Abstract
AIM and Objective: The present work outlines the synthesis of pyrazoles and pyrazolo[1,5- a]pyrimidines from the reaction of 2-aryl-3-oxopropanenitrile with hydrazine monohydrate under different conditions. Reactions of 2-aryl-3-oxopropanenitrile with 2,4-pentanedione or ethyl acetoacetate furnished a mixture of highly functionalized pyridones and enamines through two different mechanistic pathways under various applied conditions.
Material and Method: 2-Aryl-3-oxopropanenitriles were prepared according to literature procedures. Other reagents and solvents were purchased and used without further purification. Reactions were carried out either at 0oC, room temperature or under reflux and product was isolated by filtration or concentration of reaction mixture.
Results: This article outlines the synthesis of 5-aminopyrazoles and/or pyrazolo[1,5-α]pyrimidines from the reaction of multi-functional 2-aryl-3-oxopropanenitrile with hydrazine monohydrate under various controlled reaction conditions. When 2-aryl-3-oxopropanenitrile reacted with 2,4-pentanedione or ethyl acetoacetate, highly functionalized enamines and pyridines were formed via two different mechanistic pathways. While, novel ethyl 6-amino-5-(4-chlorophenyl)-2-methylnicotinate was obtained from the reaction of (Z)-Ethyl-3-((Z)- 2-(4-chlorophenyl)-2-cyanovinylamino)but-2-enoate with hydrazine monohydrate in ethanol.
Conclusion: 2-Aryl-3-oxopropanenitrile proves to be a promising molecule that can be explored further to synthesize new nitrogen compounds which can be used as building blocks in synthetic heterocyclic chemistry.
Keywords: 2-Aryl-3-oxopropanenitrile, pyrazole, pyrazolopyrimidine, pyrimidone, pyridine, cyanoacetaldehyde.
Graphical Abstract
Call for Papers in Thematic Issues
Exploring the Role of Chemical Graph Theory in Advancing Current Organic Synthesis
Organic synthesis is a fundamental discipline in chemistry, crucial for the creation of complex molecules with diverse applications in pharmaceuticals, materials science, and beyond. However, the process of designing efficient synthetic routes for target molecules remains challenging. Chemical graph theory, a branch of theoretical chemistry, offers powerful tools for understanding ...read more
Photoswitches for Molecular Recognition
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