4.8 Article

Conjugated Dienyne-Imides as Robust Precursors of 1-Azatrienes for 6 Electrocyclizations to Furo[2,3-b]dihydropyridine Cores

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 19, Pages 5482-5486

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201800303

Keywords

conjugation; electrocyclic reactions; heterocycles; palladium; synthetic methods

Funding

  1. National Natural Science Foundation of China [21572199, 21372196]

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A novel strategy to generate functionalized 1-azatriene intermediates for 6 electrocyclizations was developed by using readily accessible dienyne-imides and various terminal olefins under Pd-II catalysis. Taking advantage of the sequential cooperation between preloaded and incorporated functional handles at 1,3-dien-5-yne skeletons, this method not only enables the selective generation of putative 1-azatrienes but significantly accelerates their thermal 6-electrocyclic ring-closure processes to a series of highly substituted furo[2,3-b]dihydropyridine derivatives in good yields.

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