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
. 2018 Jan 25;8(9):4584-4587.
doi: 10.1039/c7ra12716b. eCollection 2018 Jan 24.

Catalyst- and solvent-free approach to 2-arylated quinolines via [5 + 1] annulation of 2-methylquinolines with diynones

Hai-Yuan Zhao  1   2 , Fu-Song Wu  2 , Li Yang  3 , Ying Liang  1 , Xiao-Lin Cao  2 , Heng-Shan Wang  2 , Ying-Ming Pan  2
Affiliations

Catalyst- and solvent-free approach to 2-arylated quinolines via [5 + 1] annulation of 2-methylquinolines with diynones

Hai-Yuan Zhao et al. RSC Adv. .

Abstract

A novel route for the synthesis of 2-arylated quinolines through a [5 + 1] annulation directly from 2-methylquinolines and diynones under catalyst-free and solvent-free conditions was disclosed. This synthetic process was atom-economic, with good tolerance of a broad range of functional groups, and with great practical worth.

PubMed Disclaimer

Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. C–H bond activation of 2-methylquinolines and 2-methylpyridine.
Fig. 1
Fig. 1. X-ray crystal structure of 3a (CCDC 1534893†).
Scheme 2
Scheme 2. Control experiments.
Scheme 3
Scheme 3. Plausible mechanism.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

References

    1. Hitora Y. Takada K. Ise Y. Okada S. Matsunaga S. J. Nat. Prod. 2016;79:2973. doi: 10.1021/acs.jnatprod.6b00710. - DOI - PubMed
    2. Fan H. Peng J.-G. Hamann M. T. Hu J.-F. Chem. Rev. 2008;108:264. doi: 10.1021/cr078199m. - DOI - PMC - PubMed
    3. Boucherle B. Haudecoeur R. Queiroz E. F. de Waard M. Wolfender J.-L. Robins R. J. Boumendjel A. Nat. Prod. Rep. 2016;33:1034. doi: 10.1039/C6NP00039H. - DOI - PubMed
    4. Tang H.-T. Xiong K. Li R.-H. Ding Z.-C. Zhan Z.-P. Org. Lett. 2015;17:326. doi: 10.1021/ol503437n. - DOI - PubMed
    5. Wen J.-J. Tang H.-T. Xiong K. Ding Z.-C. Zhan Z.-P. Org. Lett. 2014;16:5940. doi: 10.1021/ol502968c. - DOI - PubMed
    6. Tang X. Zhu Z. Qi C. Wu W. Jiang H. Org. Lett. 2016;18:180. doi: 10.1021/acs.orglett.5b03188. - DOI - PubMed
    7. Li P. Zhang X. Fan X. J. Org. Chem. 2015;80:7508. doi: 10.1021/acs.joc.5b01092. - DOI - PubMed
    8. Zhang S.-S. Wu J.-Q. Liu X. Wang H. ACS Catal. 2015;5:210. doi: 10.1021/cs501601c. - DOI
    1. Gutekunst W. R. Gianatassio R. Baran P. S. Angew. Chem., Int. Ed. 2012;124:7625. doi: 10.1002/ange.201203897. - DOI - PMC - PubMed
    2. Arockiam P. B. Bruneau C. Dixneuf P. H. Chem. Rev. 2012;112:5879. doi: 10.1021/cr300153j. - DOI - PubMed
    3. Cho S. H. Kim J. Y. Kwak J. Chang S. Chem. Soc. Rev. 2011;40:5068. doi: 10.1039/C1CS15082K. - DOI - PubMed
    4. Chen X. Engle K. M. Wang D.-H. Yu J.-Q. Angew. Chem., Int. Ed. 2009;121:5196. doi: 10.1002/ange.200806273. - DOI - PubMed
    1. Friesen R. W. Brideau C. Chan C. C. Charleson S. Deschênes D. Dubé D. Ethier D. Fortin R. Gauthier J. Y. Girard Y. Gordon R. Greig G. M. Riendeau D. Savoie C. Wang Z. Wong E. Visco D. Xu L. J. Young R. N. Bioorganic Med. Chem. Lett. 1998;8:2777. doi: 10.1016/S0960-894X(98)00499-5. - DOI - PubMed
    1. Quirk J. Thornton M. Kirkpatrick P. Nature. 2003;2:769. - PubMed
    1. Capdeville R. Buchdunger E. Zimmermann J. Matter A. Nature. 2002;1:493. - PubMed