Preraration and Photolysis of 1-Heterosubstitute 1-(1-Alkenyl)benzotriazoles

Johnson, A. Peter; Dutton, Jonathan K.; Pleynet, David P. M.

doi:10.3987/com-93-s164

Cited by 9 publications

(3 citation statements)

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“…First, Süs, Horner and co‐workers described the photolysis of diazoindolenine 349 in cyclooctene 350 to furnish a product that was tentatively assigned as being spirocyclic cyclopropane 351 , in an undisclosed yield. Johnson and co‐workers later reported the photolysis of benzotriazole 352 , which is presumed to form a diradical species 354 that undergoes subsequent cyclisation to form the spirocyclic indolenine 353 in low yield …”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Synthesis of Spirocyclic Indolenines

James

O’Brien

Taylor

et al. 2015

Chemistry A European J

299

119

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This Review provides an in-depth account of the synthesis of spirocyclic indolenines. Over the last 77 years, a wide array of diverse synthetic methods has been developed in order to generate these synthetically useful and biologically important spirocyclic scaffolds. The main synthetic strategies discussed are grouped into three main categories, namely interrupted Fischer indolisations, dearomatisation reactions of indoles and condensation reactions. The historical background, common synthetic challenges, current state-of-the-art and future perspectives of this field are examined.

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Section: Miscellaneous Reactionsmentioning

confidence: 99%

Synthesis of Spirocyclic Indolenines

James

O’Brien

Taylor

et al. 2015

Chemistry A European J

299

119

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“…15 The synthesis of 1-(1-alkenyl)benzotriazoles is of current interest. 16,17 We now wish to report a simple and convenient method for the synthesis of 1-(1-alkenyl)benzotriazoles by the nucleophilic substitution reaction of benzotriazole anion and vinyl(phenyl)iodonium salts.Recently our research interest is in the chemistry of hypervalent iodine compounds. Because of an excellent leaving group ability of a phenyliodonyl moiety, vinyl(phenyl)iodonium salts undergo nucleophilic vinyl substitutions under mild conditions, thus providing a useful route for the synthesis of various kinds of olefins.…”

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confidence: 99%

mentioning

confidence: 99%

Hypervalent Iodine in Synthesis 73: A New Stereoselective Synthesis of 1-(1-alkenyl) Benzotriazoles by the reaction of Alkenyl(phenyl)iodonium Salts with Benzotriazole

Zhang

Chen

2002

Journal of Chemical Research

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We report the preparation of 1-(1-alkenyl)benzotriazoles from alkenyl (phenyl)iodonium salts and benzotriazole. The reaction offers a simple and convenient route for the stereoselective synthesis of 1-(1-alkenyl)benzotriazoles. In addition, present method is particularly efficient for preparing 1-(1-alkenyl)benzotriazoles with amino-, acyl- and alkoxycarbonyl substituents, which were difficult to prepare by conventional methods.

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Mild Copper‐Catalyzed Vinylation Reactions of Azoles and Phenols with Vinyl Bromides

Taillefer¹,

Ouali²,

Renard³

et al. 2006

Chemistry A European J

122

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An efficient and straightforward copper-catalyzed method allowing vinylation of N- or O-nucleophiles with di- or trisubstituted vinyl bromides is reported. The procedure is applicable to a broad range of substrates since N-vinylation of mono-, di-, and triazoles as well as O-vinylation of phenol derivatives can be performed with catalytic amounts of copper iodide and inexpensive nitrogen ligands 3 or 8. In the case of more hindered vinyl bromides, the use of the original bidentate chelator 8 was shown to be more efficient to promote the coupling reactions than our key tetradentate ligand 3. The corresponding N-(1-alkenyl)azoles and alkenyl aryl ethers are obtained in high yields and selectivities under very mild temperature conditions (35-110 degrees C for N-vinylation reactions and 50-80 degrees C for O-vinylation reactions). Moreover, to our knowledge, this method is the first example of a copper-catalyzed vinylation of various azoles. Finally, this protocol, practical on a laboratory scale and easily adaptable to an industrial scale, is very competitive compared to the existing methods that allow the synthesis of such compounds.

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Preraration and Photolysis of 1-Heterosubstitute 1-(1-Alkenyl)benzotriazoles

Cited by 9 publications

References 0 publications

Synthesis of Spirocyclic Indolenines

Synthesis of Spirocyclic Indolenines

Hypervalent Iodine in Synthesis 73: A New Stereoselective Synthesis of 1-(1-alkenyl) Benzotriazoles by the reaction of Alkenyl(phenyl)iodonium Salts with Benzotriazole

Mild Copper‐Catalyzed Vinylation Reactions of Azoles and Phenols with Vinyl Bromides

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