- Synthetic applications of Pd(II)-catalyzed C-H carboxylation and mechanistic insights: Expedient routes to anthranilic acids, oxazolinones, and quinazolinones
-
A Pd(II)-catalyzed reaction protocol for the carboxylation of ortho-C-H bonds in anilides to form N-acyl anthranilic acids has been developed. This reaction procedure provides a novel and efficient strategy for the rapid assembly of biologically and pharmaceutically significant molecules, such as benzoxazinones and quinazolinones, from simple anilides without installing and removing an external directing group. The reaction conditions are also amenable to the carboxylation of N-phenyl pyrrolidinones. A monomeric palladacycle containing p-toluenesulfonate as an anionic ligand has been characterized by X-ray crystallography, and the crucial role of p-toluenesulfonic acid in the activation of C-H bonds in the presence of carbon monoxide is discussed. Identification of two key intermediates, a mixed anhydride and benzoxazinone formed by reductive elimination from organometallic Ar(CO)Pd(II)-OTs species, provides mechanistic evidence for a dual-reaction pathway.
- Giri, Ramesh,Lam, Jonathan K.,Yu, Jin-Quan
-
supporting information; experimental part
p. 686 - 693
(2010/03/25)
-
- Parallel synthesis and spectroscopic analysis of a collection of heterocycles based on the diazabenz[e]aceanthrylene core structure
-
A practical strategy for the synthesis of diazabenz[e]aceanthrylene-based heterocycles is reported. The key step in this approach is a microwave-assisted condensation and cyclisation reaction between an anthranilic acid derivative and a 2′-carbomethoxy substituted N-aryl lactam. The scope of the reaction has been explored as a function of both the nature and position of substituents in both components and variations in lactam ring size. Interesting structural and spectroscopic variations observed across the compound collection are described and explored using NMR, X-ray crystallography and computational techniques.
- Jones, Alan M.,Lebl, Tomas,Patterson, Stephen,van Mourik, Tanja,Früchtl, Herbert A.,Philp, Douglas,Slawin, Alexandra M.Z.,Westwood, Nicholas J.
-
supporting information; experimental part
p. 563 - 578
(2009/04/06)
-
- Synthesis of a new family of N-aryl lactams active on chemesthesis and taste
-
A new class of synthetic compounds with chemesthetic activity has been identified. They have been designed ex-novo by structural similarity with known cooling compounds such as menthol, icilin and cyclic ketoenamines. 19 new derivatives have been obtained
- Bassoli, Angela,Borgonovo, Gigliola,Busnelli, Gilberto,Morini, Gabriella
-
p. 1656 - 1663
(2007/10/03)
-