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
. 2019 Oct 17;9(57):33460-33464.
doi: 10.1039/c9ra06646b. eCollection 2019 Oct 15.

ZnBr2/Oxone-mediated ipso-cyclization of N-(3-phenylprop-2-yn-1-yl)aniline

Keke Huang  1 , Jia-Ni Li  2 , Guanyinsheng Qiu  2   3 , Wenlin Xie  4 , Jin-Biao Liu  1
Affiliations

ZnBr2/Oxone-mediated ipso-cyclization of N-(3-phenylprop-2-yn-1-yl)aniline

Keke Huang et al. RSC Adv. .

Abstract

In this work, a selective synthetic strategy towards 1-azaspiro[4.5]deca-3,6,9-trien-8-ones from N-tosyl-N-(prop-2-yn-1-yl)aniline is developed. The transformation proceeds smoothly in a mixed solvent including acetonitrile and water when ZnBr2 and Oxone are employed. Mechanism studies show that the reaction proceeds in a regioselective manner via a radical ipso-cyclization pathway.

PubMed Disclaimer

Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Proposed route for the synthesis of trienones.
Scheme 2
Scheme 2. Proposed mechanism.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

References

    1. For selected review, see:

    2. Peterson E. A. Overman L. E. Proc. Natl. Acad. Sci. U. S. A. 2004;101:11943. doi: 10.1073/pnas.0402416101. - DOI - PMC - PubMed

    1. For selected reviews on construction of quaternary carbon, see:

    2. Wang B. Tu Y.-Q. Acc. Chem. Res. 2011;44:1207. doi: 10.1021/ar200082p. - DOI - PubMed
    3. Song Z.-L. Fan C.-A. Tu Y.-Q. Chem. Rev. 2011;111:7523. doi: 10.1021/cr200055g. - DOI - PubMed
    4. Zhuo C.-X. Zheng C. You S.-L. Acc. Chem. Res. 2014;47:2558. doi: 10.1021/ar500167f. - DOI - PubMed
    5. Pouysegu L. Deffieux D. Quideau S. Tetrahedron. 2010;66:2235. doi: 10.1016/j.tet.2009.12.046. - DOI
    6. Sun W. Li G. Hong L. Wang R. Org. Biomol. Chem. 2016;14:2164. doi: 10.1039/C5OB02526E. - DOI - PubMed
    7. Ding Q. Zhou X. Fan R. Org. Biomol. Chem. 2014;12:4807. doi: 10.1039/C4OB00371C. - DOI - PubMed
    8. Duan Y. Jiang S. Han Y. Sun B. Zhang C. Chin. J. Org. Chem. 2016;36:1973. doi: 10.6023/cjoc201605007. - DOI

    1. For reviews, see:

    2. Song R. Xie Y. Chin. J. Chem. 2017;35:280. doi: 10.1002/cjoc.201600846. - DOI
    3. Shi L. Zhang W. Chen S. Lu L. Fan R. Tan J. Zheng C. Curr. Org. Chem. 2018;15:904.
    4. Vessally E. Babazadeh M. Didehban K. Hosseinian A. Edjlali L. Curr. Org. Chem. 2018;22:286. doi: 10.2174/1385272821666170914111817. - DOI
    5. Reddy C. R. Prajapti S. K. Warudikar K. Ranjan R. Rao B. B. Org. Biomol. Chem. 2017;15:3130. doi: 10.1039/C7OB00405B. - DOI - PubMed
    6. Liu G. Liu H. Qiu G. Pu S. Wu J. Chem. Commun. 2012;48:7049. doi: 10.1039/C2CC33375A. - DOI - PubMed
    7. Ni S. Zhou J. Mei H. Han J. Tetrahedron Lett. 2018;59:1309. doi: 10.1016/j.tetlet.2018.02.055. - DOI
    1. Zhang X. Larock R. C. J. Am. Chem. Soc. 2005;127:12230. doi: 10.1021/ja053079m. - DOI - PubMed
    1. Lanza T. Leardini R. Minozzi M. Nanni D. Spagnolo P. Zanardi G. Angew. Chem., Int. Ed. 2008;47:9439. doi: 10.1002/anie.200804333. - DOI - PubMed
    2. Zhou Y. Zhang X. Zhang Y. Ruan L. Zhang J. Zhang-Negrerie D. Du Y. Org. Lett. 2017;19:150. doi: 10.1021/acs.orglett.6b03455. - DOI - PubMed