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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
a   Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, ROC
,
Tamilselvan Duraisamy
a   Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, ROC
,
Alageswaran Jayaram
a   Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, ROC
,
Gopal Chandru Senadi
b   Department of Chemistry, Faculty of Engineering and Technology SRM Institute of Science and Technology, Kattankulathur, Tamilnadu – 603203, India
,
Wei-Yu Lin  ∗
a   Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, ROC
c   Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 80708, Taiwan, ROC
d   Drug Development and Value Creation Research Centre, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, ROC
› Author AffiliationsThe authors gratefully acknowledge funding from the Ministry of Science and Technology, Taiwan (MOST 109-2113-M-037-013) and Kaohsiung Medical University Research Foundation (KMU-M109004).
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1667-3977.
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Publication History

Received: 13 July 2021

Accepted after revision: 12 October 2021

Accepted Manuscript online:
12 October 2021

Article published online:
17 November 2021

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