158293-42-6

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 622-58-2 p-Tolylisocyanate 
• 70-55-3 toluene-4-sulfonamide 

Downstream Products

• 1040402-89-8 N-p-tosyl-{2-[bis(2-methoxyethyl)amino]-6-methoxyphenyl}(2-thienyl)methylamine 
• 1040402-74-1 N-p-tosyl-{2-[bis(2-methoxyethyl)amino]-4,5-dimethylphenyl}(2-thienyl)methylamine 
• 1040402-79-6 N-p-tosyl-{2-[bis(2-methoxyethyl)amino]-3,6-dimethoxyphenyl}(2-thienyl)methylamine 
• 1040402-75-2 N-p-tosyl-{2-[bis(2-methoxyethyl)amino]-4,5-trimethylenephenyl}(2-thienyl)methylamine 
• 1040402-86-5 N-p-tosyl-{2-[bis(2-methoxyethyl)amino]-3-methylphenyl}(2-thienyl)methylamine 
• 1040402-88-7 N-p-tosyl-{2-[bis(2-methoxyethyl)amino]-6-methylphenyl}(2-thienyl)methylamine 
• 1040402-82-1 N-p-tosyl-{2-[bis(2-methoxyethyl)amino]-4-methoxyphenyl}(2-thienyl)methylamine 
• 1040402-81-0 N-p-tosyl-{2-[bis(2-methoxyethyl)amino]-5-methoxyphenyl}(2-thienyl)methylamine 
• 1040402-85-4 N-p-tosyl-{2-[bis(2-methoxyethyl)amino]-4-fluorophenyl}(2-thienyl)methylamine 
• 1040402-84-3 N-p-tosyl-{2-[bis(2-methoxyethyl)amino]-5-fluorophenyl}(2-thienyl)methylamine 
• 1040402-77-4 N-p-tosyl-{3-[bis(2-methoxyethyl)amino]naphthalen-2-yl}(2-thienyl)methylamine 
• 1040402-76-3 N-p-tosyl-{2-[bis(2-methoxyethyl)amino]-4,5-tetramethylenephenyl}(2-thienyl)methylamine 

Relevant academic research and scientific papers

The first enzyme-promoted addition of nitromethane to imines (aza-Henry reaction)

Enzyme catalytic promiscuity is the ability of a single enzyme active site to catalyze several chemical transformations, among them those which are different from natural. We have attempted to use this feature of enzymes in the nucleophilic addition of nitromethane to aldimines (the aza-Henry reaction) whose chemically catalyzed version leads to synthetically useful β-nitroamines. We succeded in obtaining for the first time the desired products in the yields up to 81%. The most efficient proved lipase TL (from Pseudomonas stutzeri) and oxynitrilase from Arabidopsis thaliana. However, all the reactions investigated were non-stereoselective.

Domino Synthesis of 3-Alkyliden-2,3-Dihydro-4-Quinolones

The synthesis of 3-alkyliden-2,3-dihydro-4-quinolones has been accomplished in a domino fashion through a three-step sequence that comprised an initial aza-Baylis-Hillman reaction, followed by a 1,3-rearrangement and an intramolecular amination. Starting from readily available aryl vinyl ketones and N-tosyl imines, the reaction with PPh3, CsOAc and CuI in CH3CN gave rise, in good overall yields, to final 3-alkyliden-4-quinolone derivatives, valuable scaffolds in medicinal chemistry. The simultaneous addition of two bases, PPh3 and CsOAc, was found to be crucial for the success of the process. While PPh3 promoted the reversible aza-Baylis-Hillman reaction, CsOAc triggered the subsequent 1,3-rearrangement, which shifted the initial equilibrium and allowed to complete the synthetic sequence upon the addition of CuI. (Figure presented.).

