Synlett 2014; 25(16): 2293-2296
DOI: 10.1055/s-0034-1378977
cluster
© Georg Thieme Verlag Stuttgart · New York

Lewis Acid Catalyzed Intramolecular Ring-Opening of Triazole-Substituted Methylenecyclopropanes: An Approach to 4H-[1,2,3]Triazolopyrazines and 4H-[1,2,3]Triazolo[1,4]diazepines

Run Sun
a   Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Mei-Long Road, Shanghai 200237, P. R. of China
,
Di-Han Zhang
b   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China   Fax: +86(21)64166128   Email: mshi@mail.sioc.ac.cn
,
Min Shi*
a   Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Mei-Long Road, Shanghai 200237, P. R. of China
b   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China   Fax: +86(21)64166128   Email: mshi@mail.sioc.ac.cn
› Author Affiliations
Further Information

Publication History

Received: 27 May 2014

Accepted after revision: 28 July 2014

Publication Date:
08 September 2014 (online)


Abstract

A series of novel methylenecyclopropane-triazoles have been successfully prepared. Their intramolecular nucelophilic cyclizations have been explored in the presence of Yb(NTf2)3 catalyst, giving the corresponding triazole containing six- and seven-membered heterocycles in good yields upon heating in toluene.

Supporting Information

 
  • References


    • For the synthesis of MCP, please see:
    • 1a Brandi A, Goti A. Chem. Rev. 1998; 98: 589
    • 1b Audran G, Pellissier H. Adv. Synth. Catal. 2010; 352: 575
  • 2 Isaacs NS. Physical Organic Chemistry . John Wiley; New York: 1987: 283
  • 3 Small Ring Compounds in Organic Synthesis III. de Meijere A. Springer; Berlin: 1988

    • For selected reviews on MCP, see:
    • 4a Lautens M, Klute W, Tam W. Chem. Rev. 1996; 96: 49
    • 4b Binger P, Wedemann P, Kozhushkov SI, de Meijere A. Eur. J. Org. Chem. 1998; 113
    • 4c de Meijere A, Kozhushkov SI, Khlebnikov AF. Top. Curr. Chem. 2000; 207: 89
    • 4d Nakamura I, Yamamoto Y. Adv. Synth. Catal. 2002; 344: 111
    • 4e Yamago S, Nakamura E. Org. React. (N.Y.) 2002; 61: 1
    • 4f Nakamura E, Yamago S. Acc. Chem. Res. 2002; 35: 867
    • 4g Brandi A, Cicchi S, Cordero FM, Goti A. Chem. Rev. 2003; 103: 1213
    • 4h Shao LX, Shi M. Curr. Org. Chem. 2007; 11: 1135
    • 4i Rubin M, Rubina M, Gevorgyan V. Chem. Rev. 2007; 107: 3117
    • 4j Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
    • 4k Yu L, Guo R. Org. Prep. Proced. Int. 2011; 43: 209
    • 4l Shi M, Lu JM, Wei Y, Shao LX. Acc. Chem. Res. 2012; 45: 641
    • 4m Zhang DH, Tang XY, Shi M. Acc. Chem. Res. 2014; 47: 913
    • 4n Jiao L, Yu Z.-X. J. Org. Chem. 2013; 78: 6842
    • 4o Mack DJ, Njardarson JT. ACS Catal. 2013; 3: 272
    • 6a Lautens M, Han W, Liu JH. C. J. Am. Chem. Soc. 2003; 125: 4028
    • 6b Scott ME, Schwarz CA, Lautens M. Org. Lett. 2006; 8: 5521
    • 6c Scott ME, Bethuel Y, Lautens M. J. Am. Chem. Soc. 2007; 129: 1482
    • 7a Ma SM, Zhang JL. Angew. Chem. Int. Ed. 2003; 42: 183
    • 7b Ma SM, Lu LH, Zhang JL. J. Am. Chem. Soc. 2004; 126: 9645
  • 8 Zhang DH, Du K, Shi M. Org. Biomol. Chem. 2012; 10: 3763
  • 9 Shan ZW, Peng M, Fan HX, Lu QT, Lu P, Zhao CS, Chen YL. Bioorg. Med. Chem. Lett. 2011; 21: 1731
    • 10a Lewis Acids in Organic Synthesis . Vol. 1, 2. Yamamoto H. Wiley-VCH; Weinheim: 2000
    • 10b Kobayashi S, Manabe K. Acc. Chem. Res. 2002; 35: 209
    • 10c Yamamoto Y. J. Org. Chem. 2007; 72: 7817
    • 10d Mandal SK, Roesky HW. Adv. Catal. 2011; 54: 1
  • 11 Feng Z, Min QQ, Xiao YL, Zhang B, Zhang XG. Angew. Chem. Int. Ed. 2014; 53: 1669
    • 12a Lewis Acids and Selectivity in Organic Synthesis . Pons JM, Santelli M. CRC Press; Boca Raton FL: 1996
    • 12b Leach MR. Lewis Acid/Base Reaction Chemistry . Metasynthesis.com; Brighton: 1999
    • 12c Dilman AD, Ioffe SL. Chem. Rev. 2003; 103: 733
    • 12d Corma A, Garcia H. Chem. Rev. 2003; 103: 4307
    • 12e Fu GC. J. Org. Chem. 2004; 69: 3245