Selective Aza Diels–Alder and Domino [4+2]/[2+2] Cycloaddition Reactions of Arynes with N-Sulfonyl Ketimines

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• 作者：I. N. Chaithanya Kiran ; R. Santhosh Reddy ; Chandraiah Lagishetti ; Huacheng Xu ; Zhen Wang ; Yun He
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：February 3, 2017
• 年：2017
• 卷：82
• 期：3
• 页码：1823-1832
• 全文大小：578K
• ISSN：1520-6904

文摘

Transition-metal-free inverse electron-demand aza Diels–Alder and domino [4+2]/[2+2] cycloaddition reaction of arynes and N-sulfonyl ketimines has been demonstrated. This novel, mild, and efficient protocol allows rapid access to isothiazole dioxide-fused dihydroquinoline or dihydrocyclobutaquinoline derivatives selectively by simply varying the equivalents of aryne precursors. The application of this method has been amply illustrated in the synthesis of 2,4-diarylquinolines.