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:

Sharma Aditi1,Kaur Gurpreet1,Singh Diksha2,Gupta Vivek Kumar3,Banerjee Bubun1

Affiliation:

1. Department of Chemistry, Akal University, Talwandi Sabo, Bathinda, Punjab-151302, India

2. Department of Chemistry, Indus International University, V.P.O Bathu, Dist. Una, Himachal Pradesh, Pin-174301, India

3. Department of Physics, University of Jammu, Jammu Tawi-180 006, India

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.

Publisher

Bentham Science Publishers Ltd.

Subject

Organic Chemistry,Analytical Chemistry,Catalysis

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