29475-88-5

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 6218, 1995 DOI: 10.1021/jo00124a048

InChI:InChI=1/C16H13N/c1-2-6-13(7-3-1)10-11-15-12-14-8-4-5-9-16(14)17-15/h1-12,17H/b11-10+

Upstream product

• 2515-46-0 3-methyl-1,5-diphenyl-4,5-dihydro-1H-pyrazole 
• 100-52-7 benzaldehyde 
• 144137-01-9 (1-methoxycarbonylindol-2-yl)methyl(triphenyl)phosphonium bromide 
• 100-63-0 phenylhydrazine 
• 1896-62-4 (E)-benzalacetone 
• 201230-82-2 carbon monoxide 
• 7654-06-0 3-phenyl-2H-azirine 
• 124643-50-1 (E)-2-(4-phenylbut-3-en-1-yn-1-yl)aniline 
• 95-20-5 2-methyl-1H-indole 
• 143952-53-8 methyl 2-methyl-1H-indole-1-carboxylate 
• 78133-84-3 (2-aminobenzyl)triphenylphosphonium bromide 
• 102-92-1 Cinnamoyl chloride 
• 1190425-92-3 (E)-N-(2-pyridylsulfonyl)-2-styrylindole 
• 19005-93-7 1H-indol-2-ylcarboxaldehyde 

Downstream Products

• 136558-72-0 2-Phenyl-3,3,4,4-tetracyano-1,2,3,4-tetrahydro-9H-carbazole 
• 121897-57-2 methyl 2β-phenyl-1,2,3,4-tetrahydro-9H-carbazole-3β-carboxylate 
• 136558-68-4 dimethyl 2-phenyl-1,2-dihydro-9H-carbazole-3,4-dicarboxylate 
• 134924-10-0 5-phenyl-1,4-dihydro-7H-benzocarbazol-1,4-dion 

Relevant academic research and scientific papers

Nickel-Catalyzed Straightforward and Regioselective C-H Alkenylation of Indoles with Alkenyl Bromides: Scope and Mechanistic Aspect

Nickel-catalyzed regioselective C-H bond alkenylation of indoles and related heteroarenes with alkenyl bromides is accomplished under relatively mild conditions. This method allows the straightforward synthesis of C-2 alkenylated indoles employing an air-stable and well-defined nickel catalyst, (bpy)NiBr2, providing a solution to the limitations associated with hydroindolation and oxidative alkenylation. The reaction conceded the coupling of indole derivatives with various alkenyl bromides, such as aromatic and heteroaromatics, α- and β-substituted as well as exo- and endo-cyclic alkenyl compounds. An extensive mechanistic investigation, including controlled study, reactivity experiments, kinetics and labeling studies, and EPR and XPS analyses, highlights that the alkenylation proceeds through a single-electron transfer process comprising an odd-electron oxidative addition of alkenyl bromide. Furthermore, the alkenylation operates via a probable Ni(I)/Ni(III) pathway involving the rate-limiting C-H nickelation of indole.

Organocatalytic diels-alder reaction of 2-vinylindoles with methyleneindolinones: An efficient approach to functionalized carbazolespirooxindoles

An unprecedented asymmetric Diels-Alder reaction of 2-vinylindoles with methyleneindolinones has been disclosed. Under bifunctional organocatalysis by cinchona-derived squaramide catalyst, a series of diversely functionalized carbazolespirooxindole derivatives bearing three contiguous stereocenters are rapidly constructed under mild conditions (48-90% yields, up to >20:1 dr and 99% ee).

Rhodium-Catalyzed Aryl Migratory/Decarbonylation of Diaryl Ketones via the Activation of Unstrained C-C Bonds

A Rh-catalyzed aryl migratory/decarbonylation of unstrained ketones has been developed. This viable transformation provides a complementary decarbonylative method using diaryl ketones to afford a variety of alkenylated heterocycles in good yields with moderate to good stereoselectivity and broad substrate scope. The synthetic utility of this protocol is also demonstrated by the conversion of the alkenylated heterocycles to tetrahydrocarbazole derivatives.

One-Pot Reaction between N-Tosylhydrazones and 2-Nitrobenzyl Bromide: Route to NH-Free C2-Arylindoles

A one-pot Barluenga coupling between N-tosylhydrazones and nitro-benzyl bromide, followed by deoxygenation of ortho-nitrostyrenes, and subsequent cyclization has been developed, providing a new way to synthesize various C2-arylindoles. This method exhibits a good substrate scope and functional group tolerance, and it allows an access to NH-free indoles, which can present a potential utility in medicinal chemistry applications.

Cobalt(III)?Catalyzed C?H Activation: A Secondary Amide Directed Decarboxylative Functionalization of Alkynyl Carboxylic Acids Wherein Amide NH-group Remains Unreactive

A Co(III)-catalyzed C?H activation reaction for ortho-alkenylation of benzamides (aryl/heteroaryl) and C2-alkenylation of indole derivatives have been developed using alkynyl carboxylic acid as an alkene source. A high regioselectivity has been achieved i

Benzannulation of 2-Alkenylindoles using Aldehydes by Sequential Triple-Relay Catalysis: A Route to Carbazoles and Carbazole Alkaloids

Benzannulation of 2-alkenylindoles with readily available aldehydes, under one-pot sequential triple-relay-catalysis, provides an easy access to several structurally unique carbazoles including 2- and 3-alkenylcarbazoles. This protecting group-free method enabled one-pot synthesis of alkaloids such as hyellazole and 6-chlorohyellazole, and the formal syntheses of seven other alkaloids. Construction of the core structure, present in murastifoline A, murrafoline E, and related alkaloids was also demonstrated. Even conjugated 3,3′-biscarbazoles can also be synthesized by one-pot, two-fold sequential triple-relay catalysis. (Figure presented.).

A Scalable Method for Regioselective 3-Acylation of 2-Substituted Indoles under Basic Conditions

Privileged structures such as 2-arylindoles are recurrent molecular scaffolds in bioactive molecules. We here present an operationally simple, high yielding and scalable method for regioselective 3-acylation of 2-substituted indoles under basic conditions

Palladium-catalyzed α-arylation of enones in the synthesis of 2-alkenylindoles and carbazoles

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Rh(i)-catalyzed decarbonylative direct C2-olefination of indoles with vinyl carboxylic acids

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