753451-40-0

Upstream product

• 154867-50-2 N-(2-iodophenyl)propiolamide 
• 620-05-3 iodomethylbenzene 
• 615-43-0 2-iodophenylamine 

Downstream Products

• 753451-34-2 (E)-1-benzyl-3-pentylideneindolin-2-one 
• 71687-76-8 (E)-1-benzyl-3-benzylidene-1,3-dihydro-indol-2-one 
• 343830-62-6 1-benzyl-(Z)-3-(benzylidene)indolin-2-one 
• 1383675-34-0 1,5-dibenzyl-1H-[1,2,3]triazolo[4,5-c]quinolin-4(5H)-one 
• 18217-64-6 (E)-1-benzyl-3-(methoxycarbonyl)methylene-1,3-dihydroindol-2-one 

Relevant academic research and scientific papers

Synthesis of (E)-oxindolylidene acetate using tandem palladium-catalyzed Heck and alkoxycarbonylation reactions

Tandem reactions use consecutive reaction steps to efficiently synthesize compounds of high molecular complexity. This paper presents a tandem Pd-catalyzed Heck and alkoxycarbonylation reaction for the stereoselective synthesis of (E)-oxindolylidene acetates. The mechanism underlying the Pd-catalyzed tandem reaction involves the syn-carbopalladation of ynamides followed by alkoxycarbonylation with CO and alcohol. This method makes it possible to obtain the desired (E)-configuration of oxindolylidene acetates exclusively. We evaluated the scope of the reaction by applying optimal reaction conditions to the facile synthesis of a library of (E)-oxindolylidene acetates. The resulting (E)-oxindolylidene acetates exhibited potent anticancer activities against a variety of human cancer cell lines. The anticancer activities of some (E)-oxindolylidene acetates were even superior to those of known CDK inhibitors indirubin-3′-oxime and roscovitine.

A CuAAC/Ullmann C-C coupling tandem reaction: Copper-catalyzed reactions of organic azides with N -(2-Iodoaryl)propiolamides or 2-iodo- N -(prop-2-ynyl)benzenamines

A novel copper-catalyzed tandem reaction was developed by utilizing two famous copper-catalyzed reactions, CuAAC and Ullmann coupling. The trapping of the C-Cu intermediate produced in CuAAC led to further formation of an aryl C-C bond through intramolecu

Synthesis and structure-activity relationships of constrained heterocyclic analogues of combretastatin A4

A series of combretastatin A4 (CA4) analogues with a lactam or lactone ring fused to the trimethoxyphenyl or the B-phenyl moiety were synthesized in an efficient and stereoselective manner by using a domino Heck-Suzuki-Miyaura coupling reaction. The vascular-disrupting potential of these conformationally restricted CA4 analogues was assessed by various invitro assays: inhibition of tubulin polymerization, modification of endothelial cell morphology, and disruption of endothelial cell cords. Compounds were also evaluated for their growth inhibitory effects against murine and human tumor cells. B-ring-constrained derivatives that contain an oxindole ring (in contrast to compounds with a benzofuranone ring) as well as analogues bearing a six-membered lactone core fused to the trimethoxyphenyl ring are endowed with significant biological activity. The most potent compound of this series (oxindole 9b) is of particular interest, as it combines chemical stability and a biological activity profile characteristic of a vascular-disrupting agent.

Tandem Heck-Suzuki-Miyaura reaction: Application to the synthesis of constrained analogues of combretastatin A-4

A series of compounds related to combretastatin A-4 has been synthesized by a tandem Heck-carbocyclization/Suzuki coupling process. From various alkynamides and 3,4,5-trimethoxyphenyl boronic acid or the corresponding styryl derivative, (E)-3-arylmethylen