A new rapid multicomponent domino reaction for the formation of functionalized benzo[h]pyrazolo[3,4-b]quinolines |
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Authors: | Jiang Bo Zhang Ge Ma Ning Shi Feng Tu Shu-Jiang Kaur Parminder Li Guigen |
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Affiliation: | School of Chemistry and Chemical Engineering, Xuzhou Normal University, Jiangsu, PR China. |
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Abstract: | A new multicomponent domino reaction for rapid and regioselective synthesis of highly functionalized benzo[h]pyrazolo[3,4-b]quinolines has been established. The reaction can be conducted by using readily available and inexpensive substrates under microwave irradiation within short periods of 10-26 min. Good to excellent chemical yields (61-91%) and complete regioselectivity have been achieved for 22 examples. Tedious work-up procedure can be avoided due to the direct precipitation of products from the reaction solution. The resulting benzoquinolines have been readily converted into quinoxaline-fused benzo[h]isoxazolo[5,4-b]quinoline analogues by treating with benzene-1,2-diamine under microwave irradiation. The structural assignment has been ambiguously confirmed by X-ray analysis. A new mechanism has been proposed for this new multicomponent domino process. |
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