Elemental Sulfur/DMSO‐Promoted Multicomponent One‐pot Synthesis of Malonic Acid Derivatives from Maleic Anhydride and Amines

Abstract

Malonic acid derivatives could be conveniently prepared with high degree of functional flexibility via redox condensation reactions between anhydride maleic, amines, elemental sulfur and DMSO as oxidant. This multicomponent decarboxylative transformation consists in a cascade of ring opening, decarboxylative oxidative thioamidation at temperature as low as 50 °C.magnified image

Recent Advances in the Synthesis of Heterocycles via Reactions Involving Elemental Sulfur

“…Monoamide of maleic acids 314 could involve in a decarboxylative coupling reaction with bis-nucleophiles 315 such as 2-aminophenol, o-phenylenediamine or 1,3-propanediamine promoted by sulfur/Nmethylpiperidine/DMSO to provide α-hetarylacetamides 316 (Scheme 112). [140] Such a decarboxylation was found to occur under mild condition of heating, which could be explained by the presence of the amide function of electron attracting nature. Interestingly, the starting substrates monoamide of maleic acids could be easily prepared in the same pot by spontaneous equimolar combination of amines 313 with cheap maleic anhydride.…”

Multicomponent synthesis of new 5‐thiourea‐4‐aza‐2,3 didehydropodophyllotoxins as potent cytotoxic agents

“…In another approach, they also synthesized malonic acid derivatives via redox condensation reactions between anhydride maleic, amines, elemental sulfur, and DMSO. This multicomponent reaction consists in a cascade of ring opening, decarboxylative oxidative thioamidation at ambient temperature [14]. Inspired by those researches, we aimed to investigate the synthesis of new podophyllotoxin compounds from the aniline derivatives 11 of 4‐aza‐2,3‐didehydropodophyllotoxin.…”

A reconfigurable crosslinking systemviaan asymmetric metal–ligand coordination strategy

“…Then we introduced these motifs into polymers and generated an M–L coordination crosslinked system through an one-pot multi-component polymerization according to previous work 52 (Fig. 1b).…”