Synthesis of Aroylguanidines by an Unexpected Demethylation–Addition Cascade

Ling Hui Gu; Zhen Guo; Ling He; Qing Rong Qi

doi:10.1055/s-0033-1338511

Synthesis, Table of Contents

Synthesis 2013; 45(18): 2533-2544
DOI: 10.1055/s-0033-1338511

paper

Synthesis of Aroylguanidines by an Unexpected Demethylation–Addition Cascade

Ling Hui Gu

Key Laboratory of Drug-Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, Sichuan, 610041, P. R. of China Fax: +86(28)85501613 Email: qiqingronghh@yahoo.com.cn

,

Zhen Guo*

Key Laboratory of Drug-Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, Sichuan, 610041, P. R. of China Fax: +86(28)85501613 Email: qiqingronghh@yahoo.com.cn

,

Ling He

Key Laboratory of Drug-Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, Sichuan, 610041, P. R. of China Fax: +86(28)85501613 Email: qiqingronghh@yahoo.com.cn

,

Qing Rong Qi*

Key Laboratory of Drug-Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, Sichuan, 610041, P. R. of China Fax: +86(28)85501613 Email: qiqingronghh@yahoo.com.cn

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Abstract

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Abstract

A simple and efficient method was developed for the synthesis of N-aroyl-N′-arylguanidines under mild conditions by an unexpected demethylation–addition cascade reaction of readily available N-cyanoimidates with aryl amines. Moreover, 1-aryl-2-aminoquinazolin-4(1H)-ones and 2-(arylamino)quinazolin-4(3H)-ones can also be prepared by selective cyclization reactions of (2-fluorobenzoyl)- or (2-nitrobenzoyl)guanidines, respectively. This method provided two attractive strategies for the preparation 2-aminoquinazolinones derivatives from inexpensive reactants.

Key words

heterocycles - cyclizations - cascade reactions - amines - quinazolines - ketones

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References

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