One-step preparation of novel 1-(<i>N</i>-indolyl)-1,3-butadienes by base-catalysed isomerization of alkynes as an access to 5-(<i>N</i>-indolyl)-naphthoquinones

Diez, C.; Fernández, Julián Francisco; Venosa, Gabriela Mariana Di; Casas, Adriana; Diez, Reinaldo Pis; Palermo, Jorge Alejandro

doi:10.1039/c8ra05208e

RSC Adv.

2018

DOI: 10.1039/c8ra05208e

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One-step preparation of novel 1-(N-indolyl)-1,3-butadienes by base-catalysed isomerization of alkynes as an access to 5-(N-indolyl)-naphthoquinones

C. Diez

Julián Francisco Fernández

Gabriela Mariana Di Venosa

et al.

Abstract: A series of novel 1-(N-indolyl)-1,3-butadienes, was easily prepared in one step and used for the synthesis of 5-(N-indolyl) naphthoquinones.

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Cited by 3 publications

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Sc(OTf)₃‐Catalyzed Synthesis of 3‐Substituted Lawsones through a Buchner‐Curtius‐Schlotterbeck Reaction

Gogula,

Prasanna,

Sridhar

et al. 2024

Eur J Org Chem

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An efficient strategy has been developed for the synthesis of 3‐substituted lawsones using a catalytic amount of Sc(OTf)3 in toluene at ‐78 °C through a Buchner‐Curtius‐Schlotterbeck reaction. It is a versatile method to produce a large number of 3‐aryl, 3‐styryl, 3‐alkyl, and 3‐heteroaryl substituted lawsones under mild conditions. This is a first report on the synthesis of 3‐substituted lawsones in high to excellent yields in short reaction times.

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Sc(OTf)₃‐Catalyzed Synthesis of 3‐Substituted Lawsones through a Buchner‐Curtius‐Schlotterbeck Reaction

Gogula,

Prasanna,

Sridhar

et al. 2024

Eur J Org Chem

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Remote Functionalization by Pd-Catalyzed Isomerization of Alkynyl Alcohols

Scaringi,

Leforestier,

Mazet

2024

J. Am. Chem. Soc.

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In recent years, progress has been made in the development of catalytic methods that allow remote functionalizations based on alkene isomerization. In contrast, protocols based on alkyne isomerization are comparatively rare. Herein, we report a general Pd-catalyzed long-range isomerization of alkynyl alcohols. Starting from aryl-, heteroaryl-, or alkyl-substituted precursors, the optimized system provides access preferentially to the thermodynamically more stable α,β-unsaturated aldehydes and is compatible with potentially sensitive functional groups. We showed that the migration of both π-components of the carbon−carbon triple bond can be sustained over several methylene units. Computational investigations served to shed light on the key elementary steps responsible for the reactivity and selectivity. These include an unorthodox phosphine-assisted deprotonation rather than a more conventional β-hydride elimination in the final tautomerization event.

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A.E.Favorskii’s scientific legacy in modern organic chemistry: prototropic acetylene – allene isomerization and the acetylene zipper reaction

Danilkina¹,

Vasil'eva²,

Балова³

2020

Russ. Chem. Rev.

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Alexei Evgrafovich Favorskii was an outstanding organic chemist who left a great scientific legacy as a result of long time and fruitful work. Most of the theoretically and practically important discoveries of A.E.Favorskii were made in the chemistry of acetylene and its derivatives. Nowadays, the reactions discovered by him, which include acetylene – allene isomerization, the Favorskii and retro-Favorskii reactions, the Favorskii rearrangement and the vinylation reaction, are widely used in industry and in laboratory synthesis. This review summarizes the main scientific achievements of A.E.Favorskii, as well as their development in modern organic chemistry. Much consideration is given to acetylene – allene isomerization as a convenient method for the synthesis of methyl-substituted acetylenes and to the acetylene zipper reaction as a synthetic tool for obtaining terminal acetylenes. The review presents examples of the application of these reactions in modern organic synthesis of complex molecules, including natural compounds and their analogues. The bibliography includes 266 references.

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One-step preparation of novel 1-(N-indolyl)-1,3-butadienes by base-catalysed isomerization of alkynes as an access to 5-(N-indolyl)-naphthoquinones

Abstract: A series of novel 1-(N-indolyl)-1,3-butadienes, was easily prepared in one step and used for the synthesis of 5-(N-indolyl) naphthoquinones.

Cited by 3 publications

References 34 publications

Sc(OTf)₃‐Catalyzed Synthesis of 3‐Substituted Lawsones through a Buchner‐Curtius‐Schlotterbeck Reaction

Sc(OTf)₃‐Catalyzed Synthesis of 3‐Substituted Lawsones through a Buchner‐Curtius‐Schlotterbeck Reaction

Remote Functionalization by Pd-Catalyzed Isomerization of Alkynyl Alcohols

A.E.Favorskii’s scientific legacy in modern organic chemistry: prototropic acetylene – allene isomerization and the acetylene zipper reaction

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One-step preparation of novel 1-(N-indolyl)-1,3-butadienes by base-catalysed isomerization of alkynes as an access to 5-(N-indolyl)-naphthoquinones

Abstract: A series of novel 1-(N-indolyl)-1,3-butadienes, was easily prepared in one step and used for the synthesis of 5-(N-indolyl) naphthoquinones.

Cited by 3 publications

References 34 publications

Sc(OTf)3‐Catalyzed Synthesis of 3‐Substituted Lawsones through a Buchner‐Curtius‐Schlotterbeck Reaction

Sc(OTf)3‐Catalyzed Synthesis of 3‐Substituted Lawsones through a Buchner‐Curtius‐Schlotterbeck Reaction

Remote Functionalization by Pd-Catalyzed Isomerization of Alkynyl Alcohols

A.E.Favorskii’s scientific legacy in modern organic chemistry: prototropic acetylene – allene isomerization and the acetylene zipper reaction

Contact Info

Product

Resources

About

Sc(OTf)₃‐Catalyzed Synthesis of 3‐Substituted Lawsones through a Buchner‐Curtius‐Schlotterbeck Reaction

Sc(OTf)₃‐Catalyzed Synthesis of 3‐Substituted Lawsones through a Buchner‐Curtius‐Schlotterbeck Reaction