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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 12: 4227 - 4238

DOI: https://doi.org/10.6023/cjoc202304003

ARTICLES

Tin Powder-Promoted Synthesis of 1,3-Disubstituted 1,3-Dihydroisobenzofuran Compounds

  • Duoduo Tang ,
  • Danfeng Huang ,
  • Kehu Wang ,
  • Hu Ma ,
  • Yang Feng ,
  • Yuanyuan Ren ,
  • Junjiao Wang ,
  • Yulai Hu
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  • College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070
*

Received date: 2023-04-04

  Revised date: 2023-06-05

  Online published: 2023-08-15

Supported by

National Natural Science Foundation of China(21861033); National Natural Science Foundation of China(22061037)

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Abstract

An efficient approach for the construction of 1,3-disubstituted-1,3-dihydroisobenzofuran compounds was developed through tin powder mediated tandem allylation/oxa-Michael addition reaction of o-formyl chalcones with various allyl bromides under mild reaction conditions. This method is easy to operate and can tolerate various functional groups to give the corresponding 1,3-disubstituted-1,3-dihydroisobenzofuran compounds in good to excellent yields.

Key words： tin powder; allyl bromide; o-formyl chalcone; 1,3-dihydroisobenzofuran

Cite this article

Duoduo Tang , Danfeng Huang , Kehu Wang , Hu Ma , Yang Feng , Yuanyuan Ren , Junjiao Wang , Yulai Hu . Tin Powder-Promoted Synthesis of 1,3-Disubstituted 1,3-Dihydroisobenzofuran Compounds[J]. Chinese Journal of Organic Chemistry, 2023 , 43(12) : 4227 -4238 . DOI: 10.6023/cjoc202304003

References

[1]
Karmakar R.; Pahari P.; Mal D. Chem. Rev. 2014, 114, 6213.
[2]
Lovey R. G.; Elliott A. J.; Kaminski J. J.; Loebenberg D.; Parme- giani R. M.; Rane D. F.; Girijavallabhan V. M.; Pike R. E.; Guzik H.; Antonacci B. J. Med. Chem. 1992, 35, 4221.
[3]
Len C.; Selouane A.; Postel D.; Villa P.; Aubertin A.-M.; Egron D.; Gosselin G.; Périgaud C. Nucleos. Nucleot. Nucl. 2003, 22, 943.
[4]
Coote S. J.; Davies S. G.; Middlemiss D.; Naylor A. J. Organomet. Chem. 1989, 379, 81.
[5]
Luzzio F. A.; Okoromoba O. E. Tetrahedron Lett. 2011, 52, 6530.
[6]
Yuan H.; Gong Y. J. Fluorine Chem. 2013, 149, 125.
[7]
Wei X.; Chen G.; Peng Y. Tetrahedron Lett. 2020, 61, 152174.
[8]
Maity S.; Saha M.; Hazra G.; Ghorai P. Org. Lett. 2017, 19, 5872.
[9]
Nath U.; Chowdhury D.; Pan S. C. Adv. Synth. Catal. 2018, 360, 1628.
[10]
Yang X.; Pang S.; Cheng F.; Zhang Y.; Lin Y.-W.; Yuan Q.; Zhang F.-L.; Huang Y.-Y. J. Org. Chem. 2017, 82, 10388.
[11]
Bao M.; Nakamura H.; Inoue A.; Yamamoto Y. Chem. Lett. 2002, 31, 158.
[12]
Capriati V.; Florio S.; Luisi R.; Perna F. M.; Salomone A. J. Org. Chem. 2006, 71, 3984.
[13]
Chao B.; Dittmer D. C. Tetrahedron Lett. 2000, 41, 6001.
[14]
Jarrige L.; Carboni A.; Dagousset G.; Levitre G.; Magnier E.; Masson G. Org. Lett. 2016, 18, 2906.
[15]
Mukaiyama T.; Harada T. Chem. Lett. 1981, 10, 1527.
[16]
(a) Zhao P.; Huang D.; Wang F.; Han T.; Yang M.; Wang K. H.; Hu Y. Appl. Organomet. Chem. 2021, 36, e6479.
[16]
(b) Wang S.; Wang K. H.; Chang B.; Huang D.; Hu Y. Appl. Organomet. Chem. 2021, 35, e6249.
[16]
(c) Wang X.; Huang D.; Wang K. H.; Liu J.; Zong W.; Wang J.; Su Y.; Hu Y. Appl. Organomet. Chem. 2019, 33, e4995.
[16]
(d) Wang X.; Huang D.; Wang K. H.; Su Y.; Hu Y. J. Org. Chem. 2019, 84, 6946.
[16]
(e) Elaas N. A.; Elaas W. A.; Huang D.; Hu Y.; Wang K.-H. Curr. Org. Synth. 2017, 14, 1156.
[17]
Zhao Z.; Wang J.; Huang D.; Yang Z.; Zhao F.; Hu Y.; Xu W.; Hu Y. Chin. J. Org.Chem. 2020, 40, 2026. (in Chinese)
[17]
(赵转霞, 王君姣, 黄丹凤, 杨政, 赵芳霞, 虎永琴, 徐炜刚, 胡雨来, 有机化学, 2020, 40, 2026.)
[18]
(a) Yamamoto Y.; Asao N. Chem. Rev. 1993, 93, 2207.
[18]
(b) Zha Z.; Qiao S.; Jiang J.; Wang Y.; Miao Q.; Wang Z. Tetrahedron 2005, 61, 2521.
[19]
Marshall J. A. Chem. Rev. 1996, 96, 31.
[20]
Roy U. K.; Roy S. Chem. Rev. 2010, 110, 2472.
[21]
Shen Z.-L.; Wang S.-Y.; Chok Y.-K.; Xu Y.-H.; Loh T.-P. Chem. Rev. 2013, 113, 271.
[22]
Tan K.-T.; Chng S.-S.; Cheng H.-S.; Loh T.-P. J. Am. Chem. Soc. 2003, 125, 2958.
[23]
Zhang J.; Blazecka P. G.; Berven H.; Belmont D. Tetrahedron Lett. 2003, 44, 5579.
[24]
Wang Z.; Zha Z.; Zhou C. Org. Lett. 2002, 4, 1683.
[25]
Zha Z.; Xie Z.; Zhou C.; Chang M.; Wang Z. New J. Chem. 2003, 27, 1297.
[26]
(a) Ravindra B.; Das B. G.; Ghorai P. Org. Lett. 2014, 16, 5580.
[26]
(b) Kumar P.; Shirke R. P.; Yadav S.; Ramasastry S. S. V. Org. Lett. 2021, 23, 4909.
[27]
Tripathi C. B.; Mukherjee S. Angew. Chem., Int. Ed. 2013, 52, 8450.
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