503544-97-6

Upstream product

• 52191-26-1 2-chloro-N-<2-(indol-3-yl)ethyl>acetamide 
• 657-84-1 sodium tosylate 
• 61-54-1 tryptamine 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 473893-99-1 1-{2-(1H-benzo[b]azol-3-yl)ethyl}-3-(4-methylphenylsulfonyl)-2,6-azinanedione 
• 639007-41-3 3-ethylidene-1-[2-(1H-indol-3-yl)-ethyl]-5-(toluene-4-sulfonyl)-piperidine-2,6-dione 
• 640722-80-1 3-ethyl-1-[2-(1H-indol-3-yl)ethyl]-5-(toluene-4-sulfonyl)piperidine-2,6-dione 
• 639007-51-5 5-ethyl-1-[2-(1H-indol-3-yl)ethyl]-3-(toluene-4-sulfonyl)piperidin-2-one 
• 56491-03-3 (+/-)-deplancheine 

Relevant academic research and scientific papers

Synthesis of fused bicyclic glutarimides

We describe an efficient route towards the synthesis of fused bicyclic glutarimides using facile [3+3] reaction of α-sulfonylacetamides with different α,β-unsaturated esters as the key step. Intramolecular cyclization of 4-substituted 3-sulfonylglutarimide to form 5,6-, 6,6- or 6,7-fused bicyclic glutarimides was accomplished via alkylation, oxidative cyclization or ring-closing metathesis in modest yield.

Regioselective reduction of N-alkyl-3-sulfonylglutarimide. Formal synthesis of 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine and homobaclofen

Reduction of N-alkyl-3-sulfonylglutarimides with (1) sodium hydride and then with lithium aluminum hydride, or (2) sodium borohydride yielded two different types of regioselectively reduced hydroxypiperidinones which were further dehydrated to two pyridin-2-ones in the presence of boron trifluoride etherate. Cycloaddition and regioselective reduction were combined to synthesize 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine and homobaclofen.

An efficient synthesis of N-alkyl-4-substituted 3H-pyridine-2,6-dione. Synthesis of isoguvacine and MDL-11,939

An efficient route towards the synthesis of N-alkyl-4-substituted 3H-pyridine-2,6-dione using various N-alkyl-α-sulfonylacetamides and two α,β-unsaturated esters as starting materials is described. Isoguvacine and MDL-11,939 with have potential biological activities were synthesized via this strategy.

Reaction of different α-sulfonyl acetamides with methyl acrylate

The base-induced tandem-coupling/cyclization reactions of various α-sulfonyl acetamide derivatives A with methyl acrylate differentiated between two different pathways to form α-sulfonyl analogs of glutarimides B and 2-hydroxycyclohexenecarboxylic acid derivatives C in different ratios. The reaction of α-sulfonyl acetamide dianion with methyl acrylate depended on three factors: the stability of the dianion, concentration of methyl acrylate and the structure of sufonyl and amide substituents. By changing the reaction conditions, we efficiently controlled the cycloaddition reaction to synthesize the desired product, each of which has potential biological activities. A ring closure mechanism is proposed for the reactions.