Ultrasound-assisted rapid and efficient one-pot synthesis of furanyl spirooxindolo and spiroquinoxalinopyrrolizidines by 1,3-dipolar cycloaddition: a green protocol

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• 作者：Venkata Bharat Nishtala ; Jagadeesh Babu Nanubolu…
• 关键词：Ultrasonication ; 1 ; 3 ; Dipolar cycloaddition ; Azomethine ylide ; Spirooxindolopyrrolizidines ; Spiroquinoxalinopyrrolizidines ; Dipolarophile
• 刊名：Research on Chemical Intermediates
• 出版年：2017
• 出版时间：March 2017
• 年：2017
• 卷：43
• 期：3
• 页码：1365-1381
• 全文大小：
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Catalysis; Physical Chemistry; Inorganic Chemistry;
• 出版者：Springer Netherlands
• ISSN：1568-5675
• 卷排序：43

文摘

Efficient synthesis of novel spirooxindolo and spiroquinoxalinopyrrolizidine derivatives was expediently accomplished with regioselectivity via one-pot, three-component 1,3-dipolar cycloaddition using ultrasonication. Chalcones derived from both heteroaryl methyl ketones and furfural were used as dipolarophiles in these reactions. The synthesized compounds were analyzed by 1H and 13C nuclear magnetic resonance (NMR), mass spectrometry, and elemental (CHN) analysis. Single-crystal X-ray diffraction studies of one of the compounds (11d) proved the structure and regiochemistry of the cycloaddition. The ultrasound methodology is clearly advantageous, and the desired products were obtained in moderate to good yield in shorter reaction time compared with conventional heating and fusion methods.