Direct access to 2-aryl-3-cyanothiophenes by a base-catalyzed one-pot two-step three-component reaction of chalcones with benzoylacetonitriles and elemental sulfur

Lai, Nang Duy; Nguyen, Thu Trang; Nguyen, Nhu Ngan Ha; Retailleau, Pascal; Mac, Hung Dinh; Nguyễn, Thanh Bình

doi:10.1039/d2qo00526c

Cited by 14 publications

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References 49 publications

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“…During the course of our study on the use of sulfur as a versatile sulfurating and oxidizing agent for the synthesis of thiophenes from Michael adducts MA prepared in situ from acetonitriles 1 and chalcones 2 , a wide range of substituents R were investigated (Scheme ). With arylacetonitriles 1a (R = Ar) or cyanoacetates (R = CO 2 Alk) as well as N-substituted cyanoacetamides (R = CONHAlk/Ar) 1b , 2-aminothiophenes 3aa and 3ab were formed.…”

Section: Introductionmentioning

confidence: 99%

Sulfur-Promoted Oxidative Condensation of Chalcones with Unsubstituted Cyanoacetamide in DMSO: Access to 3-Cyanopyrid-2-ones

et al. 2023

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Section: Introductionmentioning

confidence: 99%

Sulfur-Promoted Oxidative Condensation of Chalcones with Unsubstituted Cyanoacetamide in DMSO: Access to 3-Cyanopyrid-2-ones

et al. 2023

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“…6 S atom has a higher polarization than other heteroatoms (N, O, etc . ), which can be used as a reductant, 7 oxidant, 8 catalyst (activator), 9 or a building block in a reaction. 10…”

Section: Introductionmentioning

confidence: 99%

Fe/S cluster catalyzed cascade cyclization of N,S-1,6-enynes for the synthesis of thieno[3,4-b]indoles

2023

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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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Direct access to 2-aryl-3-cyanothiophenes by a base-catalyzed one-pot two-step three-component reaction of chalcones with benzoylacetonitriles and elemental sulfur

Abstract: 3-Cyanothiophene is an important heterocyclic scaffold in bioorganic and medicinal chemistry as a useful synthetic intermediate as well as in material sciences as a privilege motif for photovoltaic development. Herein,...

Cited by 14 publications

References 49 publications

Sulfur-Promoted Oxidative Condensation of Chalcones with Unsubstituted Cyanoacetamide in DMSO: Access to 3-Cyanopyrid-2-ones

Sulfur-Promoted Oxidative Condensation of Chalcones with Unsubstituted Cyanoacetamide in DMSO: Access to 3-Cyanopyrid-2-ones

Fe/S cluster catalyzed cascade cyclization of N,S-1,6-enynes for the synthesis of thieno[3,4-b]indoles

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

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