Regioselective Brønsted Acid-Catalyzed Annulation of Cyclopropane Aldehydes with N′-Aryl Anthranil Hydrazides: Domino Construction of Tetrahydropyrrolo[1,2- a]quinazolin-5(1 H)ones Article

Singh, P, Kaur, N, Banerjee, P. (2020). Regioselective Brønsted Acid-Catalyzed Annulation of Cyclopropane Aldehydes with N′-Aryl Anthranil Hydrazides: Domino Construction of Tetrahydropyrrolo[1,2- a]quinazolin-5(1 H)ones . JOURNAL OF ORGANIC CHEMISTRY, 85(5), 3393-3406. 10.1021/acs.joc.9b03170

cited authors

  • Singh, P; Kaur, N; Banerjee, P

authors

abstract

  • A highly regioselective synthesis of tetrahydropyrrolo[1,2-a]quinazolin-5(1H)one derivatives was achieved by reacting cyclopropane aldehydes with N′-aryl anthranil hydrazides in the presence of p-toluene sulfonic acid (PTSA). The transformation involves domino imine formation and intramolecular cyclization to form 2-arylcyclopropyl-2,3-dihydroquinolin-4(1H)-one, followed by nucleophilic ring opening of the cyclopropyl ring to form desired tetrahydropyrrolo[1,2-a]quinazolin-5(1H)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.

publication date

  • March 6, 2020

published in

Digital Object Identifier (DOI)

start page

  • 3393

end page

  • 3406

volume

  • 85

issue

  • 5