Cu(II)-catalyzed one-pot synthesis of fully substituted dihydrothiophenes and thiophenes from thioamides and enynones

Wen, Min; Sun, Peipei; Luo, Xiaoyan; Deng, Wei‐Ping

doi:10.1016/j.tet.2018.02.035

Cited by 26 publications

(5 citation statements)

References 40 publications

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“…Thioamides are important intermediates in organic synthesis, playing a significant role in synthesizing heterocyclic compounds such as pyrrole [1] , pyrazole [2] , imidazole [3] , thiazole [4] and thiophene [5] . A method for the selective synthesis of o-halobenzothioamide derivatives from the thiolysis of o-halobenzonitrile mediated by CO 2 has been previously developed by our group [6] .…”

Section: Background and Originality Contentmentioning

confidence: 99%

Synthesis of Benzothioamide Derivatives from Benzonitriles and Sulfur-containing Ionic Liquids in Supercritical CO2

Sang,

Wang,

Feng

et al. 2024

Preprint

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A simple, efficient and green method has been developed for the synthesis of benzothioamide from benzonitrile in supercritical CO2, which could be used to synthesize various benzothioamide derivatives efficiently without organic solvent. Notably, some sulfur-containing ionic liquids were prepared and they could promote the thiolysis of benzonitrile to produce benzothioamide in an excellent yield. Moreover, the investigation on the reaction mechanism showed that the acid-base property of the reaction solution was key to the thiolysis of benzonitrile mediated by the sulfur-containing ionic liquids.

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Section: Background and Originality Contentmentioning

confidence: 99%

Synthesis of Benzothioamide Derivatives from Benzonitriles and Sulfur-containing Ionic Liquids in Supercritical CO2

Sang,

Wang,

Feng

et al. 2024

Preprint

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“…Thioamide is a well‐known functional group due to its presence in many structures. This group serves as a synthon for the synthesis of polymers [ 1,2 ] and also a variety of heterocycles such as thiazols, [ 3 ] thiazolines, [ 4 ] thiophens, [ 5 ] benzothiazols, [ 6 ] triazines [ 7 ] and tetrazoles. [ 8 ] Thioamides are applied in the asymmetric synthesis, [ 9 ] and are also used for the modification of peptides.…”

Section: Introductionmentioning

confidence: 99%

Copper‐catalyzed synthesis of α‐ketothioamides from ketones

Abdollahi

Ghaderi

2023

J Chinese Chemical Soc

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In this paper, the conversion of acetophenone to α‐ketothioamide was reported in the presence of CuI as the catalyst and S8/DMF as the coupling partners. The presence of both KF and NaOH was found to be necessary to achieve the high yield of the product. Propiophenone and butyrophenone also reacted in the presence of phenylboronic acid as an additive. Willgerodt‐Kindler products were not observed in these reactions.

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“…Deng and co‐workers [15a] developed a metal‐free method to access 2‐aminothiophenes by treating 2‐ynals with thioamides (Scheme 1a). Cu(II)‐catalyzed synthesis of dihydrothiophenes and thiophenes from thioamides and enynones has been reported [15b] (Scheme 1b). 2‐Aminothiophenes unobtainable via the Gewald reaction were synthesized by three‐component reaction of α ‐cyanoacetates with chalcones and elemental sulfur (Scheme 1c) [15c] .…”

Section: Introductionmentioning

confidence: 99%

One‐Pot Access to Tetrasubstituted 2‐Aminothiophenes via Regio‐ and Chemoselective Domino Reactions of Dithioesters with Fumaronitrile at Room Temperature

et al. 2023

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Herein, we report a one‐pot viable protocol to synthesize tetrasubstituted 2‐aminothiophenes engaging readily accessible α‐enolic dithioesters and abundant fumaronitrile under transition metal‐free conditions at room temperature in open air. The reaction proceeds via successive Michael‐type addition/intramolecular cyclization/isomerization cascades. The added features are benign conditions, exclusive regio‐ and chemoselectivity, excellent atom‐/step‐economy, easy purification, and tolerance of wide range of functional groups of a diverse electronic and steric nature. This protocol not only provided a robust and modular approach to various 2‐aminothiophenes in moderate to excellent yields, but also demonstrated the potential of dithioesters and fumaronitrile in the challenging intermolecular cross‐coupling reactions widening the arsenal of synthetic methods.

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Cu(II)-catalyzed one-pot synthesis of fully substituted dihydrothiophenes and thiophenes from thioamides and enynones

Cited by 26 publications

References 40 publications

Synthesis of Benzothioamide Derivatives from Benzonitriles and Sulfur-containing Ionic Liquids in Supercritical CO2

Synthesis of Benzothioamide Derivatives from Benzonitriles and Sulfur-containing Ionic Liquids in Supercritical CO2

Copper‐catalyzed synthesis of α‐ketothioamides from ketones

One‐Pot Access to Tetrasubstituted 2‐Aminothiophenes via Regio‐ and Chemoselective Domino Reactions of Dithioesters with Fumaronitrile at Room Temperature

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