Cascade Nitration/Cyclization of 1,7‐Enynes with <i>t</i>BuONO and H₂O: One‐Pot Self‐Assembly of Pyrrolo[4,3,2‐<i>de</i>]quinolinones

Abstract

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).