Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 34, Pages 9017-9020Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201404192
Keywords
cascade reactions; cyclization; enynes; nitration; nitrogen heterocycles
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Funding
- Natural Science Foundation of China [21172060]
- Specialized Research Fund for the Doctoral Program of Higher Education [20120161110041]
- Hunan Provincial Natural Science Foundation of China [13JJ2018]
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Here we describe the one-pot construction of the pyrrolo[4,3,2-de] quinolinone scaffold by a cascade nitration/cyclization sequence of 1,7-enynes with tBuONO and H2O. The cascade proceeds through alkene nitration, 1,7-enyne 6-exo- trig cyclization, C-H nitrations, and redox cyclization, and exhibits excellent functional group tolerance. The mechanism was investigated using in situ high-resolution mass spectrometry (HR-MS).
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