An efficient synthesis of spiroacridinone derivatives from the facile reaction of isatins,dimedone, and 5-aminoindazole (6-aminoindazole or 5-aminoindole) |
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| Authors: | Wen-Ting Zhang Jian Sun Hong Zhu Rui-Xue Yue Yi Zhang Fu-Xiang Niu Liangce Rong |
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| Institution: | 1. Xuzhou Institute of Agricultural Sciences in Xuhuai Region of Jiangsu/Sweet Potato Research Institute, Chinese Academy of Agricultural Sciences, Xuzhou, China
Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, China;2. Xuzhou Institute of Agricultural Sciences in Xuhuai Region of Jiangsu/Sweet Potato Research Institute, Chinese Academy of Agricultural Sciences, Xuzhou, China;3. Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, China |
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| Abstract: | We have developed a simple and facil protocol for the synthesis of tetrahydrospiro(indoline-3,11′-pyrazolo4,3-a]acridine)-2,10′(7′H)-dione, tetrahydrospiro(indoline-3, 11′-pyrazolo3,4-a]acridine)-2,10′(7′H)-dione, and tetrahydrospiro (indoline-3,11′-pyrrolo3,2-a]acridine)-2,10′(7′H)-dione via PTSA·H2O-induced cyclization reaction from isatins, dimedone, and 5-aminoindazole (6-aminoindazole or 5-aminoindole) in mixed solvent (EtOH and CH3CN). In this research, 5-aminoindazole, 6-aminoindazole, and 5-aminoindole were effectively used to react with isatins and dimedone to give spiroacridinone derivatives. The advantages of this method are mild conditions, convenient manipulation, high yields, and a wide range of substrates. |
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