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Current Organocatalysis

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ISSN (Print): 2213-3372
ISSN (Online): 2213-3380

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Research Article

A General Method for the Synthesis of 11H-Indeno[1,2-B]Quinoxalin- 11-Ones and 6H-Indeno[1,2-B]Pyrido[3,2-E]Pyrazin-6-One Derivatives Using Mandelic Acid as an Efficient Organo-catalyst at Room Temperature

Author(s): Aditi Sharma, Gurpreet Kaur, Diksha Singh, Vivek Kumar Gupta and Bubun Banerjee*

Volume 9, Issue 1, 2022

Published on: 25 August, 2021

Page: [53 - 61] Pages: 9

DOI: 10.2174/2213337208666210825112301

Price: $65

Abstract

Aims: Synthesis of 11H-indeno[1,2-b]quinoxalin-11-ones as well as 6H-indeno[ 1,2-b]pyrido[3,2-e]pyrazin-6-one derivatives under greener conditions.

Background: Quinoxaline and related skeletons are very common in naturally occurring bioactive compounds.

Objective: Design a facile, green and organo-catalyzed method for the synthesis of 11H-indeno[ 1,2-b]quinoxalin-11-ones as well as 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one derivatives.

Methods: Both the scaffolds were synthesized via the condensation of ninhydrin and o-phenylenediamines or pyridine-2,3-diamines respectively by using a catalytic amount of mandelic acid as an efficient, commercially available, low cost, organo-catalyst in aqueous ethanol at room temperature.

Results: Mild reaction conditions, use of metal-free organocatalyst, non-toxic solvent, ambient temperature, and no column chromatographic separation are some of the notable advantages of our developed protocol.

Conclusion: In conclusion, we have developed a simple, mild, facile and efficient method for the synthesis of structurally diverse 11H-indeno[1,2-b]quinoxalin-11-one derivatives via the condensation reactions of ninhydrin and various substituted benzene-1,2-diamines using a catalytic amount of mandelic acid as a commercially available metal-free organo-catalyst in aqueous ethanol at room temperature. Under the same optimized reaction conditions, synthesis of 6H-indeno[ 1,2-b]pyrido[3,2-e]pyrazin-6-one derivatives was also accomplished with excellent yields by using pyridine-2,3-diamines instead of o-phenylenediamine.

Keywords: Mandelic acid, 11H-indeno[1, 2-b]quinoxalin-11-ones, 6H-indeno[1, 2-b]pyrido[3, 2-e]pyrazin-6-ones, sustainable organocatalyst, ninhydrin, organocatalysis.

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