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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 10
226
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Original Articles

Facile and efficient synthesis of quinazoline-2,4(1H,3H)-diones through sequential hydrogenation condensation

, , , ORCID Icon & ORCID Icon
Pages 1183-1189 | Received 03 Dec 2017, Published online: 26 Mar 2018
 

ABSTRACT

The heterocyclizations from various methyl (2-nitrobenzoyl)carbamates to substituted quinazoline-2,4(1H,3H)-diones under hydrogenation conditions were investigated in this study. In the presence of p-toluenesulfonic acid monohydrate in methanol, various quinazoline-2,4(1H, 3H)-diones were obtained in good to excellent yields within 12 h. The reaction was proposed to proceed through the cascade reactions of nitro reduction and condensation.

GRAPHICAL ABSTRACT

Additional information

Funding

This work was supported by the National Natural Science Foundation of China under Grant 81703362; CAMS Innovation Fund for Medical Sciences under Grant CAMS-2016-I2M-1-010; and Fundamental Scientific Research Fund of Chinese Academy of Medical Sciences under Grant 2016ZX350030.

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