Multicomponent synthesis of biologically relevant S-benzyl dithiocarbamates from para-quinone methides, amines, and carbon disulfide are described under catalyst and additive-free conditions. The reactions proceeded at room temperature in a short span of time with excellent yields. One of the synthesized compounds, 3e showed considerable acetylcholinesterase (AChE) inhibitory (51.70 + 5.63% at 20 μm) and antioxidant (63.52 ± 1.15 at 20 μm) activities.Article pubs.acs.org/joc

The palladium-catalyzed one-pot synthesis of 2,3-deoxy-3-keto aryl C-glycosides is achieved from glycals and anilines in the presence of tert-butyl nitrite and aqueous HBF4 under mild conditions. This one-pot method stereospecifically provides α- and β-aryl glycosides (≥19:1 by NMR) in good yields at room temperature. The configuration at the C-3 position in the glycal determines the anomeric selectivity (i.e., α or β) of the desired products.

Preparation of S-aryl thioglycosides from 1-thiosugars via S-arylation was demonstrated under mild reaction conditions. A wide range of protected and unprotected 1-thiosugars derived from glucose, glucosamine, galactose, mannose, ribose, maltose, and lactose underwent cross-coupling reactions with functionalized aryldiazonium salts in the presence of copper­(I) chloride and DBU. The desired products were obtained in 55–88% yields within 5 min. Various functional groups, including halogens, were tolerated under standard reaction conditions. Synthesis of the biologically relevant antidiabetic dapagliflozin S-analogue and arbutin S-analogues (tyrosinase inhibitors) was demonstrated.

An efficient approach for the preparation of C‐1 aryl enones from aryl iodides and glycal enones by palladium‐catalyzed cross‐coupling reactions under ligand‐free conditions was developed. A wide range of aryl iodides bearing electron‐donating and withdrawing groups underwent oxidative C‐1 arylation with galactal, glucal and rhamnal enones in the presence of Pd(OAc)2 and AgNO3 under mild conditions. The protecting groups, including benzyl, acetyl, pivaloyl, and benzoyl groups, were found to be compatible under standard reaction conditions. The developed methodology was applied for the preparation of dapagliflozin analogues (SGLT‐2 inhibitors). Regioselective nitration of C‐1 aryl enones provides C‐2 nitro aryl enones in good yields.

Triflic acid promoted multi-component synthesis of functionalized S-benzyl dithiocarbamates from diazo compounds, carbon disulfide and secondary amines is reported. The reactions proceeded at room temperature and gave the desired dithiocarbamates...