Cascade Nitration/Cyclization of 1,7‐Enynes with tBuONO and H2O: One‐Pot Self‐Assembly of Pyrrolo[4,3,2‐de]quinolinones |
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| Authors: | Yu Liu Jia‐Ling Zhang Dr Ren‐Jie Song Peng‐Cheng Qian Prof Dr Jin‐Heng Li |
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| Institution: | 1. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China);2. State Key Laboratory of Applied Organic Chemistry Lanzhou University, Lanzhou 730000 (China) |
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| Abstract: | Here we describe the one‐pot construction of the pyrrolo4,3,2‐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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| Keywords: | cascade reactions cyclization enynes nitration nitrogen heterocycles |
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