18152-60-8

Upstream product

• 13888-03-4 methyl 4-chloro-2-methylbutanoate 
• 24438-17-3 1,3-dimethylindolin-2-one 
• 1949-57-1 2-(2-Bromo-phenyl)-N-methyl-propionamide 
• 98192-14-4 2-bromo-N-methylbenzenesulfonamide 
• 2905-25-1 o-bromobenzenesulfonyl chloride 
• 154386-63-7 N-(2-iodophenyl)-N-methylmethacrylamide 
• 108501-85-5 N-(2-iodophenyl)-2-methylacrylamide 
• 615-43-0 2-iodophenylamine 
• 176327-11-0 (1,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-3-yl)acetonitrile 
• 633337-26-5 N-[2,3-dihydro-1,3-dimethyl-3-(prop-2-enyl)-3H-indole-2-ylidene]acetamide 
• 633337-23-2 2,3-dihydro-2-imino-1,3-dimethyl-3-(prop-2-enyl)-3H-indole hydrate 
• 633337-25-4 2,3-dihydro-1,3-dimethyl-3-(prop-2-enyl)-3H-indole-2-one 
• 633337-28-7 3-(3,3-diethoxypropyl)-2,3-dihydro-1,3-dimethyl-1H-indol-2-one 
• 633337-27-6 2,3-dihydro-1,3-dimethyl-2-oxo-1H-indol-3-acetaldehyde 

Relevant academic research and scientific papers

Cobalt-Catalyzed 1,4-Aryl Migration/Desulfonylation Cascade: Synthesis of α-Aryl Amides

A cobalt-catalyzed 1,4-aryl migration/disulfonylation cascade applied to α-bromo N-sulfonyl amides was developed. The reaction was highly chemoselective, allowing the preparation of α-aryl amides possessing a variety of functional groups. The method was used as the key step to synthesize an alkaloid, (±)-deoxyeseroline. Mechanistic investigations suggest a radical process.

Synthesis and cytotoxic activity of novel hexahydropyrrolo[2,3-b]indole imidazolium salts

A series of novel hexahydropyrrolo[2,3-b]indole-1H-imidazolium salts were synthesized and evaluated in vitro against a panel of human tumor cell lines. The results suggest that the 5,6-dimethyl-benzimidazole ring, and substitution of the imidazolyl-3-posi

Exploration of the interrupted Fischer indolization reaction

A convergent method to access the fused indoline ring system present in a multitude of bioactive molecules has been developed. The strategy involves the condensation of hydrazines with latent aldehydes to ultimately deliver indoline-containing products by way of an interrupted Fischer indolization sequence. The method is convergent, mild, operationally simple, broad in scope, and can be used to access enantioenriched products. In addition, our approach is amenable to the synthesis of furoindoline and pyrrolidinoindoline natural products as demonstrated by the concise formal total syntheses of physovenine and debromoflustramine B. The strategy will likely enable the synthesis of more complex targets such as the communesin alkaloids.

Synthesis and biological evaluation of (-)- and (+)-debromoflustramine B and its analogues as selective butyrylcholinesterase inhibitors

A series of pyrrolidinoindolines have been synthesized as debromoflustramine B (4a) analogues for their evaluation as cholinesterase inhibitors. Structure-activity studies of this series revealed the optimum pharmacophore elements required for activity and resulted in the discovery of selective butyrylcholinesterase inhibitors with micromolar potency. Biological testing demonstrated that (-)-4a was 7500 times more potent than its enantiomer (+)-4b. The most active inhibitor against BChE in the series was demethyldebromoflustramine B (5a), with an IC50 value of 0.26 μM. X-ray crystallography of 15 and docking studies of selected compounds into human BChE (PDB 1POI) are presented. Molecular modeling studies showed that π-hydrogen bond, classical hydrogen bond, and cation-π interactions are critical for optimum potency.

Intramolecular cyanoamidation of unsaturated cyanoformamides catalyzed by palladium: an efficient synthesis of multi-functionalized lactams

The Pd(0)-catalyzed intramolecular cyanoamidation of several unsaturated cyanoformamides with alkenyl, allenyl, and alkynyl groups was investigated. In the cases of alkynyl and 1,1-disubstituted alkenyl cyanoformamides, the Pd(0)-catalyzed C-CN activation and subsequent insertion reaction proceeded smoothly and gave the corresponding lactams bearing a cyano group at the β-position in good yields. The mechanism of the reaction was also discussed.

A novel synthetic approach to (±)-desoxynoreseroline

(±)-Desoxynoreseroline (3), the basic ring structure of the pharmacologically active alkaloid physostigmine (1), was synthesized starting from 3-allyl-1,3-dimethyloxindole (9). The latter was prepared from the corresponding 2H-azirin-3-amine 6 by a BFsub

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.