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Synthesis 2013; 45(3): 334-340
DOI: 10.1055/s-0032-1317945
paper
© Georg Thieme Verlag Stuttgart · New York

Selective Synthesis of Cyano-Functionalized 2-Aryl-4H-chromenes and 2-Amino-4H-chromene-3-carbonitriles by Catalyst-Tuned Reactions of 2-Hydroxychalcones with 2-Substituted Acetonitriles

Guodong Yin*
Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, College of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi 435002, P. R. of China   Fax: +86(714)6515602   eMail: gdyin@hbnu.edu.cn
,
Houqiang Shi
Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, College of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi 435002, P. R. of China   Fax: +86(714)6515602   eMail: gdyin@hbnu.edu.cn
,
Liqianyun Xu
Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, College of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi 435002, P. R. of China   Fax: +86(714)6515602   eMail: gdyin@hbnu.edu.cn
,
Xianhong Wei
Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, College of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi 435002, P. R. of China   Fax: +86(714)6515602   eMail: gdyin@hbnu.edu.cn
,
Qing Tao
Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, College of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi 435002, P. R. of China   Fax: +86(714)6515602   eMail: gdyin@hbnu.edu.cn
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Publikationsverlauf

Received: 24. Oktober 2012

Accepted after revision: 03. Dezember 2012

Publikationsdatum:
03. Januar 2013 (online)

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Abstract

A selective synthesis of 4H-chromenes by the reactions of 2-hydroxychalcone derivatives with acetonitriles substituted with electron-withdrawing groups is described. Under catalyst-free conditions, the reactions give cyano-functionalized 2-aryl-4H-chromenes, whereas in the presence of sodium bicarbonate, 2-amino-4H-chromene-3-carbonitriles are obtained in excellent yields.

Key words

heterocycles - nitriles - catalysis - chromenes

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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