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Cascade Nitration/Cyclization of 1,7‐Enynes with t BuONO and H 2 O: One‐Pot Self‐Assembly of Pyrrolo[4,3,2‐ de ]quinolinones
Author(s) -
Liu Yu,
Zhang JiaLing,
Song RenJie,
Qian PengCheng,
Li JinHeng
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201404192
Subject(s) - nitration , chemistry , alkene , cascade , enyne , medicinal chemistry , stereochemistry , sequence (biology) , combinatorial chemistry , organic chemistry , catalysis , chromatography , biochemistry
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 t BuONO and H 2 O. The cascade proceeds through alkene nitration, 1,7‐enyne 6‐ exo ‐trig cyclization, CH nitrations, and redox cyclization, and exhibits excellent functional group tolerance. The mechanism was investigated using in situ high‐resolution mass spectrometry (HR‐MS).