Construction of Novel Tetrahydro‐<i>β</i>‐carboline‐1‐thione Spirooxindoles by Brønsted Acid Mediated Formal [3+3] Cyclization of 3‐Indolylmethanols with 3‐Isothiocyanato Oxindoles

A catalyst-free self-catalyzed [3+2] cycloaddition reaction of isatin-derived α-(trifluoromethyl)imines with vinylpyridines is reported. The reaction offers a straightforward and atom-economical procedure for the preparation of a series of 5'-trifluoromethyl-spiro[pyrrolidin-3,2'-oxindoles] in excellent yields and diastereoselectivities. The reaction mechanism has been investigated by control experiments, DFT calculation of pK values and the kinetic profiles, revealing that this reaction featured the mutual activation between isatin-derived α-(trifluoromethyl)imines and vinylpyridine to generate the reactive species.

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Highly Efficient and Diastereoselective Construction of Trifluoromethyl‐Containing Spiro[pyrrolidin‐3,2′‐oxindole] by a Catalyst‐free Mutually Activated [3+2] Cycloaddition Reaction

Gui

Gao

Wei

et al. 2018

Chemistry A European J

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Rapid One‐Pot Access to Unique 3,4‐Dihydrothiopyrano[3,4‐b]indol‐1(9H)‐imines via Bi(OTf)₃‐Catalysed Tandem Friedel–Crafts Alkylation/Thia‐Michael Addition

2018

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A highly efficient and atom economical one‐pot annulation strategy for novel tetrahydrothiopyrano[3,4‐b]indoles is presented. This protocol involves a Bi(OTf)3 catalyzed tandem Friedel–Crafts alkylation and intramolecular thia‐Michael addition reactions to furnish target molecules in an efficient manner. The method works effectively on substrates with unprotected indoles and also it is successfully employed to make tetrahydrothiepino[3,4‐b]indoles. The scaffolds synthesized are diverse and first of the kind. The reaction is practically simple with broad substrate scope and vast functional group compatibility.

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A Catalyst‐Free Self‐Catalyzed [3+2] Cycloaddition Reaction of 3‐Isothiocyanato Oxindoles and Vinylpyridines

2018

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A catalyst‐free self‐catalyzed [3+2] cycloaddition reaction of 3‐isothiocyanato oxindoles with vinylpyridines has been established, affording the desired products in high yields (up to 97 %) with moderate to good diastereoselectivities (up to 11:1) under mild conditions. The reaction mechanism has been investigated by control experiments, DFT calculations of pKa values and the kinetic studies, revealing that this reaction featured the mutual activation between 3‐isothiocyanato oxindole and vinylpyridine to generate the reactive species. Furthermore, these products could be easily transformed into the corresponding methylated and hydroxylated products under basic conditions.

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Construction of Novel Tetrahydro‐β‐carboline‐1‐thione Spirooxindoles by Brønsted Acid Mediated Formal [3+3] Cyclization of 3‐Indolylmethanols with 3‐Isothiocyanato Oxindoles

Cited by 6 publications

References 67 publications

Highly Efficient and Diastereoselective Construction of Trifluoromethyl‐Containing Spiro[pyrrolidin‐3,2′‐oxindole] by a Catalyst‐free Mutually Activated [3+2] Cycloaddition Reaction

Highly Efficient and Diastereoselective Construction of Trifluoromethyl‐Containing Spiro[pyrrolidin‐3,2′‐oxindole] by a Catalyst‐free Mutually Activated [3+2] Cycloaddition Reaction

Rapid One‐Pot Access to Unique 3,4‐Dihydrothiopyrano[3,4‐b]indol‐1(9H)‐imines via Bi(OTf)₃‐Catalysed Tandem Friedel–Crafts Alkylation/Thia‐Michael Addition

A Catalyst‐Free Self‐Catalyzed [3+2] Cycloaddition Reaction of 3‐Isothiocyanato Oxindoles and Vinylpyridines

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Construction of Novel Tetrahydro‐β‐carboline‐1‐thione Spirooxindoles by Brønsted Acid Mediated Formal [3+3] Cyclization of 3‐Indolylmethanols with 3‐Isothiocyanato Oxindoles

Cited by 6 publications

References 67 publications

Highly Efficient and Diastereoselective Construction of Trifluoromethyl‐Containing Spiro[pyrrolidin‐3,2′‐oxindole] by a Catalyst‐free Mutually Activated [3+2] Cycloaddition Reaction

Highly Efficient and Diastereoselective Construction of Trifluoromethyl‐Containing Spiro[pyrrolidin‐3,2′‐oxindole] by a Catalyst‐free Mutually Activated [3+2] Cycloaddition Reaction

Rapid One‐Pot Access to Unique 3,4‐Dihydrothiopyrano[3,4‐b]indol‐1(9H)‐imines via Bi(OTf)3‐Catalysed Tandem Friedel–Crafts Alkylation/Thia‐Michael Addition

A Catalyst‐Free Self‐Catalyzed [3+2] Cycloaddition Reaction of 3‐Isothiocyanato Oxindoles and Vinylpyridines

Contact Info

Product

Resources

About

Rapid One‐Pot Access to Unique 3,4‐Dihydrothiopyrano[3,4‐b]indol‐1(9H)‐imines via Bi(OTf)₃‐Catalysed Tandem Friedel–Crafts Alkylation/Thia‐Michael Addition