InCl3 catalyzed synthesis of thiophene derivatives via vinyl azides and β-ketothioamides

Zhang, Li-Ming; Wen, Li‐Rong; Niu, Xiao-Dong; Guo, Wei‐Si; Li, Ming

doi:10.1016/j.tet.2023.133412

Cited by 3 publications

(1 citation statement)

References 61 publications

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“…On the one hand, the carbonyl group in KTAs renders them susceptible to nucleophilic attack, allowing them to act as substrates for nucleophilic addition and leading to the formation of many heterocyclic compounds [1]. On the other hand, the thioamide functional group in KTAs undergoes isomerization to generate thiol [2], allowing KTAs to participate in synthesis. Multiple heterocycles, such as thiazoles [3,4], piperidines [5], pyran [6] and fused heterocycles [7,8], have been efficiently constructed.…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of Pyrrole Disulfides Catalyzed by Lipase in Ethanol

Wen,

Xu,

et al. 2023

Catalysts

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Disulfides, as fundamental scaffolds, are widely present in peptides, natural products, and pharmaceutical molecules. However, traditional synthesis of disulfides often involves the utilization of toxic reagents or environmentally unfriendly reaction conditions. In this work, a green and efficient method was developed for synthesizing pyrrole disulfides using β-ketothioamides and ethyl cyanoacetate as substrates, with lipase serving as a catalyst. Under the optimal conditions (β-Ketothioamides (1 mmol), ethyl cyanoacetate (1 mmol), PPL (200 U), and EtOH (5 mL)), lipase leads to the formation of pyrrole disulfides in yields of up to 88% at 40 °C. The related mechanism is also speculated in this paper. This approach not only presents a new application of lipase in enzyme catalytic promiscuity, but also offers a significant advancement in the synthetic pathway for pyrrole disulfides and aligns with the current mainstream research direction of green chemistry, contributing to the further development of environmentally friendly biocatalytic processes.

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Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of Pyrrole Disulfides Catalyzed by Lipase in Ethanol

Wen,

Xu,

et al. 2023

Catalysts

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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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One‐Pot Synthesis of 2‐Aminothiophenes by Au(I)‐Catalyzed Cascade Reaction Including Hydrothiolation, Thio‐Claisen Rearrangement, and Cycloisomerization

Oonishi,

Ueda,

Sato

2024

Adv Synth Catal

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The cascade reaction of ynamides with propargyl thiols by Au(I) catalysis involving regioselective hydrothiolation, thio‐Claisen rearrangement, and cycloisomerization to generate 2‐aminothiophenes in a one‐pot manner is described. In this reaction, the selection of reaction temperature is crucial, with the initial step, namely hydrothiolation, conducted at a low temperature (40°C), followed by the subsequent reaction requiring an increase in temperature (>110°C). Furthermore, it was revealed that multi‐substituted anilines could be synthesized efficiently from the resulting 2‐aminothiophenes.

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InCl3 catalyzed synthesis of thiophene derivatives via vinyl azides and β-ketothioamides

Cited by 3 publications

References 61 publications

Efficient Synthesis of Pyrrole Disulfides Catalyzed by Lipase in Ethanol

Efficient Synthesis of Pyrrole Disulfides Catalyzed by Lipase in Ethanol

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

One‐Pot Synthesis of 2‐Aminothiophenes by Au(I)‐Catalyzed Cascade Reaction Including Hydrothiolation, Thio‐Claisen Rearrangement, and Cycloisomerization

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