L-Cysteine Catalyzed Environmentally Benign One-pot Multicomponent Approach Towards the Synthesis of Dihydropyrano[2,3-c]pyrazole Derivatives

Author(s): Sana Sikandar, Ameer Fawad Zahoor*, Sajjad Ahmad, Muhammad Naveed Anjum, Mirza Nadeem Ahmad, Muhammad Sami Ullah Shah

Journal Name: Current Organic Synthesis

Volume 17 , Issue 6 , 2020

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Graphical Abstract:


Background: The pyrano[2,3-c]pyrazole derivatives are important building blocks of many biologically active compounds owing to their diverse biological potential for example, anti-inflammatory, anticancer, anti-microbial and anti-oxidant properties.

Objective: Keeping in mind the wide range of applications of pyrano[2,3-c]pyrazoles, herein we intended to develop a novel synthetic methodology for dihydropyranopyrazoles. We were also interested in determining the influence of amino acids and dipeptides as a catalyst on the synthesis of pyrano[2,3-c]pyrazole derivatives.

Methods: To achieve our objectives, we used a one-pot multi-component reaction of ethyl 3-oxobutanoate, propanedinitrile, hydrazine monohydrate and several substituted benzaldehydes by using different catalysts and solvents to synthesize our desired products in the presence of various catalysts.

Results and Discussion: We found that optimal conditions for the preparation of pyrano[2,3-c]pyrazoles were L-cysteine (0.5 mol) in the presence of water:ethanol (9:1) at 90 °C. Various 1,4-dihydropyrano[2,3- c]pyrazoles were afforded by using several substituted benzaldehydes in 66-97% yields.

Conclusion: We described a green and environmentally benign method to synthesize pyrano[2,3-c]pyrazoles in a one-pot four component reaction of ethyl 3-oxobutanoate, propanedinitrile, hydrazine monohydrate and different substituted benzaldehyde in the presence of L-cysteine in aqueous ethanol (9:1) at 90 °C. Excellent yields of the products, simple work-up, easily available starting materials, use of green solvents, naturally occurring catalyst, non-toxicity, non-chromatographic purification and environmentally benign reaction conditions are some main advantages of this protocol.

Keywords: Multicomponent reaction, L-cysteine, organocatalyst, green chemistry, 1, 4-dihydropyrano[2, 3-c]pyrazole, anti-oxidant properties.

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Year: 2020
Published on: 24 September, 2020
Page: [457 - 463]
Pages: 7
DOI: 10.2174/1570179417666200511092332
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