Organic Letters
Letter
Chem. Rev. 2011, 111, 1170. (g) Liu, C.; Zhang, H.; Shi, W.; Lei, A. W.
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In summary, we have found an IL-promoter directed
annulation of 5-aryloxy-1H-pyrazole-4-carbaldehydes that
serves as a straightforward approach for chromeno[2,3-
c]pyrazol-4(1H)-ones formation via oxidative coupling of
aldehyde C−H bond and aromatic C−H bonds under metal-
free conditions in aqueous medium. In addition, the reaction
can tolerate diverse functional groups and can be applied to
obtain a rather wide range of products. Furthermore, promoter
IL5 can be easily recycled and reused with the same efficacies
for five cycles. In this sense, it is a useful complementary
method for synthesizing chromeno[2,3-c]pyrazol-4(1H)-ones.
ASSOCIATED CONTENT
* Supporting Information
■
S
Experimental procedure, NMR spectra, and analytical data for
all new compounds. This material is available free of charge via
(9) (a) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39,
3772. (b) Dupont, J.; Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002,
AUTHOR INFORMATION
Corresponding Author
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102, 3667. (c) Par
2615. (d) Xin, B. W.; Hao, J. C. Chem. Soc. Rev. 2014, 43, 7171.
(10) (a) Isambert, N.; Duque, M. M. S.; Plaquevent, J. C.; Genisson,
̂
vulescu, V. I.; Hardacre, C. Chem. Rev. 2007, 107,
Author Contributions
‡These authors contributed equally.
Notes
́
Y.; Rodriguez, J.; Constantieux, T. Chem. Soc. Rev. 2011, 40, 1347.
(b) Rizzo, C.; D’Anna, F.; Marullo, S.; Noto, R. J. Org. Chem. 2014, 79,
8678. (c) Martins, M. A. P.; Frizzo, C. P.; Tier, A. Z.; Moreira, D. N.;
Zanatta, N.; Bonacorso, H. G. Chem. Rev. 2014, 114, PR1.
(11) (a) Zhang, Q. H.; Zhang, S. G.; Deng, Y. Q. Green Chem. 2011,
13, 2619. (b) Taheri, A.; Liu, C. H.; Lai, B. B.; Cheng, C.; Pan, X. J.;
Gu, Y. L. Green Chem. 2014, 16, 3715.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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(12) (a) Holzer, W.; Ebner, A.; Schalle, K.; Batezila, G.; Eller, G. A. J.
Fluorine Chem. 2010, 131, 101. (b) Catarzi, D.; Cecchi, L.; Colotta, V.;
Filacchioni, G. J. Med. Chem. 1995, 38, 1330. (c) Sarenko, A. S.; Efros,
L. S.; Kvitko, I. Y. Pharm. Chem. J. 1970, 4, 23.
(13) For similar examples, see: (a) Rao, H. H.; Ma, X. Y.; Liu, Q. Z.;
Li, Z. F.; Cao, S. L.; Li, C. J. Adv. Synth. Catal. 2013, 355, 2191.
(b) Leifert, D.; Studer, A. Org. Lett. 2015, 17, 386.
We are grateful to NSFC (21162025 and 21262035), the
Program for Outstanding Youth Science and Technology
Innovation Talents Training in Xinjiang Uygur Autonomous
Region (2014721004), the Natural Science Foundation of
Xinjiang University (BS110133), and Key Laboratory of Oil &
Gas Fine Chemicals, Ministry of Education & Xinjiang Uyghur
Autonomous Region (XJDX0908-2013-1 and XJDX0908-2013-
2) for financial support of this research.
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