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An efficient metal-free and catalyst-free C–S/C–O bond-formation strategy: synthesis of pyrazole-conjugated thioamides and amides

Shubham Sharma, Dharmender Singh, Sunit Kumar, Vaishali Vaishali, Rahul Jamra, Naveen Banyal, Deepika, Chandi C. Malakar, Virender Singh

2023Beilstein Journal of Organic Chemistry21 citationsDOIOpen Access PDF

Abstract

An operationally simple and metal-free approach is described for the synthesis of pyrazole-tethered thioamide and amide conjugates. The thioamides were generated by employing a three-component reaction of diverse pyrazole C-3/4/5 carbaldehydes, secondary amines, and elemental sulfur in a single synthetic operation. The advantages of this developed protocol refer to the broad substrate scope, metal-free and easy to perform reaction conditions. Moreover, the pyrazole C-3/5-linked amide conjugates were also synthesized via an oxidative amination of pyrazole carbaldehydes and 2-aminopyridines using hydrogen peroxide as an oxidant.

Topics & Concepts

PyrazoleChemistryThioamideCombinatorial chemistryCatalysisAmideConjugated systemAminationOrganic chemistryHydrogen peroxideReductive aminationPolymerSynthesis of heterocyclic compoundsSynthesis and Reactivity of Sulfur-Containing CompoundsSynthesis and Catalytic Reactions
An efficient metal-free and catalyst-free C–S/C–O bond-formation strategy: synthesis of pyrazole-conjugated thioamides and amides | Litcius