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The Aryne aza-Diels-Alder Reaction: Flexible Syntheses of Isoquinolines

Abstract : Two cascade reactions have been developed for the time-efficient preparation of a variety of functionalized aromatic heterocyclic products exhibiting an isoquinoline core. The approach is based on the normal electron-demand [4 + 2] aza-Diels−Alder cycloaddition of electron-rich N-aryl imines with arynes. Using this strategy, an expeditious total synthesis of the naturally occurring benzo[c]phenanthridine alkaloid nornitidine was achieved.
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https://hal.archives-ouvertes.fr/hal-01224296
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Submitted on : Wednesday, November 4, 2015 - 2:54:40 PM
Last modification on : Tuesday, December 14, 2021 - 8:36:12 AM

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Juan-Carlos Castillo, Jairo Quiroga, Rodrigo Abonia, Jean Rodriguez, Yoann Coquerel. The Aryne aza-Diels-Alder Reaction: Flexible Syntheses of Isoquinolines. Organic Letters, American Chemical Society, 2015, 17, pp.3374. ⟨10.1021/acs.orglett.5b01704⟩. ⟨hal-01224296⟩

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