SLS-catalyzed Multi-component One-pot Reactions for the Convenient Synthesis of Spiro[indoline-3,4’-pyrano [2,3-c]pyrazole] Derivatives

Author(s): Archana Dhakar*, Archana Rajput, Ghazala Khanum, Dau D. Agarwal

Journal Name: Current Organocatalysis

Volume 8 , Issue 2 , 2021


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Graphical Abstract:


Abstract:

Background and Objective: Spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives are an important heterocyclic compounds. These compounds shows wide range of biological properties and exhibits varied pharmaceutical applications. Pyranopyrazoles, which are basically fused heterocyclic compounds and act as vasodilators, hypertensive, hypoglycaemic and anticancer agents.

Methods: An efficient and micelle-promoted surfactant catalyzed synthesis of spiro[indoline- 3,4′-pyrano[2,3-c]pyrazole] derivatives have been achieved via one-pot four-component reaction of hydrazine hydrate (phenyl hydrazine), ethyl acetoacetate, malononitrile (ethyl cyanoacetate) and isatin under thermal conditions (at 60°C) in water as a solvent.

Results: Sodium lauryl sulphate (SLS) used has been found to be an efficient and green catalyst. The compounds reported during this work were obtained in excellent yield, in a short duration of time and ease of work up. They were purified by recrystalization from ethanol and also the synthesized compounds were characterized by various spectroscopic techniques.

Conclusion: The method offers several advantages such as safe, cost-effective and catalyst easily recovered and reused for a minimum of five cycles, that confirms its good stability. Short reaction times, high yield and usage of eco-friendly catalyst and solvent are the key features of this methodology.

Keywords: Sodium lauryl sulphate (SLS), multicomponent reaction, isatin, malononitrile, ethyl acetoacetate, hydrazine hydrate.

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VOLUME: 8
ISSUE: 2
Year: 2021
Published on: 09 September, 2020
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DOI: 10.2174/2213337207999200910103325
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