46479-70-3

Upstream product

• 63483-09-0 4-chloro-2-methyl-butanal 
• 35292-54-7 N-methyl-N-(p-methoxyphenyl)hydrazine 
• 2291-51-2 (5-methoxy-1,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-3-yl)acetonitrile 
• 110691-50-4 1,3-dimethyl-3-(2-aminoethyl)-5-methoxyoxindole 
• 109939-63-1 2-(2-(5-methoxy-1,3-dimethyl-2-oxoindolin-3-yl)ethyl)isoindoline-1,3-dione 
• 13888-03-4 methyl 4-chloro-2-methylbutanoate 
• 940-11-4 N-methyl-N-nitroso-p-anisidine 
• 5961-59-1 N-methyl-N-(4-methoxyphenyl)amine 

Downstream Products

• 2731-01-3 (±)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indole 
• 114546-56-4 (-)-N¹-phenethylnoreseromethole 
• 57-47-6 (+/-)-Physostigmine 

Relevant academic research and scientific papers

Reduction of Oxindoles with Sodium Bis(2-methoxyethoxy)aluminum Hydride, A Novel Reducing Agent

1,3-Dimethyl-3-(2'-dimethylaminoethyl)-5-tetrahydropyranyloxyoxindole (5), obtained on C3-alkylation of oxindole (4), was reduced stereoselectively with sodium bis(2-methoxyethoxy)aluminum hydride (Vitride) to carbinolamine (6).Oxindoles (7, 8, 9, 10 and

Decarboxylative Synthesis of Functionalized Oxindoles via An Iron-Initiated Radical Chain Process and Application in Constructing Diverse Fused-Indoline Heterocycles

Rapid construction of diverse fused-indoline?heterocycle (FIH) frameworks including high-value pyrroloindolines, furoindolines and thienoindolines in a two-step sequence has been described. The key to success hinges on the adoption of peresters as α-heteroatom alkyl radical precusors, which can smoothly react with N-arylacrylamides via a radical chain process initiated by inexpensive FeCl2?4H2O to afford the functionalized oxindoles, the key intermediates to FIH skeletons. The approach features operationally-simplicity, broad substrates scope and mild conditions. (Figure presented.).

A novel one-pot approach of hexahydropyrrolo[2,3-b ]indole nucleus by a cascade addition/cyclization strategy: Synthesis of (±)-esermethole

A practical and efficient synthesis of 3-substituted hexahydropyrrolo[2,3- b]indole is described. The addition/cyclization of 3-substituted indoles with α,β-dehydroamino esters in the presence of a Lewis acid provides hexahydropyrrolo[2,3-b]indole adducts in good yields and stereoselectivities. This approach has been applied to the concise synthesis of esermethole employing an appropriately substituted indole and an N-acyl dehydroamino ester.

Palladium-catalyzed enantioselective domino heck-cyanation sequence: Development and application to the total synthesis of esermethole and physostigmine

An efficient synthesis of functionalized 3-alkyl-3-cyanomethyl-2-oxindole 1 by a palladium-catalyzed domino Heck-cyanation reaction has been developed. Reaction of ortho-iodoanilide 5 with potassium ferro(II)cyanide, K 4[Fe(CN)6], dissolved in DMF in the presence of palladium acetate and sodium carbonate afforded oxindole 1 in good to excellent yields. An enantioselective domino Heck-cyanation process has been developed for the first time using (S)-DIFLUORPHOS as a chiral supporting ligand, and an enantioselectivity of up to 79% ee in the enantiomerically enriched oxindole was obtained under optimized conditions. A concise total synthesis of esermethole and physostigmine, powerful inhibitors of acetyl- and butyryl-cholinesterase, is documented.

Simple synthesis of racemic pyrrolo[2,3-b]indoles: Formal total synthesis of (±)-physostigmine

Racemic pyrrolo [2,3-b]indoles were efficiently synthesized by the reaction of aromatic hydrazines with 4-chloro-2-methylbutanal. A formal total synthesis of physostigmine was achieved.