SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 2: 669 - 676

DOI: https://doi.org/10.6023/cjoc202008023

Article

Ag-Catalyzed Reactions of 3-Trifluoroacetyl Indoles and Isocyano- acetates: An Efficient Process to (Z)-β-Trifluoromethylated Dehydrotryptophan Derivatives

  • Mingliang Zhang ,
  • Pin Zhao ,
  • Hao Yuan ,
  • An'an Zhang ,
  • Wenyu Zhang ,
  • Linlin Zheng ,
  • Dongqing Wu ,
  • Lantao Liu
Expand
  • 1 School of Chemistry and Chemical Engineering, Henan Engineering Laboratory of Green Synthesis for Pharmaceuticals, Shangqiu Normal University, Shangqiu, Henan 476000

Received date: 2020-08-13

  Revised date: 2020-09-06

  Online published: 2020-09-22

Supported by

the National Natural Science Foundation of China(21572126); the National Natural Science Foundation of China(21901152); the National Natural Science Foundation of China(U1904195); the Key Scientific and Technological Project of Henan Province(202102310003); the Key Scientific and Technological Project of Henan Province(192102210161); the Science and Technology Innovation Talents of Henan Province(2018JQ0011)

Fold

Abstract

Catalytic cyclization-rearrangement reaction of 3-trifluoroacetyl indole and isocyanoacetate was achieved with AgOAc as catalyst in mild conditions. A serious of β-trifluoromethylated dehydrotryptophan derivatives were obtained with single Z-isomer in excellent yields (up to >99% yields). The large scale experiment proceeded smothly genereting desired products in up to 98% isolated yield, which demostrated the practicality of the method. The plausible mechanism was aslo proposed. This transformation has features of high atom economy, mild reaction condition and easy operation.

Key words： 3-trifluoroacetyl indole; isocyanoacetate; dehydrotryptophan

Cite this article

Mingliang Zhang , Pin Zhao , Hao Yuan , An'an Zhang , Wenyu Zhang , Linlin Zheng , Dongqing Wu , Lantao Liu . Ag-Catalyzed Reactions of 3-Trifluoroacetyl Indoles and Isocyano- acetates: An Efficient Process to (Z)-β-Trifluoromethylated Dehydrotryptophan Derivatives[J]. Chinese Journal of Organic Chemistry, 2021 , 41(2) : 669 -676 . DOI: 10.6023/cjoc202008023

