A facile synthesis of pyridoquinazolinones has been accomplished via C(sp)-H functionalization and annulation of benzoic acids with 2-aminopyridines using Cu(OAc) as catalyst in DMSO. The reaction involves the formation of amides which on amination followed by -amidation afford a wide array of products under ligand/base-free conditions.
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A Copper-Catalyzed Synthesis of Pyridoquinazolinones via C(sp)-H Functionalization and Annulation of Benzoic Acids with 2-Aminopyridines.
Org Lett
December 2024
Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi 221005, India.
A facile synthesis of pyridoquinazolinones has been accomplished via C(sp)-H functionalization and annulation of benzoic acids with 2-aminopyridines using Cu(OAc) as catalyst in DMSO. The reaction involves the formation of amides which on amination followed by -amidation afford a wide array of products under ligand/base-free conditions.
View Article and Find Full Text PDFTfO-mediated [4+2]-annulation of anthranils with 2-chloropyridines: enabling access to pyridoquinazolinones and euxylophoricine B.
Chem Commun (Camb)
July 2024
Department of Biological and Synthetic Chemistry, Center of Biomedical Research (CBMR), SGPGIMS Campus, Raibareli Road, Lucknow, UP 226014, India.
We present an efficient approach for synthesizing pyridoquinazolinones in the presence of triflic anhydride utilizing anthranils and 2-chloropyridines as starting materials. In this process, TfO initially activates anthranils forming an electrophilic 1-((trifluoromethyl)sulfonyl)benzo[]isoxazol-1-ium species. This species undergoes an annulation reaction with 2-chloropyridines, resulting in therapeutically useful pyridoquinazolinones.
View Article and Find Full Text PDFSerendipitous Synthesis of Pyridoquinazolinones an Oxidative C-C Bond Cleavage.
J Org Chem
June 2020
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
A direct one-pot copper-catalyzed oxidative C-C bond cleavage route to the synthesis of pyridoquinazolinones is described. This one-pot strategy involves a copper-catalyzed C-N coupling followed by concomitant C(sp)-H oxidation and amidation oxidative C-C bond cleavage under an O atmosphere to deliver the target molecules in high yields.
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