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DMAP-Catalyzed One-Pot Synthesis of Quinazoline-2,4-diones from 2-Aminobenzamides and Di-tert-butyl Dicarbonate.

ABSTRACT: The one-pot synthesis of quinazoline-2,4-diones was developed in the presence of 4-dimethylaminopyridine (DMAP) by metal-free catalysis. The commercially available (Boc)2O acted as a key precursor in the construction of the 2-position carbonyl of quinazolinediones. The p-methoxybenzyl (PMB)-activated heterocyclization could smoothly proceed at room temperature instead of the microwave condition. This strategy is compatible with a variety of substrates with different functional groups. Furthermore, this protocol was utilized to smoothly prepare Zenarestat with a total yield of 70%.

SUBMITTER: Chen H 

PROVIDER: S-EPMC7191844 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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DMAP-Catalyzed One-Pot Synthesis of Quinazoline-2,4-diones from 2-Aminobenzamides and Di-<i>tert</i>-butyl Dicarbonate.

Chen Hui H   Li Peng P   Qin Rongfei R   Yan Hong H   Li Gang G   Huang Haihong H  

ACS omega 20200416 16

The one-pot synthesis of quinazoline-2,4-diones was developed in the presence of 4-dimethylaminopyridine (DMAP) by metal-free catalysis. The commercially available (Boc)<sub>2</sub>O acted as a key precursor in the construction of the 2-position carbonyl of quinazolinediones. The <i>p</i>-methoxybenzyl (PMB)-activated heterocyclization could smoothly proceed at room temperature instead of the microwave condition. This strategy is compatible with a variety of substrates with different functional  ...[more]

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