Download PDF
Synthesis 2014; 46(04): 510-514
DOI: 10.1055/s-0033-1340470
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 3,4,5-Trisubstituted Isoxazoles by the 1,3-Dipolar Cycloaddition Reaction of α-Azido Acrylates and Aromatic Oximes

Manman Hu
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P. R. of China   Fax: +86(553)5910126   Email: shyj@mail.ahnu.edu.cn
,
Xinwei He
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P. R. of China   Fax: +86(553)5910126   Email: shyj@mail.ahnu.edu.cn
,
Zhiqiang Niu
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P. R. of China   Fax: +86(553)5910126   Email: shyj@mail.ahnu.edu.cn
,
Zhenglei Yan
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P. R. of China   Fax: +86(553)5910126   Email: shyj@mail.ahnu.edu.cn
,
Fuyin Zhou
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P. R. of China   Fax: +86(553)5910126   Email: shyj@mail.ahnu.edu.cn
,
Yongjia Shang*
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P. R. of China   Fax: +86(553)5910126   Email: shyj@mail.ahnu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 23 October 2013

Accepted after revision: 25 November 2013

Publication Date:
02 January 2014 (online)

    Permissions and Reprints All articles of this category


Abstract

A novel, one-pot, cascade reaction sequence featuring the 1,3-dipolar cycloaddition reaction of α-azido acrylates and aromatic oximes was developed. This procedure provides an efficient, straightforward and metal-free method for the synthesis of 3,4,5-trisubstituted isoxazoles under mild reaction conditions.

Key words

1,3-dipolar cycloaddition - α-azido acrylates - aromatic oximes - isoxazoles - one-pot synthesis

Supporting Information

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

  • References

    • 1a Rajanarendar E, Shaik FP, Reddy AS. R. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2008; 47: 1753
    • 1b Rajanarendar E, Murthy KR, Reddy MN, Shaik FP. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2011; 50: 1658
  • 2 Rajanarendara E, Ramesha P, Srinivasa M, Shaik FP. Phosphorus, Sulfur Silicon Relat. Elem. 2009; 184: 733
    Crossref
  • 3 Batra S, Srinivasan T, Rastogi SK, Kundu B, Patra A, Bhaduri AP, Dixit M. Bioorg. Med. Chem. Lett. 2002; 12: 1905
    Crossref
  • 4 Hamama WS, Ibrahim ME, Zoorob HH. Synth. Commun. 2013; 43: 2393
    Crossref
  • 5 Kaur A, Singh B, Jaggi AS. Bioorg. Med. Chem. Lett. 2013; 23: 797
    Crossref
  • 6 Avupati VR, Kurre PN, Bagadi SR, Muthyala MK, Yejella RP. Chem-Bio. Inform. J. 2010; 10: 74
  • 7 Ueda M, Sato A, Ikeda Y, Miyoshi T, Naito T, Miyata O. Org. Lett. 2010; 12: 2594
    CrossrefPubMed
  • 8 She Z, Niu D, Chen L, Gunawan MA, Shanja X, Hersh WH, Chen Y. J. Org. Chem. 2012; 77: 3627
    Crossref
  • 9 Ueda M, Sugita S, Sato A, Miyoshi T, Miyata O. J. Org. Chem. 2012; 77: 9344
    Crossref
  • 10 Waldo JP, Mehta S, Neuenswander B, Lushington GH, Larock RC. J. Comb. Chem. 2008; 10: 658
    Crossref
  • 11 Gayon E, Quinonero O, Lemouzy S, Vrancken E, Campagne JM. Org. Lett. 2011; 13: 6418
    CrossrefPubMed
  • 12 Hong D, Chen Z.-B, Lin X.-F, Wang Y.-G. Org. Lett. 2010; 12: 4608
    Crossref
    • 13a Hong D, Zhu Y, Lin X, Wang Y. Tetrahedron 2011; 67: 650
      Crossref
    • 13b Ng EP. J, Wang Y.-F, Hui BW.-Q, Lapointe G, Chiba S. Tetrahedron 2011; 67: 7728
      Crossref
  • 14 Dinda BK, Jana AK, Mal D. Chem. Commun. 2012; 48: 3999
    Crossref
  • 15 The crystal data of compound 3i have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 940588. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk] or via www.ccdc.cam.ac.uk/data_request/cif. Compound 3i: space group P2(1)/c, a = 7.918(2) Å, b = 11.326(3) Å, c = 18.103(6) Å, α = 90°, β = 100.868°, γ = 90°, V = 1594.4(8) Å3, T = 293(2) K, Z = 4. More data are given in the Supporting Information.
  • 16 Zhu S.-R, Shi S.-H, Gerritz SW. Tetrahedron Lett. 2011; 52: 4001
    Crossref
  • 17 Li Y, Hong D, Lu P, Wang Y.-G. Tetrahedron Lett. 2011; 52: 4161
    Crossref