Lactamization of sp2 C−H Bonds with CO2: Transition‐Metal‐Free and Redox‐Neutral
- 20 April 2016
- journal article
- research article
- Published by Wiley in Angewandte Chemie-International Edition
- Vol. 55 (25), 7068-7072
- https://doi.org/10.1002/anie.201602095
Abstract
The first direct use of carbon dioxide in the lactamization of alkenyl and heteroaryl C−H bonds to synthesize important 2‐quinolinones and polyheterocycles in moderate to excellent yields is reported. Carbon dioxide, a nontoxic, inexpensive, and readily available greenhouse gas, acts as an ideal carbonyl source. Importantly, this transition‐metal‐free and redox‐neutral process is eco‐friendly and desirable for the pharmaceutical industry. Moreover, these reactions feature a broad substrate scope, good functional group tolerance, facile scalability, and easy product derivatization.Keywords
Funding Information
- National Natural Science Foundation of China (21502124)
This publication has 75 references indexed in Scilit:
- Synthesis of phenanthridinones viapalladium-catalyzed C(sp2)–H aminocarbonylation of unprotected o-arylanilinesChemical Communications, 2013
- Carbon dioxide utilization with C–N bond formation: carbon dioxide capture and subsequent conversionEnergy & Environmental Science, 2012
- Transition-metal-catalyzed C–C bond formation through the fixation of carbon dioxideChemical Society Reviews, 2011
- Parallel Synthesis of Ureas and Carbamates from Amines and CO2 under Mild ConditionsOrganic Letters, 2010
- Synthesis and in vitro anti-hepatitis B virus activities of 4-aryl-6-chloro-quinolin-2-one and 5-aryl-7-chloro-1,4-benzodiazepine derivativesBioorganic & Medicinal Chemistry Letters, 2008
- Microwave-Assisted Multistep Synthesis of Functionalized 4-Arylquinolin-2(1H)-ones Using Palladium-Catalyzed Cross-Coupling ChemistryThe Journal of Organic Chemistry, 2005
- Synthesis Routes Towards the Farnesyl Protein Transferase Inhibitor ZARNESTRATMEuropean Journal of Organic Chemistry, 2004
- Kinetic and Computational Studies of a Novel Pseudopericyclic Electrocyclization. The First Evidence for Torquoselectivity in a 6-π SystemJournal of the American Chemical Society, 1997
- .omega.-[(4-Phenyl-2-quinolyl)oxy]alkanoic acid derivatives: a new family of potent LTB4 antagonistsJournal of Medicinal Chemistry, 1992
- 4-Phenyl-2-(1-piperazinyl)quinolines with potent antidepressant activity.CHEMICAL & PHARMACEUTICAL BULLETIN, 1980