Recent Advances in DMSO-Based Direct Synthesis of Heterocycles

Abstract

Besides serving as a low-toxicity, inexpensive and easily accessible solvent, dimethyl sulfoxide (DMSO) has also been extensively used as a versatile reagent for the synthesis of functionalized molecules. Dimethyl sulfoxide can not only be utilized as a carbon source, a sulfur source and an oxygen source, but also be employed as a crucial oxidant enabling various transformations. The past decade has witnessed a large number of impressive achievements on the direct synthesis of heterocycles as well as modifications of heterocyclic compounds by applying DMSO as a reagent. This review summarized the DMSO-based direct heterocycle constructions from 2012 to 2022.

Fluorinated Human Serum Albumin as Potential 19F Magnetic Resonance Imaging Probe

“…DMSO is an important solvent that dissolves both polar and nonpolar compounds and greatly increases the rate of nucleophilic substitution reactions. It exhibits several capabilities, such as high biocompatibility (nontoxic class 3 by the FDA), anti-inflammatory and bacteriostatic functions, and an antioxidant [ 71 , 72 ]. DMSO is widely used in life sciences and as an auxiliary solvent in the fabrication of polymers and drugs [ 73 ].…”

[DDQM][TFSI]: a room temperature ionic liquid as an active electrode material for supercapacitor devices and a catalyst for rapid synthesis of 4-aryl-NH-1,2,3-triazoles under microwave irradiation

“…16 The study was explored using DMSO as a solvent as it serves as a low-toxicity, inexpensive and easily accessible solvent. 17 The reaction was initially performed under microwave irradiation of 100 W from 150 1C to 200 1C for 10 minutes (Table S2, entries 2, 3 and 4, ESI †) but satisfactory yield of the desired product was not found. Afterwards the newly developed RTIL [DDQM][TFSI] was employed and a series of reactions were carried out with the variation of the catalyst loading, temperature and time, and to our delight, quantitative yields of the products were formed within 2 minutes upon application of an optimal microwave power of 90 W (180 1C) with 25 mol% of [DDQM][TFSI] as a catalyst and DMSO as the solvent (Table S2, entry 7, ESI †).…”

Recent advances in oxidative chlorination

“…DMSO has been frequently used not only as a synthon, but also as an oxidant in various transformations. 71 Xu and Hammond developed a novel 1,2-chlorothiolation of unactivated alkenes by the utilization of an HCl/DMPU/sulfoxide system in 2018 (Scheme 45). 72 A broad range of terminal and internal alkenes are tolerated in this system, affording the 1,2-difunctionalized products in moderate to excellent yields and with excellent regioselectivity (22 examples, 49–95% yield).…”