Abstract
A simple, highly efficient and green procedure for the condensation of aryl and alkyl 1,2diamines with α-diketones in the presence of catalytic amount of oxalic acid at room temperature is described. Using this method, quinoxaline derivatives as biologically interesting compounds are produced in high to excellent yields and short reaction times.
Highlights
The quinoxaline skeleton is a building block for the preparation of substances with pronounced biological activities, such as antimycobacterial,[1] antidepressant,[2] and antitumor drugs.[3]
As part of our ongoing program to develop more efficient and environmentally benign methods for organic transformations using economic and ecofriendly materials as catalysts and reagents,[14] we have looked into the synthesis of quinoxaline derivatives via the condensation of 1,2-diamines with α-diketones in the presence of catalytic amounts of oxalic acid at room temperature (Scheme 1)
In order to find a suitable catalyst for the synthesis of quinoxalines from 1,2-diamines and αdiketones, the condensation of benzene-1,2-diamine with benzil was chosen as a model to provide compound 3a (Scheme 1), and its behavior was studied in the presence of various catalysts in EtOH/H2O at room temperature
Summary
The quinoxaline skeleton is a building block for the preparation of substances with pronounced biological activities, such as antimycobacterial,[1] antidepressant,[2] and antitumor drugs.[3]. As part of our ongoing program to develop more efficient and environmentally benign methods for organic transformations using economic and ecofriendly materials as catalysts and reagents,[14] we have looked into the synthesis of quinoxaline derivatives via the condensation of 1,2-diamines with α-diketones in the presence of catalytic amounts of oxalic acid at room temperature (Scheme 1).
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