138850-29-0

Upstream product

• 138850-21-2 4-methyl-N-(2-(2-methylcyclohex-1-enyl)-phenyl)benzenesulfinamide 
• 1007834-63-0 N-(cyclohex-1-enylmethyl)benzenamine 
• 1121-18-2 2-methyl-2-cyclohexen-1-one 
• 32363-21-6 2-methyl-1-cyclohexenyl triflate 
• 191171-55-8 2-anilineboronic acid pinacol ester 
• 615-36-1 2-bromoaniline 
• 138866-20-3 (+/-)-(5S^*,4aS^*,10bS^*)-1,2,3,4,4a,10b-hexahydro-4a-methyl-5-(4-methylphenyl)-5λ⁴-dibenzo-1,2-thiazine-5-oxide 
• 134970-88-0 (+/-)-(5S*,4aS*,10bS*)-1,2,3,4,4a,10b-hexahydro-5-(4-methylphenyl)-5λ⁴-dibenzo<1,2>thiazine 5-oxide 

Downstream Products

• 23077-27-2 2'-methylspiro[cyclopentane-1,3'-indole] 

Relevant academic research and scientific papers

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.

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.

Synthesis of cycloalkanoindoles, the carba analogs of physostigmine

The title compounds 9 were prepared by combined aza-Claisen rearrangement/intramolecular ring-closure reaction of N-allylaniline derivatives 3, followed by BBr3 mediated cleavage of methoxy group and subsequent formation of the phenylcarbamyl d

The conversion of benzothiazines to 2-alkenyl anilines

Upon treatment with excess potassium dimsylate in DMSO benzothiazines 1a-1j undergo an elimination of the sulfoximine functional group to give 2-alkenylsulfinanilides nonstereoselectively in good to excellent yield. These are easily converted to the corre