, 14(2), (Web Link)

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