Copper-Catalyzed Oxidative Cyclization of 2-Aminobenzamide Derivatives: Efficient Syntheses of Quinazolinones and Indazolones

Karthick Govindan; Tamilselvan Duraisamy; Alageswaran Jayaram; Gopal Chandru Senadi; Wei-Yu Lin

doi:10.1055/a-1667-3977

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(04): 1115-1124
DOI: 10.1055/a-1667-3977

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Copper-Catalyzed Oxidative Cyclization of 2-Aminobenzamide Derivatives: Efficient Syntheses of Quinazolinones and Indazolones

Karthick Govindan

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, ROC

,

Tamilselvan Duraisamy

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, ROC

,

Alageswaran Jayaram

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, ROC

,

Gopal Chandru Senadi

^bDepartment of Chemistry, Faculty of Engineering and Technology SRM Institute of Science and Technology, Kattankulathur, Tamilnadu – 603203, India

,

Wei-Yu Lin ∗

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, ROC

^cDepartment of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 80708, Taiwan, ROC

^dDrug Development and Value Creation Research Centre, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, ROC

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Abstract

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Abstract

A simple copper-catalyzed assembly to formulate quinazolinone and indazolone derivatives in a single protocol manner is reported. These transformations are based on the fact that DMF can serve as a reaction solvent and one carbon synthon for the construction of heterocyclic rings. Moreover, this protocol features base-free and Brønsted acid free environmentally benign conditions with broad synthetic scope. A good scalability is demonstrated.

Key words

copper - catalysis - C₁ synthon - DMF - oxidative process - quinazolinone - indazolone

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