49849-64-1

Upstream product

• 200125-70-8 (S)-2-methyl-1,2,3,4-tetrahydroquinoline 
• 98-59-9 p-toluenesulfonyl chloride 
• 1780-19-4 1,2,3,4-tetrahydro-2-methylquinoline 
• 59456-20-1 (rac)-(3-iodobutyl)benzeze 
• 70-55-3 toluene-4-sulfonamide 
• 2344-70-9 1-phenyl-3-butanol 
• 457622-20-7 4-(2-aminophenyl)-2-butanol 
• 953395-33-0 C₁₇H₂₁NO₃S 
• 953395-36-3 (+/-)-4-(2-(4-methylphenylsulfonamido)phenyl)-2-butyl 2-ethynylbenzoate 
• 953395-34-1 (+/-)-4-(2-(4-methylphenylsulfonamido)phenyl)-2-butyl 4-pentynoate 

Relevant academic research and scientific papers

Diboron-assisted palladium-catalyzed transfer hydrogenation of N-heteroaromatics with water as hydrogen donor and solvent

A Pd-catalyzed transfer hydrogenation of various N-heteroaromatic compounds with B2pin2 as a mediator and environmentally benign water as both solvent and hydrogen donor has been disclosed. This reaction proceeded under ambient temperature with a broad range of N-heteroaromatic compounds among which imidazo[1,2-a]pyridine derivatives were for the first time selectively reduced to 5,6,7,8-tetrahydroimidazo[1,2-a]pyridines, which are the core structural motifs of an inhibitor of human O-GlcNAcase. Mechanistic studies suggested that the new protons in products are from water and Pd-H might be the key intermediate with B2pin2 as the H2O activator.

Two-Step Protocol for Iodotrimethylsilane-Mediated Deoxy-Functionalization of Alcohols

We have developed a two-step protocol for iodotrimethylsilane-mediated deoxy-functionalization of primary and secondary alcohols to afford products containing a C?N, C?S, or C?O bond. In the first step the alcohol undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non-acidic pre-nucleophiles can be used, and the reaction proceeds with retention of configuration. This operationally simple, highly efficient protocol can be used for some natural products and small-molecule drugs containing hydroxy-group.

Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinolines

The synthesis and full 3D structural characterization of nine new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinoline derivatives are reported. These belong to a library whose rationale for the design was the previous knowledge of the biological relevant properties of both structural moieties. From protozoan antiparasitic screening, compounds 3 demonstrated interesting activity against Trypanozoma cruzi with low cytotoxicity. Besides, most compounds were moderately active against Plasmodium falciparum. Of these, 3 and 9 can be considered as lead scaffolds for further optimization. The substituent on BS did not influence the 3D structure properties and the 1H NMR spectra revealed the existence of an intramolecular weak hydrogen bond, C-H...O{double bond, long}S. Molecular modeling and X-ray crystallography also confirmed this finding, which is relevant to compound conformational preference.

Catalytic activation of the leaving group in the SN2 reaction

A novel catalytic activation of the leaving group in the SN2 reaction is achieved as an extension of our mercuric triflate-catalyzed reactions. Derivatives of anilinoethyl 4-pentynoate reacted smoothly with catalytic amounts of Hg(OTf)2 to give indoline derivatives in excellent yield with efficient catalytic turnovers under very mild conditions. The reaction of optically pure secondary alcohol derivatives resulted in inversion of stereochemistry, which is a definitive feature of the S N2 reaction. The procedure is applicable for benzoazepine synthesis.