69913-80-0

Upstream product

• 33439-27-9 N-tosyl-4-piperidone 
• 59-88-1 phenylhydrazine hydrochloride 
• 41661-47-6 piperidin-4-one 
• 98-59-9 p-toluenesulfonyl chloride 
• 1227476-15-4 Azobenzene 
• 100-63-0 phenylhydrazine 

Downstream Products

• 1268694-36-5 1-tosyl-2,3-dihydro-1H-pyrrolo[3,2-b]quinolin-9(4H)-one 

Relevant academic research and scientific papers

Direct Synthesis of Indoles from Azoarenes and Ketones with Bis(neopentylglycolato)diboron Using 4,4′-Bipyridyl as an Organocatalyst

Multifunctionalized indole derivatives were prepared by reducing azoarenes in the presence of ketones and bis(neopentylglycolato)diboron (B2nep2) with a catalytic amount of 4,4′-bipyridyl under neutral reaction conditions, where 4,4′-bipyridyl acted as an organocatalyst to activate the B-B bond of B2nep2 and form N,N′-diboryl-1,2-diarylhydrazines as key intermediates. Further reaction of N,N′-diboryl-1,2-diarylhydrazines with ketones afforded N-vinyl-1,2-diarylhydrazines, which rearranged to the corresponding indoles via the Fischer indole mechanism. This organocatalytic system was applied to diverse alkyl cyclic ketones, dialkyl, and alkyl/aryl ketones, including heteroatoms. Methyl alkyl ketones gave the corresponding 2-methyl-3-substituted indoles in a regioselective manner. This protocol allowed us to expand the preparation of indoles having high compatibility with not only electron-donating and electron-withdrawing groups but also N- and O-protecting functional groups.

Method for preparing gamma-eudistomin U

The invention belongs to the technical field of medicines, and discloses a simple and convenient method for preparing gamma-eudistomin U. According to the method, 4-piperidone and phenylhydrazine are used as initial raw materials, and gamma-eudistomin U is synthesized through a three-step reaction. Reagents used in the method are commonly used reagents in laboratories, and coupling reaction of key steps can be completed at room temperature. Therefore, the required materials are easy to obtain, the cost is low, the reaction operation is simple, the treatment is easy, and a large amount of gamma-eudistomin U can be obtained for medicine research and development.

Selective C-H Olefination of Indolines (C5) and Tetrahydroquinolines (C6) by Pd/S,O-Ligand Catalysis

Herein, we report a highly selective C-H olefination of directing-group-free indolines (C5) and tetrahydroquinolines (C6) by Pd/S,O-ligand catalysis. In the presence of the S,O-ligand, a wide range of challenging indolines, tetrahydroquinolines, and olefins was efficiently olefinated under mild reaction conditions. The synthetic potential of this methodology was demonstrated by the efficient olefination of several indoline-based natural products.

Biomimetic Oxidative Coupling Cyclization Enabling Rapid Construction of Isochromanoindolenines

Herein, we report a biomimetic oxidative coupling cyclization strategy for the highly efficient functionalization of tetrahydrocarbolines (THCs). This process enables rapid access to complex isochromanoindolenine scaffolds in moderate to excellent yields.

The Witkop-Winterfeldt oxidation converts tetrahydropyridoindoles into pyrroloquinolones and cinnolines by an unprecedented scaffold rearrangement

The Fischer indole reaction between phenylhydrazines and tosyl-4-piperidone furnishes tetrahydropyrido[4,3-b]indoles. In a Witkop-Winterfeldt-oxidation using ozone such indole derivatives are converted into medium-sized dicarbonyl ring systems, which cycl