Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2010 May 21;12(10):2234-7.
doi: 10.1021/ol100586r.

Synthesis of 2H-indazoles by the [3 + 2] cycloaddition of arynes and sydnones

Affiliations

Synthesis of 2H-indazoles by the [3 + 2] cycloaddition of arynes and sydnones

Chunrui Wu et al. Org Lett. .

Abstract

A rapid and efficient synthesis of 2H-indazoles has been developed, which involves the [3 + 2] dipolar cycloaddition of arynes and sydnones. The process proceeds under mild reaction conditions in good to excellent yields.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Proposed Cycloaddition of Sydnones and Arynes

References

    1. For excellent reviews of indazole’s activity and synthesis, see: Cerecetto H, Gerpe A, González M, Arán VJ, de Ocáriz CO. Mini-Rev. Med. Chem. 2005;5:869. Stadlbauer W. Science of Synthesis. Vol. 12. Stuttgart: Georg Thieme; 2002. pp. 227–324.

    1. Andreonati S, Sava V, Makan S, Kolodeev G. Pharmazie. 1999;54:99. - PubMed
    2. Paluchowska MH, Duszynska B, Klodzinska A, Tatarzynska E. Pol. J. Pharmacol. 2000;52:209. - PubMed
    1. Saczewski F, Saczewski J, Hudson AL, Tyacke RJ, Nutt DJ, Man J, Tabin P. Eur. J. Pharmaceutical Sci. 2003;20:201. - PubMed
    1. López-Alvarado P, Avendaño C, Menéndez JC. J. Org. Chem. 1995;60:5678. Lam PYS, Clark CG, Saubern S, Adams J, Winters MP, Chan DMT, Combs A. Tetrahedron Lett. 1998;39:2941. Fedorov AY, Finet J-P. Tetrahedron Lett. 1999;40:2747. Claramunt RM, Elguero J, Garceran R. Heterocycles. 1985;23:2895. (e) For one successful example, see: Slade DJ, Pelz NF, Bodnar W, Lampe JW, Watson PS. J. Org. Chem. 2009;74:6331.

    1. Halland N, Nazaré M, R’kyek O, Alonso J, Urmann M, Lindenschmidt A. Angew. Chem., Int. Ed. 2009;48:6879. - PubMed
    2. Song JJ, Yee NK. Org. Lett. 2000;2:519. - PubMed
    3. Haag B, Peng Z, Knochel P. Org. Lett. 2009;11:4270. - PubMed
    4. Taher A, Ladwa S, Rajan ST, Weaver GW. Tetrahedron Lett. 2000;41:9893.
    5. Varughese DJ, Manhas MS, Bose AK. Tetrahedron Lett. 2006;47:6795.
    6. Lee KY, Gowrisankar S, Kim JN. Tetrahedron Lett. 2005;46:5387.

Publication types