☆ 4.7 Article

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

JOURNAL OF ORGANIC CHEMISTRY (2017)

Journal

JOURNAL OF ORGANIC CHEMISTRY

Volume 82, Issue 3, Pages 1823-1832

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/acs.joc.6b02667

Keywords

-

Categories

Chemistry, Organic

Funding

National Science Foundation of China [21572027, 21602023, 21372267]
Chongqing Research and Frontier Technology [cstc2016jcyjA0403]
[2014M562278]
[Xm2014002]

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Abstract

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.

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