Details

Autor(en) / Beteiligte

• Liu, Yu
• Zhang, Jia-Ling
• Song, Ren-Jie
• Qian, Peng-Cheng
• Li, Jin-Heng

Titel

Cascade Nitration/Cyclization of 1,7-Enynes with tBuONO and H2O: One-Pot Self-Assembly of Pyrrolo[4,3,2-de]quinolinones

Ist Teil von

• Angewandte Chemie (International ed.), 2014-08, Vol.53 (34), p.9017-9020

Auflage

International ed. in English

Ort / Verlag

Weinheim: WILEY-VCH Verlag

Erscheinungsjahr

2014

Link zum Volltext

Quelle

MEDLINE

Beschreibungen/Notizen

• 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). Nitration cascade: The pyrrolo[4,3,2‐de]quinolinone scaffold was synthesized by a metal‐free reaction of N‐(2‐(ethynyl)aryl)acrylamides, tert‐butyl nitrite and H2O. This cascade reaction is triggered by alkene nitration followed by 1,7‐enyne 6‐exo‐trig cyclization, CH nitrations, and redox cyclization and forms the product in good yields.