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Synlett 2013; 24(14): 1851-1855
DOI: 10.1055/s-0033-1339332
letter
© Georg Thieme Verlag Stuttgart · New York

Novel Synthesis of 3-Aryl-4-hydroxybenzofurans via Four-Component Reaction from Substituted Nitrostyrenes, Aromatic Aldehydes, Cyclohexan-1,3-diones, and Ammonium Acetate

Yan Li
a   School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China   Fax: +86(514)87975244   eMail: wangcd@yzu.edu.cn
,
Hui Liu
a   School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China   Fax: +86(514)87975244   eMail: wangcd@yzu.edu.cn
,
Liang Sun
b   Yancheng Orgunion Pharmaceutical Sci & Tech Co., Ltd., 39 Huanghe Road, Yancheng 224400, P. R. of China
,
Juanjuan Liu
a   School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China   Fax: +86(514)87975244   eMail: wangcd@yzu.edu.cn
,
Zhiheng Xue
a   School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China   Fax: +86(514)87975244   eMail: wangcd@yzu.edu.cn
,
Juan Yao
a   School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China   Fax: +86(514)87975244   eMail: wangcd@yzu.edu.cn
,
Cunde Wang*
a   School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China   Fax: +86(514)87975244   eMail: wangcd@yzu.edu.cn
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Publikationsverlauf

Received: 20. April 2013

Accepted after revision: 10. Juni 2013

Publikationsdatum:
30. Juli 2013 (online)

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Abstract

An one-pot-reaction methodology was developed to synthesize a variety of polysubstituted 3-aryl-2-arylmethylene amino-4-hydroxybenzofurans from substituted β-nitrostyrenes, aromatic aldehydes, ammonium acetate, and cyclohexane-1,3-diones for the generation of a wide range of structurally interesting and pharmacologically significant compounds. The reaction pathway involves Michael addition of substituted nitrostyrenes and cyclohexane-1,3-diones, then nucleophilic addition of 2-(2-nitro-1-phenylethyl)cyclohexane-1,3-dione and Schiff base generated from aromatic aldehyde and ammonium acetate and intramolecular cyclization, followed by dehydroaromatization to afford the corresponding 3-aryl-2-arylmethyleneamino-4-hydroxybenzofurans.

Key words

multicomponent reaction - 4-hydroxybenzofuran - substituted β-nitrostyrene - dehydroaromatization - cyclohexane-1,3-dione

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
  • Supporting Information
 

  • References and Notes

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