Silica-supported zinc chloride (ZnCl2/SiO2)-induced efficient protocol for the synthesis of N-sulfonyl imines and 2-Arylbenzothiazole

A straightforward strategy for the synthesis of N-sulfonyl imine derivatives from sulfonamides and aryl aldehydes utilizing Silica-supported zinc chloride (ZnCl2/SiO2, silzic) as a catalyst under solvent-free conditions has been developed. 2-Arylbenzothiazole derivatives were also synthesized by the reaction of 2-aminothiophenol with aryl aldehydes under the same conditions. This procedure has advantages of high yields, mild reaction condition, simple procedure, low cost, and simplicity of workup. The catalyst has the same efficiency on its reuse up to three times.

NHC ligand-enabled Ni-catalyzed reductive coupling of alkynes and imines using isopropanol as a reductant

A nickel-catalyzed reductive coupling of alkynes and imines using readily available isopropanol as the reducing agent was developed. The use of a sterically bulky and electron-rich carbene ligand (AnIPr) significantly promotes the reaction, providing various multi-substituted allylic amines in 23-89% yield and the corresponding chiral ligand (AnIPr-3) can afford the products in 51-95% ee.

Enantioselective Aza-Reformatsky Reaction with Ketimines

Here, an enantioselective aza-Reformatsky reaction using acyclic ketimine substrates is presented. Using α-phosphorated ketimines as electrophilic substrates and a simple BINOL-derived ligand, phosphorated analogues of aspartic acid holding chiral tetrasubstituted carbons are efficiently obtained with excellent enantioselectivity through an asymmetric organocatalytic Reformatsky-type reaction. The phosphorated analogues of aspartic acid have been used for the synthesis of phosphorus-containing enantiopure tetrasubstituted β-lactams.

Synthesis of novel N-(p-toluenesulfonyl)aminophosphonates and evaluation of their biological properties

The synthesis of a series of N-sulfonylaminophosphonates 2aA-2dC and evaluation of their cytotoxicity and ecotoxicity is described. N-sulfonylaminophsophonates 2aA-2dC were obtained by addition of dialkyl phosphites to azomethine bonds of sulfonimines 1a-

Synthesis of Benzyl Amines via Copper-Catalyzed Enantioselective Aza-Friedel-Crafts Addition of Phenols to N -Sulfonyl Aldimines

A new copper-catalyzed enantioselective aza-Freidel-Crafts reaction between phenols and N-sulfonyl aldimines that provides chiral secondary benzylamines in good to excellent yields and excellent enantioselectivities (up to 99% ee) is disclosed. In particular, excellent scope with alkylimines was observed for the first time. The synthetic utility of the products was demonstrated in the first enantioselective synthesis of a dual orexin receptor antagonist, a compound that contains an amine-bearing stereocenter adjacent to a bis-ortho-functionalized arene.

Asymmetric Arylation of Imines Catalyzed by Heterogeneous Chiral Rhodium Nanoparticles

Asymmetric arylation of aldimines catalyzed by heterogeneous chiral rhodium nanoparticles has been developed. The reaction proceeded in aqueous media without significant decomposition of the imines by hydrolysis to afford chiral (diarylmethyl)amines in high yields with outstanding enantioselectivities. This catalyst system exhibited the highest turnover number (700) in heterogeneous catalysts reported to date for these reactions. The reusability of the catalyst was also demonstrated.

Aza-Morita-Baylis-Hillman reactions catalyzed by a cyclopropenylidene

Catalysis using a bis(dialkylamino)cyclopropenylidene (BAC) has been developed, which relies on a formal umpolung activation of Michael acceptor pro-nucleophiles. Various aza-Morita-Baylis-Hillman reactions between aromatic, heteroaromatic, or aliphatic imines and acyclic or cyclic α,β-unsaturated ketones and carboxylic acid derivatives have been catalyzed by a BAC under mild conditions. Functionalities such as unprotected amino and hydroxy groups have been tolerated. The catalyst loading was decreased to 1 mol% without loss of activity. The BAC catalyst was shown to be substantially more active than a cyclic (alkyl)(amino) carbene (CAAC), N-heterocyclic carbenes (NHCs), and P- or N-centered Lewis bases.