1201938-10-4

Upstream product

• 3682-71-1 2-phenyl-2H-indazole 
• 108-37-2 1-bromo-3-chlorobenzene 
• 108-42-9 3-chloro-aniline 
• 586-96-9 Nitrosobenzene 
• 456-39-3 3-chlorobenzenediazonium tetrafluoroborate 
• 587-04-2 m-Chlorobenzaldehyde 
• 1227476-15-4 Azobenzene 

Relevant academic research and scientific papers

Continuous-Flow Visible Light Organophotocatalysis for Direct Arylation of 2H-Indazoles: Fast Access to Drug Molecules

A continuous-flow homogeneous photocatalytic method has been devised for the direct arylation of 2H-indazoles. This visible-light-promoted approach directly accesses a wide range of structurally diverse C3-arylated scaffolds of biological interest in a fa

Metal-free, regioselective, visible light activation of 4CzIPN for the arylation of 2H-indazole derivatives

Highly regioselective organo photocatalysis of 4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene) for the arylation of 2H-indazole is demonstrated. The present synthetic route provides a highly safe and easily accessible aniline precursor as an arylation reagent. The photoactivated 4CzIPN organocatalyst is found to be more efficient for single electron transfer without any organic base for the radical reaction. The carbazole-based photocatalyst (4CzIPN) with wide redox potential is stable and recyclable for further reaction transformations. Many indazole and aniline derivatives were used in the reaction and provided the arylated indazole derivatives in good to excellent yield.

Room-Temperature, Metal-Free, and One-Pot Preparation of 2H-Indazoles through a Mills Reaction and Cyclization Sequence

The Mills reaction and cyclization of readily available 2-aminobenzyl alcohols and nitrosobenzenes using thionyl bromide provided 2H-indazoles in up to 88 % yields. In the metal-free process, acetic acid played a crucial role for the both Mills reaction and cyclization. A brominated 2H-indazole could also be obtained through the one-pot sequence.

Cobalt(III)-catalyzed synthesis of indazoles and furans by C-H bond functionalization/addition/cyclization cascades

The development of operationally straightforward and cost-effective routes for the assembly of heterocycles from simple inputs is important for many scientific endeavors, including pharmaceutical, agrochemical, and materials research. In this article we describe the development of a new air-stable cationic Co(III) catalyst for convergent, one-step benchtop syntheses of N-aryl-2H-indazoles and furans by C-H bond additions to aldehydes followed by in situ cyclization and aromatization. Only a substoichiometric amount of AcOH is required as an additive that is both low-cost and convenient to handle. The syntheses of these heterocycles are the first examples of Co(III)-catalyzed additions to aldehydes, and reactions are demonstrated for a variety of aromatic, heteroaromatic, and aliphatic derivatives. The syntheses of both N-aryl-2H-indazoles and furans have been performed on 20 mmol scales and should be readily applicable to larger scales. The reported heterocycle syntheses also demonstrate the use of directing groups that have not previously been applied to Co(III)-catalyzed C-H bond functionalizations. Additionally, the synthesis of furans demonstrates the first example of Co(III)-catalyzed functionalization of alkenyl C-H bonds.

Direct arylations of 2H-Lndazoles on water

(Figure presented) The efficient palladium-catalyzed synthesis of a range of substituted 2H-lndazoles via C-H arylation Is reported. Reactions are performed on water and provide a direct and mild route toward 2,3-diaryl Indazoles of widespread biological significance.