Acetylenic sulfones and sulfoxides

Laba, V. I.; Polievktov, M. K.; Prilezhaeva, E. N.; Mairanovskii, S. G.

doi:10.1007/bf00906610

Cited by 5 publications

(4 citation statements)

References 11 publications

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“…Parent N , N -dipropyl- and N , N -dimethylpropiolamides were prepared according to the published procedure . Ethynyl sulfones and ethynyl isopropyl ketone were prepared by known methods. Schiff bases were prepared by the condensation of 2-aminothiazoles with aldehydes …”

Section: Methodsmentioning

confidence: 99%

Synthesis of Imidazo[2,1-b]thiazoles via Copper-Catalyzed A³-Coupling in Batch and Continuous Flow

et al. 2017

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A straightforward method for the synthesis of functionalized imidazo[2,1-b]thiazoles starting from benzaldehydes, 2-aminothiazoles, and alkynes under copper(I,II) catalysis was developed. The protocol allows the construction of a variety of aryl-substituted imidazo[2,1-b]benzothiazoles, -[2,1-b]thiazoles, and -[2,1-b][1,3,4]thiadiazoles. The reactions were easy to perform affording most of the desired products in 33-93% yields. The intensification of the process in a continuous-flow reactor increases the products' yields up to quantitative.

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Section: Methodsmentioning

confidence: 99%

Synthesis of Imidazo[2,1-b]thiazoles via Copper-Catalyzed A³-Coupling in Batch and Continuous Flow

et al. 2017

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“…To examine the strategy outlined in Scheme , -azabicycle 67 was prepared by [4 + 2] cycloaddition of N -Boc pyrrole and 2-(ethynylsulfonyl)propane 66 (63%, Scheme ). 2-(Ethynylsulfonyl)propane 66 has previously been prepared in five steps from acetylene, but it was more conveniently made by following a one-pot protocol for forming S -alkyl ynethiol ethers from trichloroethylene, followed by oxidation with peracetic acid …”

Section: Resultsmentioning

confidence: 99%

Stereocontrolled Syntheses of Kainoid Amino Acids from 7-Azabicyclo[2.2.1]heptadienes Using Tandem Radical Addition-Homoallylic Radical Rearrangement

2005

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[reaction; see text] N-Boc syn-7-(2-hydroxyethyl)-4-(alkyl or aryl)sulfonyl-2-azabicyclo[2.2.1]hept-5-enes serve as precursors in syntheses of the neuroexcitants 3-(carboxymethyl)pyrrolidine-2,4-dicarboxylic acid 43, alpha-kainic acid 12, alpha-isokainic acid 14, and alpha-dihydroallokainic acid 77. The key step in these syntheses is the intermolecular radical addition of 2-iodoethanol to a N-Boc 2-(alkyl or aryl)sulfonyl-7-azabicyclo[2.2.1]heptadiene 7 to induce nitrogen-directed homoallylic radical rearrangement. Oxidative cleavage of the resulting 2-azabicyclo[2.2.1]hept-5-enes provide straightforward access to polysubstituted pyrrolidines and, in particular, an efficient entry to the kainoid amino acids.

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“…Currently, these two oxidizing reagents remain the most used for this purpose (Scheme ) . Peroxybenzoic acid and peroxyethanoic acid have also been used for this purpose, although to a lesser extent.…”

Section: Oxidation Of Alkynyl Sulfides With Peroxidesmentioning

confidence: 99%

“…Thus, there are few reports specifically targeted to their synthesis. The first such report was a polarographic study of six different alkynyl sulfones that were synthesized by Mairanovskii and coworkers in 1969 . This study highlights the use of peroxyethanoic acid (AcO 3 H) as an oxidizing agent (Scheme ).…”

Section: Oxidation Of Alkynyl Sulfides With Peroxidesmentioning

confidence: 99%

Synthesis of Alkynyl Sulfones

et al. 2019

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Alkynyl sulfones are organic structures of high synthetic interest, since they can react with nucleophiles by conjugated addition (Michael addition) or through anti-Michael addition. Such interesting reactive properties make these compounds important intermediates in the synthesis of more complex organic molecules or naturally occurring products. Despite the use of alkynyl sulfones as starting materials (or intermediates), there was not a real interest in developing specific method-ologies for their synthesis. Therefore, the synthesis of alkynyl sulfones remained unchanged for a long time. It was not until the 1970s that studies focused on the development of new synthetic routes began to emerge. This Mini Review presents the advances and the state of the art of the synthesis of alkynyl sulfones. Methodologies described in the manuscript are classified according to the starting materials and reagents used. Moreover, every class is arranged in chronological order.

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Acetylenic sulfones and sulfoxides

Cited by 5 publications

References 11 publications

Synthesis of Imidazo[2,1-b]thiazoles via Copper-Catalyzed A³-Coupling in Batch and Continuous Flow

Synthesis of Imidazo[2,1-b]thiazoles via Copper-Catalyzed A³-Coupling in Batch and Continuous Flow

Stereocontrolled Syntheses of Kainoid Amino Acids from 7-Azabicyclo[2.2.1]heptadienes Using Tandem Radical Addition-Homoallylic Radical Rearrangement

Synthesis of Alkynyl Sulfones

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Acetylenic sulfones and sulfoxides

Cited by 5 publications

References 11 publications

Synthesis of Imidazo[2,1-b]thiazoles via Copper-Catalyzed A3-Coupling in Batch and Continuous Flow

Synthesis of Imidazo[2,1-b]thiazoles via Copper-Catalyzed A3-Coupling in Batch and Continuous Flow

Stereocontrolled Syntheses of Kainoid Amino Acids from 7-Azabicyclo[2.2.1]heptadienes Using Tandem Radical Addition-Homoallylic Radical Rearrangement

Synthesis of Alkynyl Sulfones

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Synthesis of Imidazo[2,1-b]thiazoles via Copper-Catalyzed A³-Coupling in Batch and Continuous Flow

Synthesis of Imidazo[2,1-b]thiazoles via Copper-Catalyzed A³-Coupling in Batch and Continuous Flow