References

[1]
(a) Purser S.; Moore P.R.; Swallow S.; Gouverneur V. Chem. Soc. Rev. 2008, 37, 320.
[1]
(b) Wang J.; Sánchez-Roselló M.; Ace?a J.L.; del Pozo C.; Sorochinsky A.E.; Fustero S.; Soloshonok V.A.; Liu H. Chem. Rev. 2014, 114, 2432.
[1]
(c) Gillis E.P.; Eastman K.J.; Hill M.D.; Donnelly D.J.; Meanwell N.A. J. Med. Chem. 2015, 58, 8315.
[1]
(d) Zhou Y.; Wang J.; Gu Z.; Wang S.; Zhu W.; Acena J.L.; Soloshonok V.A.; Izawa K.; Liu H. Chem. Rev. 2016, 116, 422.
[2]
(a) Schlosser M. Angew. Chem., Int. Ed. 2006, 45, 5432.
[2]
(b) Hagmann W.K. J. Med. Chem. 2008, 51, 4359.
[2]
(c) Kirk K.L. Org. Process Res. Dev. 2008, 12, 305.
[2]
(d) Meanwell N.A. J. Med. Chem. 2011, 54, 2529.
[3]
For selected reviews, see: a Yang, X.; Wu, T.; Phipps, R. J.; Toste, F. D.Chem. Rev. 2015, 115, 826.
[3]
(b) Ma J.-A.; Cahard D. Chem. Rev. 2008, 108, PR1.
[3]
(c) Ma J.-A.; Cahard D. Chem. Rev. 2004, 104, 6119.
[3]
(d) Chu L.; Qing F.-L. Acc. Chem. Res. 2014, 47, 1513.
[4]
Hassinger H.L.; Soll R.M.; Gribble G.W. Tetrahedron Lett. 1998, 39, 3095.
[5]
Li J.; Li B.; Chen X.; Zhang G. Synlett 2003, 1447.
[6]
(a) Lanke V.; Bettadapur K.R.; Prabhu K.R. Org. Lett. 2016, 18, 5496.
[6]
(b) Lanke V.; Prabhu K.R. Chem. Commun. 2017, 53, 5117.
[6]
(c) Sherikar M.S.; Kapanaiah R.; Prabhu K.R. Chem. Commun. 2018, 54, 11200.
[6]
(d) Bettadapur K.R.; Kapanaiah R.; Lanke V.; Prabhu K.R. J. Org. Chem. 2018, 83, 1810.
[7]
(a) Marco R.D.; Cavina L.; Greco A.; Gentilucci L. Amino Acids 2014, 46, 2823.
[7]
Yeh E. Garneau S. Walsh C.T. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 3960.
[7]
(c) Bittner S.; Scherzer R.; Harlev E. Amino Acids 2007, 33, 19.
[7]
(d) Jiang J.; Ma Z.; Castle S.L. Tetrahedron 2015, 71, 5431.
[7]
(e) Lorena M.-T.; Albornoz-Grados, A.; Bertran, A.; Albericio, F.; Lavilla, R.Chem. Commun. 2017, 53, 2740.
[7]
(f) Kelley E.W.; Norman S.G.; Scheerer. J. R.Org. Biomol. Chem. 2017, 15, 8634.
[8]
(a) Olsen E.K.; Hansen E.; Moodie L. W. K.; Isaksson J.; Sep?i? K.; Cergolj M.; Svenson J.; Andersen J.H. Org. Biomol. Chem. 2016, 14, 1629.
[8]
(b) Lidgren G.; Bohlin L.; Bergman J. Tetrahedron Lett. 1986, 27, 3283.
[9]
Du F.-Y.; Li X.-M.; Li C.-S.; Shang Z.; Wang B.-G. Bioorg. Med. Chem. Lett. 2012, 22, 4650.
[10]
Block R.J. Chem. Rev. 1946, 38, 501.
[11]
Kimura R.; Nagano T.; Kinoshita H. Bull. Chem. Soc. Jpn. 2002, 75, 2517.
[12]
Kinoshita H.; Kometani M.; Ihara K.; Kimura R. Bull. Chem. Soc. Jpn. 2009, 82, 364.
[13]
(a) RajanBabu T.V.; Lim H.J.; Gallucci J.C. Org. Lett. 2010, 12, 2162.
[13]
(b) Feldman K.S.; Eastman K.J.; Lessene G. Org. Lett. 2002, 4, 3525.
[14]
Baran P.S.; Hafensteiner B.D.; Ambhaikar N.B.; Guerrero C. A.; Gallagher J.D. J. Am. Chem. Soc. 2006, 128, 8678.
[15]
(a) Merlic C.A.; Semmelhack M.F. J. Organomet. Chem. 1990, 391, C23.
[15]
(b) Harrington P.J.; Hegedus L. S.; Mcdaniel K.F. J. Am. Chem. Soc. 1987, 109, 4335.
[16]
(a) Yokoyama Y.; Takahashi M.; Takashima M.; Kohno Y.; Kobayashi H.; Kataoka K.; Shidori K.; Murakami Y. Chem. Pharm. Bull. 1994, 42, 832.
[16]
(b) Yokoyama Y.; Matsumoto T.; Murakami Y. J. Org. Chem. 1995, 60, 1486.
[17]
Kaur H.; Heapy A.M.; Brimble M.A. Org. Biomol. Chem. 2011, 9, 5897.
[18]
(a) Gulevich A.V.; Zhdanko A.G.; Orru R. V. A.; Nenajdenko V.G. Chem. Rev. 2010, 110, 5235.
[18]
(b) Elders N.; Ruijter E.; de Kanter F. J. J.; Groen M.B.; Orru R. V. A.Chem. Eur. J. 2008, 14, 4961.
[18]
(c) Enders D.; Chen Z.-X.; Raabe G. Synthesis 2005, 306.
Options
Outlines

/

〈 〉