Carbonylation of Anthranilic Acid with Aryl and Heteroaryl Bromides to Synthesize Benzoxazinone Derivatives

A simple and efficient, PdCl2(PhCN)2/P(tBu)3⋅HBF4‐catalyzed carbonylative cyclization of anthranilic acid with aryl bromide was investigated for the synthesis of benzoxazinones under mild reaction conditions. The developed protocol has been extended for the synthesis of quinazolin‐4(3 H)‐ones. Furthermore, the tolerance of a wide range of functional groups on anthranilic acid as well as on aryl bromide demonstrates the practical utility of the protocol.Three in 1: A simple and efficient PdCl2(PhCN)2/P(tBu)3⋅HBF4‐catalyzed carbonylative cyclization of anthranilic acid with aryl bromide was investigated for the synthesis of benzoxazinones under mild reaction conditions.Peer Reviewedhttps://deepblue.lib.umich.edu/bitstream/2027.42/137223/1/ajoc201600253.pdfhttps://deepblue.lib.umich.edu/bitstream/2027.42/137223/2/ajoc201600253-sup-0001-misc_information.pdfhttps://deepblue.lib.umich.edu/bitstream/2027.42/137223/3/ajoc201600253_am.pd

Expedient synthesis of an atypical oxazolidinone compound library

In order to address the current downturn in the drug discovery pipeline, initiatives are being undertaken to synthesise screening libraries of sp3-rich, low molecular weight compounds. As part of the European Lead Factory initiative, the synthesis and derivatisation of a simple hexahydrooxazolo[5,4-c]pyridin-2(1H)-one bicyclic carbamate has been achieved. The synthetic route employed involved a telescoped hetero-Diels-Alder/[2,3]-sigmatropic rearrangement/cyclisation sequence to deliver the desired core scaffold containing two points for further diversification. When applied, this synthesis was found to be robust and scalable which allowed the production of a 155 compound library