33986-96-8Relevant academic research and scientific papers
Regioselective Br?nsted Acid-Catalyzed Annulation of Cyclopropane Aldehydes with N′-Aryl Anthranil Hydrazides: Domino Construction of Tetrahydropyrrolo[1,2- a]quinazolin-5(1 H)ones
Banerjee, Prabal,Kaur, Navpreet,Singh, Priyanka
, p. 3393 - 3406 (2020)
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.
Copper-catalyzed efficient synthesis of 5-arylindazolo[3,2-b]quinazolin-7(5H)-ones from 2-nitrobenzaldehydes
Arasteh Fard, Zahra,Dilmaghani, Karim Akbari,Soheilizad, Mehdi,Larijani, Bagher,Mahdavi, Mohammad
, p. 2197 - 2201 (2018/03/28)
A novel and practical copper-catalyzed approach was developed for the preparation of 5-arylindazolo[3,2-b]quinazolin-7(5H)-ones. The 2-amino-N′-arylbenzohydrazideis easily prepared by a reaction of isatoic anhydride with arylhydrazine. Then, through a con
Synthesis of Novel Phthalazino[1,2-b]quinazolinedione Derivatives: Efficient and Practical Reaction of 2-Amino-N′-Arylbenzohydrazides and 2-Formylbenzoic Acids
Arasteh-Fard, Zahra,Dilmaghani, Karim Akbari,Saeedi, Mina,Mahdavi, Mohammad,Shafiee, Abbas
, p. 539 - 542 (2016/07/21)
This work reported the synthesis of novel phthalazino[1,2-b]quinazolinedione derivatives through the reaction of 2-amino-N′-arylbenzohydrazides and 2-formylbenzoic acids in the presence of TsOH in EtOH under reflux conditions.
Substrate Controlled Synthesis of Benzisoxazole and Benzisothiazole Derivatives via PhI(OAc)2-Mediated Oxidation Followed by Intramolecular Oxidative O-N/S-N Bond Formation
Anand, Devireddy,Patel, Om P. S.,Maurya, Rahul K.,Kant, Ruchir,Yadav, Prem P.
, p. 12410 - 12419 (2016/01/09)
A phenyliodine(III) diacetate (PIDA)-mediated, highly efficient and tandem approach for the synthesis of aryldiazenylisoxazolo(isothiazolo)arenes from simple 2-amino-N′-arylbenzohydrazides has been developed. The reaction proceeds via formation of (E)-(2-aminoaryl)(aryldiazenyl)methanone as the key intermediate, followed by intramolecular oxidative O-N/S-N bond formation in one pot at room temperature. The quiet different reactivity of the substrate is due to the formation of a diazo intermediate which encounters a nucleophilic attack by carbonyl oxygen on the electrophilic amine to produce isoxazole products, as compared to the previous reportsa,b,4 in which an N-acylnitrenium ion intermediate is intramolecularly trapped by an amine group.
