3682-75-5

Usage

Compound Class

Indazole derivatives

Usage

Pharmaceutical research and development

Potential Applications

a. Inflammation treatment
b. Pain management
c. Cancer treatment

Unique Features

Structure and properties

Ongoing Research

Studies to explore full potential and possible medical applications

InChI:InChI=1/C14H12N2O/c1-17-13-8-6-12(7-9-13)16-10-11-4-2-3-5-14(11)15-16/h2-10H,1H3

Upstream product

• 151383-59-4 4-methoxy-N-(2-nitrobenzyl)benzenamine 
• 16035-87-3 N-(p-nitrobenzyl)-p-anisidine 
• 262364-63-6 N-(2-bromo-benzyl)-N-(4-methoxy-phenyl)hydrazine 
• 23308-83-0 (2-nitrobenzyl)triphenylphosphonium bromide 
• 5416-93-3 4-Methoxyphenyl isocyanate 
• 104-94-9 4-methoxy-aniline 
• 552-89-6 2-nitro-benzaldehyde 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 271-44-3 benzimidazole 
• 126275-49-8 [1-(2-Azido-phenyl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine 
• 16714-25-3 2-azidobenzaldehyde 
• 6630-33-7 ortho-bromobenzaldehyde 
• 89-98-5 2-chloro-benzaldehyde 

Downstream Products

• 40643-17-2 4-(2H-indazol-2-yl)phenol 
• 848142-60-9 4-(3-chloroindazol-2-yl)phenol 
• 1334951-11-9 2-(4-methoxyphenyl)-3-phenyl-2H-indazole 
• 1095510-29-4 3-benzyl-2-(4-methoxy-phenyl)-2H-indazole 

Relevant academic research and scientific papers

Synthesis of 2-aryl-2H-indazoles by base catalysed reaction of 2-nitrobenzyl triphenylphosphonium bromide and aryl isocyanates

The synthesis of a series of 2-aryl-2H-indazoles is reported. These compounds are obtained in moderate to good yield by reaction of 2-nitrobenzyl triphenylphosphonium bromide with aryl isocyanates, catalysed by sodium hydride or DBU. (C) 2000 Elsevier Science Ltd.

Synthesis, antiprotozoal activity, and cheminformatic analysis of 2-phenyl-2h-indazole derivatives

Indazole is an important scaffold in medicinal chemistry. At present, the progress on synthetic methodologies has allowed the preparation of several new indazole derivatives with interesting pharmacological properties. Particularly, the antiprotozoal activity of indazole derivatives have been recently reported. Herein, a series of 22 indazole derivatives was synthesized and studied as antiprotozoals. The 2-phenyl-2H-indazole scaffold was accessed by a one-pot procedure, which includes a combination of ultrasound synthesis under neat conditions as well as Cadogan’s cyclization. Moreover, some compounds were derivatized to have an appropriate set to provide structure-activity relationships (SAR) information. Whereas the antiprotozoal activity of six of these compounds against E. histolytica, G. intestinalis, and T. vaginalis had been previously reported, the activity of the additional 16 compounds was evaluated against these same protozoa. The biological assays revealed structural features that favor the antiprotozoal activity against the three protozoans tested, e.g., electron withdrawing groups at the 2-phenyl ring. It is important to mention that the indazole derivatives possess strong antiprotozoal activity and are also characterized by a continuous SAR.

Metal-free regioselective C-H amination for the synthesis of pyrazole-containing 2H-indazoles

A general and practical regioselective approach for the C-H amination of 2H-indazoles under transition-metal-free conditions was developed. A series of substrates were tested showing eminent functional group tolerance and affording the C-N functionalization products in good to excellent yields. Mechanism studies revealed that a radical process was involved in this transformation.

Manganese-Catalyzed Electrochemical Tandem Azidation-Coarctate Reaction: Easy Access to 2-Azo-benzonitriles

A one-pot cascade transformation consisting of an electrochemically driven azidation of 2H-indazole followed by coarctate fragmentation is developed to synthesize the 2-azo-benzonitrile motif. This manganese-catalyzed transformation is external-chemical-oxidant-free and operates at ambient temperature under air. This methodology exhibits good functional group tolerance, affording a broad range of substrate scopes of up to 89% isolated yield. Diverse derivatization of the 2-azo-benzonitrile product resulted in other valuable scaffolds.

Oxidative cross-dehydrogenative coupling (CDC)viaC(sp2)-H bond functionalization:tert-butyl peroxybenzoate (TBPB)-promoted regioselective direct C-3 acylation/benzoylation of 2H-indazoles with aldehydes/benzyl alcohols/styrenes

An efficient, cost-effective, transition-metal-free, oxidative C(sp2)-H/C(sp2)-H cross-dehydrogenative couplingviaa C(sp2)-H bond functionalization protocol for the regioselective direct C-3 acylation/benzoylation of subst

Direct Formation of 2-Substituted 2 H-Indazoles by a Pd-Catalyzed Reaction between 2-Halobenzyl Halides and Arylhydrazines

A direct and operationally simple method for the regioselective synthesis of 2-aryl-substituted 2H-indazoles is reported. The Pd-catalyzed reaction between easily available 2-bromobenzyl bromides and arylhydrazines employing Cs2CO3 as the base and t-Bu3PHBF4 as the ligand in DMSO at 120 °C in a sealed tube delivers the 2-substituted-2H-indazoles in a single synthetic step with yields up to 79%. The new method is based on a regioselective intermolecular N-benzylation followed by intramolecular N-arylation and oxidation.

Direct C3 Carbamoylation of 2H-Indazoles

We developed a novel method for direct C3 carbamoylation of 2H-indazoles using oxamic acids as carbamoyl radical sources. In the presence of ammonium persulfate, carbamoyl radicals were generated from oxamic acids, then used for further reactions with 2H-indazoles to afford the desired products. The reaction proceeds under metal- and catalyst-free conditions. This simple process allows for the efficient synthesis of C3 carbamoylated 2H-indazoles, which are important scaffolds in organic synthesis.

Tert-Butyl Hydroperoxide-Mediated Oxo-Sulfonylation of 2 H-Indazoles with Sulfinic Acid toward Indazol-3(2 H)-ones

A new and efficient oxo-sulfonylation protocol has been established for the synthesis of N-sulfonylated indazolones employing sulfinic acid as a sulfonylating agent using tert-butyl hydroperoxide (TBHP) under ambient air. A series of structurally diverse 1-sulfonylindazol-3(2H)-one derivatives were obtained in good yields. A radical reaction mechanism has been proposed for this transformation.

Bu4NI-catalyzed, oxidative C(sp2)-C(sp3)cross dehydrogenative coupling for the regioselective direct C-3 benzylation of 2: H -indazoles

A Bu4NI-catalyzed, DTBP-promoted, regioselective C(sp2)-C(sp3) cross dehydrogenative coupling (CDC) protocol for the direct C-3 benzylation of 2H-indazoles is reported. The metal-free protocol is operationally simple and proceeds mechanistically via the g

Synthesis method of 2H-indazole and derivatives thereof

The invention discloses a synthetic reaction of 2H-indazole and derivatives thereof under a metal-free condition. The new strategy has the advantages of no metal participation, wide substrate range and good functional group compatibility, and an efficient