15089-80-2Relevant articles and documents
Synthetic applications of Pd(II)-catalyzed C-H carboxylation and mechanistic insights: Expedient routes to anthranilic acids, oxazolinones, and quinazolinones
Giri, Ramesh,Lam, Jonathan K.,Yu, Jin-Quan
supporting information; experimental part, p. 686 - 693 (2010/03/25)
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.
Process for preparing pyrimidine derivatives
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, (2008/06/13)
The present invention provides a process for preparing a 5,6-dihydro-3H-pyrimidin-4-one derivatives which comprises the steps of (a) dehydrating a N-acyl beta amino acid in the presence of a dehydration agent and an organic solvent for a sufficient period of time and under suitable temperature and pressure conditions to form an oxazone (b) adding a carboxylic acid and a primary amine salt of a carboxylic acid to said oxazone to form a mixture, (c) distilling azeotropically said mixture for a suitable period of time and under suitable temperature and pressure conditions to substantially remove said dehydration agent and said organic solvent, and (d) heating the product of step (c) for a sufficient period of time and under suitable temperature and pressure conditions to form said pyrimidin derivatives.