69558-74-3

Upstream product

• 6341-92-0 6-chloroisatin 

Downstream Products

• 1609644-91-8 1-benzyl-6-chloro-3-p-tolylindolin-2-one 
• 1446104-62-6 6-chloro-N-benzyl-2-oxo-3-diazoindole 

Relevant academic research and scientific papers

Facile synthesis of 3-aryloxindoles via Bronsted acid catalyzed friedel-crafts alkylation of electron-rich arenes with 3-diazooxindoles

A simple metal-free method for the synthesis of 3-aryloxindoles via Bronsted acid catalyzed aromatic C-H functionalization of electron-rich arenes with 3-diazooxindoles is developed. In the presence of a catalytic amount of TfOH, a series of 3-aryloxindoles are synthesized as single regioisomers in good to excellent yields. This transformation is proposed to proceed through acid-catalyzed protonation of 3-diazooxindoles into diazonium ions followed by Friedel-Crafts-type alkylation of arenes.

Synthesis of (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2Hindol-2-ones using an Eschenmoser coupling reaction

A highly modular method for the synthesis of (Z)-3-[amino(phenyl/methyl)methylidene]-1,3-dihydro-2H-indol-2-ones starting from easily available 3-bromooxindoles or (2-oxoindolin-3-yl)triflate and thioacetamides or thiobenzamides is described. A series of 49 compounds, several of which have previously been shown to possess significant tyrosin kinase inhibiting activity, was prepared in yields varying mostly from 70 to 97% and always surpassing those obtained by other published methods. The method includes an Eschenmoser coupling reaction, which is very feasible (even without using a thiophile except tertiary amides) and scalable. The (Z)configuration of all products was confirmed by NMR techniques.

Visible-Light-Mediated Cyclopropanation Reactions of 3-Diazooxindoles with Arenes

The cyclopropanation reaction of 3-diazooxindoles with arenes was first accomplished using visible-light irradiation. A series of spiro[norcaradiene-7,3′-indolin]-2′-ones were synthesized for the first time in high yields and with excellent diastereoselectivities. The synthetic usefulness of this catalyst-free photochemical methodology is illustrated by the further controllable rearrangement and epoxidation reactions.

Gold(I)-Catalyzed Dimerization of 3-Diazooxindoles towards Isoindigos

A gold-catalyzed dimerization of 3-diazooxindoles was developed, delivering isoindigos as products. The reaction shows broad substrate scope and functional group tolerance by affording various substituted isoindigos. Moreover, the method also exhibited high efficiency on a gram-scale reaction.

1-Substituted pyrazolo[1,5-c]quinazolines as novel Gly/NMDA receptor antagonists: Synthesis, biological evaluation, and molecular modeling study

A new set of 5,6-dihydro-pyrazolo[1,5-c]quinazoline-2-carboxylates (2-18), bearing different substituents (COOEt, Cl, Br, CH3, and COOH) at position-1, were synthesized in order to investigate the influence of various groups at this specific position on Gly/NMDA receptor affinity and/or selectivity. All the herein reported compounds were evaluated for their binding at the Gly/NMDA, AMPA, and KA receptors. Some selected compounds were also tested for their functional antagonistic activity at both the AMPA and NMDA receptor-ion channels. The results obtained in this study have highlighted that a C-1 lipophilic substituent on the pyrazolo[1,5-c]quinazoline-2-carboxylate core shifts selectivity toward the Gly/NMDA receptor, while a C-1 anionic carboxylate residue is able to increase affinity toward this receptor subtype. In particular, the 2-carboxylic acids 15 and 16, bearing a chlorine atom at position-1, are not only potent (Ki = 0.18 and 0.16 μM, respectively), but also highly Gly/NMDA versus AMPA selective (selectivity ratio > 500). Furthermore, the 1,2-dicarboxylic acids 13 and 14 are endowed with the highest Gly/NMDA receptor binding activity (Ki = 0.09 and 0.059 μM, respectively), among the pyrazoloquinazoline series of derivatives. A molecular modeling study has been carried out to better understand receptor affinity and selectivity of these new pyrazoloquinazoline derivatives.