23077-27-2

Upstream product

• 42738-99-8 11-hydroxytetrahydrocarbazolenine 
• 6004-60-0 1-cyclopentylethanone 
• 100-63-0 phenylhydrazine 
• 109-99-9 tetrahydrofuran 
• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 4669-18-5 spiro[cyclopentane-1,2'-indolin]-3'-one 
• 62367-63-9 N-[1-Cyclopentyl-eth-(E)-ylidene]-N'-phenyl-hydrazine 
• 33240-34-5 cyclopentylmagnesium bromide 
• 138850-29-0 6'-methyl-2',3',4',5'-tetrahydro-[1,1'-biphenyl]-2-amine 
• 32363-21-6 2-methyl-1-cyclohexenyl triflate 
• 191171-55-8 2-anilineboronic acid pinacol ester 
• 615-36-1 2-bromoaniline 
• 95-20-5 2-methyl-1H-indole 

Downstream Products

• 85095-32-5 1',2'-dimethyl-spiro[cyclopentane-1,3'-indolium]; iodide 
• 41058-67-7 spiro[cyclopentane-1,3'-indol]-2'(1'H)-one 

Relevant academic research and scientific papers

Dearomatizing Spiroannulation Reagents: Direct Access to Spirocycles from Indoles and Dihalides

Unfunctionalized indoles can be directly converted into 3,3′-spirocyclic indolenines and indolines upon reaction with electrophilic dihalides in the presence of t-BuOK/BEt3. This double C-C bond forming reaction, which simultaneously generates a quaternary spirocyclic center, typically proceeds in high yield and has good functional group tolerance. In contrast to existing dearomatizing spirocyclization approaches, there is no need to prepare a prefunctionalized aromatic precursor, enabling faster access to valuable spirocyclic products from simple, commercially available aromatics in one step.

I(III)-catalyzed oxidative cyclization - Migration tandem reactions of unactivated anilines

An I(III)-catalyzed oxidative cyclization-migration tandem reaction using Selectfluor as the oxidant was developed that converts unactivated anilines into 3H-indoles is reported herein. The reaction requires as little as 1 mol % of the iodocatalyst and is mild, tolerating pyridine and thiophene functional groups, and the dependence of the diastereoselectivity of the process on the identity of the iodoarene or iodoalkane precatalyst suggests that the catalyst is present for the stereochemical determining C-N bond forming step.

Oxidation of Nonactivated Anilines to Generate N-Aryl Nitrenoids

A low-temperature, protecting-group-free oxidation of 2-substituted anilines has been developed to generate an electrophilic N-aryl nitrenoid intermediate that can engage in C-NAr bond formation to construct functionalized N-heterocycles. The exposure of 2-substituted anilines to PIFA and trifluoroacetic acid or 10 mol percent Sc(OTf)3 triggers nitrenoid formation, followed by productive and selective C-NAr and C-C bond formation to yield spirocyclic- or bicyclic 3H-indoles or benzazepinones. Our experiments demonstrate the breadth of these oxidative processes, uncover underlying fundamental elements that control selectivity, and demonstrate how the distinct reactivity patterns embedded in N-aryl nitrenoid reactive intermediates can enable access to functionalized 3H-indoles or benzazepinones.

Promoting reductive tandem reactions of nitrostyrenes with Mo(CO)6 and a palladium catalyst to produce 3 h -indoles

The combination of Mo(CO)6 and 10 mol % of palladium acetate catalyzes the transformation of 2-nitroarenes to 3H-indoles through a tandem cyclization-[1,2] shift reaction of in situ generated nitrosoarenes. Mo(CO)6 appears to have dual roles in this transformation: generate CO and promote C-N bond formation to increase the yield of the N-heterocycle product.

Reactions of some Heterocyclic Quaternary Salts with Trifluoroacetic Anhydride

Treatment of the methiodides of 4a-methyl-1,2,3,4-tetrahydro-4aH-carbazole, 2-methyl-3H-indole-3-spirocyclopentane, 2-methylbenzothiazole, and 2-methylquinoline with trifluoroacetic anhydride afforded trifluoromethyl ketones.Some reactions of these enamin