A violet-light-induced ring-opening of anthranils with chlorodiazirines has been developed. The metal-free protocol provides a rapid and efficient approach to -(2-carbonylaryl)benzamides in moderate to good yields under mild conditions. The reaction appears to involve α-chlorocarbenes, which trigger the ring-opening of anthranils.
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Violet-Light-Induced Ring-Opening of Anthranils with Chlorodiazirines.
Org Lett
January 2025
College of Chemistry and Molecular Sciences, Henan University, Kaifeng 475004, P. R. China.
A violet-light-induced ring-opening of anthranils with chlorodiazirines has been developed. The metal-free protocol provides a rapid and efficient approach to -(2-carbonylaryl)benzamides in moderate to good yields under mild conditions. The reaction appears to involve α-chlorocarbenes, which trigger the ring-opening of anthranils.
View Article and Find Full Text PDFRegioselective Brønsted Acid-Catalyzed Annulation of Cyclopropane Aldehydes with '-Aryl Anthranil Hydrazides: Domino Construction of Tetrahydropyrrolo[1,2-]quinazolin-5(1)ones.
J Org Chem
March 2020
Department of Chemistry, Indian Institute of Technology Ropar, Nangal Road, Rupnagar, Punjab 140001, India.
A highly regioselective synthesis of tetrahydropyrrolo1,2-]uinazolin-5(1)one derivatives was achieved by reacting cyclopropane aldehydes with '-aryl anthranil hydrazides in the presence of -toluene sulfonic acid (PTSA). The transformation involves domino imine formation and intramolecular cyclization to form 2-arylcyclopropyl-2,3-dihydroquinolin-4(1)-one, followed by nucleophilic ring opening of the cyclopropyl ring to form desired tetrahydropyrrolo[1,2-]quinazolin-5(1)one in good to excellent yield with complete regioselectivity. This protocol tolerates a great variety of functional groups and thus provides a simple and step-efficient method for pyrroloquinazolinone synthesis.
View Article and Find Full Text PDFCopper-Catalyzed Ring-Opening/Reconstruction of Anthranils with Oxo-Compounds: Synthesis of Quinoline Derivatives.
J Org Chem
October 2019
The Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Pharmaceutical Sciences , Jiangnan University, Lihu Avenue 1800 , Wuxi 214122 , P. R. China.
A copper-catalyzed protocol for the construction of various 2-aryl(alkyl)-3-acylquinolines or 3-arylquinolines using readily available anthranils and 1,3-diketones or aldehydes as starting materials is reported herein. Dioxygen as the sole oxidant and hexafluoroisopropanol as the solvent play an important role in both procedures. This ring-opening/reconstruction strategy involving N-O bond cleavage and C-N/C-C bond formation features high yields and broad substrate scope.
View Article and Find Full Text PDFGold-Catalyzed Regiospecific C-H Annulation of o-Ethynylbiaryls with Anthranils: π-Extension by Ring-Expansion En Route to N-Doped PAHs.
Angew Chem Int Ed Engl
June 2018
Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
We describe a novel, short, and flexible approach to diverse N-doped polycyclic aromatic hydrocarbons (PAHs) through gold-catalyzed π-extension of anthranils with o-ethynylbiaryls as reagents. This strategy uses easily accessible starting materials, is simple due to high step and atom economy, and shows good functional-group compatibility as well as scale-up potential. Mechanistically, the tandem reaction is proposed to involve a nucleophilic addition/ring opening/regiospecific C-H annulation/protodeauration sequence terminated by a Friedel-Crafts-type cyclization.
View Article and Find Full Text PDFLewis acid catalyzed diastereoselective [3+4]-annulation of donor-acceptor cyclopropanes with anthranils: synthesis of tetrahydro-1-benzazepine derivatives.
Chem Commun (Camb)
July 2017
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
A Lewis acid catalyzed [3+4]-annulation reaction between cyclopropane 1,1-diesters and anthranils has been developed. This annulation consists of a reaction sequence involving ring-opening/aromatization/nucleophilic addition. Thereinto, aromatization is the driving force for this annulation.
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