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

doi:10.6023/cjoc202008023

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 669-676.DOI: 10.6023/cjoc202008023 Previous Articles Next Articles

Article

银催化的3-三氟乙酰基吲哚与异氰酸酯反应: (Z)-β-三氟甲基取代的脱氢色氨酸衍生物的高效合成

张明亮¹, 赵聘¹, 袁浩¹, 张安安¹, 张文宇¹, 郑琳琳¹, 吴冬青¹^,^*(), 刘澜涛¹^,^*()

1 商丘师范学院化学化工学院药物绿色合成河南省工程实验室河南商丘 476000

收稿日期:2020-08-13 修回日期:2020-09-06 发布日期:2020-09-22
通讯作者: 吴冬青, 刘澜涛
作者简介:
* Corresponding authors. E-mail: liult05@iccas.ac.cn; iamwudongqing@163.com
基金资助:
国家自然科学基金(21572126); 国家自然科学基金(21901152); 国家自然科学基金(U1904195); 河南省科技攻关(202102310003); 河南省科技攻关(192102210161); 河南省科技创新杰出人才(2018JQ0011)

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

Mingliang Zhang¹, Pin Zhao¹, Hao Yuan¹, An'an Zhang¹, Wenyu Zhang¹, Linlin Zheng¹, Dongqing Wu¹^,^*(), Lantao Liu¹^,^*()

1 School of Chemistry and Chemical Engineering, Henan Engineering Laboratory of Green Synthesis for Pharmaceuticals, Shangqiu Normal University, Shangqiu, Henan 476000

Received:2020-08-13 Revised:2020-09-06 Published:2020-09-22
Contact: Dongqing Wu, Lantao Liu
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)

1. cjoc202008023.pdf(4659KB)

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

References 18

[1]	(a) Purser S.; Moore P.R.; Swallow S.; Gouverneur V. Chem. Soc. Rev. 2008, 37, 320. doi: 10.1039/B610213C
	(b) Wang J.; Sánchez-Roselló M.; Aceña J.L.; del Pozo C.; Sorochinsky A.E.; Fustero S.; Soloshonok V.A.; Liu H. Chem. Rev. 2014, 114, 2432. doi: 10.1021/cr4002879
	(c) Gillis E.P.; Eastman K.J.; Hill M.D.; Donnelly D.J.; Meanwell N.A. J. Med. Chem. 2015, 58, 8315. doi: 10.1021/acs.jmedchem.5b00258
	(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. doi: 10.1021/acs.chemrev.5b00392
[2]	(a) Schlosser M. Angew. Chem., Int. Ed. 2006, 45, 5432. doi: 10.1002/(ISSN)1521-3773
	(b) Hagmann W.K. J. Med. Chem. 2008, 51, 4359. doi: 10.1021/jm800219f
	(c) Kirk K.L. Org. Process Res. Dev. 2008, 12, 305. doi: 10.1021/op700134j
	(d) Meanwell N.A. J. Med. Chem. 2011, 54, 2529. doi: 10.1021/jm1013693
[3]	For selected reviews, see: a Yang, X.; Wu, T.; Phipps, R. J.; Toste, F. D.Chem. Rev. 2015, 115, 826. doi: 10.1021/cr500277b
	(b) Ma J.-A.; Cahard D. Chem. Rev. 2008, 108, PR1. doi: 10.1021/cr800221v
	(c) Ma J.-A.; Cahard D. Chem. Rev. 2004, 104, 6119. doi: 10.1021/cr030143e
	(d) Chu L.; Qing F.-L. Acc. Chem. Res. 2014, 47, 1513. doi: 10.1021/ar4003202
[4]	Hassinger H.L.; Soll R.M.; Gribble G.W. Tetrahedron Lett. 1998, 39, 3095. doi: 10.1016/S0040-4039(98)00505-X
[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. doi: 10.1021/acs.orglett.6b02698
	(b) Lanke V.; Prabhu K.R. Chem. Commun. 2017, 53, 5117. doi: 10.1039/C7CC00763A
	(c) Sherikar M.S.; Kapanaiah R.; Prabhu K.R. Chem. Commun. 2018, 54, 11200. doi: 10.1039/C8CC06264A
	(d) Bettadapur K.R.; Kapanaiah R.; Lanke V.; Prabhu K.R. J. Org. Chem. 2018, 83, 1810. doi: 10.1021/acs.joc.7b02719
[7]	(a) Marco R.D.; Cavina L.; Greco A.; Gentilucci L. Amino Acids 2014, 46, 2823. doi: 10.1007/s00726-014-1839-3 pmid: 17031473
	Yeh E. Garneau S. Walsh C.T. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 3960. pmid: 17031473
	(c) Bittner S.; Scherzer R.; Harlev E. Amino Acids 2007, 33, 19. pmid: 17031473
	(d) Jiang J.; Ma Z.; Castle S.L. Tetrahedron 2015, 71, 5431. doi: 10.1016/j.tet.2015.06.001 pmid: 17031473
	(e) Lorena M.-T.; Albornoz-Grados, A.; Bertran, A.; Albericio, F.; Lavilla, R.Chem. Commun. 2017, 53, 2740. doi: 10.1039/C7CC00555E pmid: 17031473
	(f) Kelley E.W.; Norman S.G.; Scheerer. J. R.Org. Biomol. Chem. 2017, 15, 8634. doi: 10.1039/C7OB02297B pmid: 17031473
[8]	(a) Olsen E.K.; Hansen E.; Moodie L. W. K.; Isaksson J.; Sepčić K.; Cergolj M.; Svenson J.; Andersen J.H. Org. Biomol. Chem. 2016, 14, 1629. doi: 10.1039/C5OB02416A
	(b) Lidgren G.; Bohlin L.; Bergman J. Tetrahedron Lett. 1986, 27, 3283. doi: 10.1016/S0040-4039(00)84776-0
[9]	Du F.-Y.; Li X.-M.; Li C.-S.; Shang Z.; Wang B.-G. Bioorg. Med. Chem. Lett. 2012, 22, 4650. doi: 10.1016/j.bmcl.2012.05.088
[10]	Block R.J. Chem. Rev. 1946, 38, 501. doi: 10.1021/cr60121a004
[11]	Kimura R.; Nagano T.; Kinoshita H. Bull. Chem. Soc. Jpn. 2002, 75, 2517. doi: 10.1246/bcsj.75.2517
[12]	Kinoshita H.; Kometani M.; Ihara K.; Kimura R. Bull. Chem. Soc. Jpn. 2009, 82, 364. doi: 10.1246/bcsj.82.364
[13]	(a) RajanBabu T.V.; Lim H.J.; Gallucci J.C. Org. Lett. 2010, 12, 2162. doi: 10.1021/ol100663y pmid: 12323060
	(b) Feldman K.S.; Eastman K.J.; Lessene G. Org. Lett. 2002, 4, 3525. pmid: 12323060
[14]	Baran P.S.; Hafensteiner B.D.; Ambhaikar N.B.; Guerrero C. A.; Gallagher J.D. J. Am. Chem. Soc. 2006, 128, 8678. pmid: 16802835
[15]	(a) Merlic C.A.; Semmelhack M.F. J. Organomet. Chem. 1990, 391, C23. doi: 10.1016/0022-328X(90)80183-Z
	(b) Harrington P.J.; Hegedus L. S.; Mcdaniel K.F. J. Am. Chem. Soc. 1987, 109, 4335. doi: 10.1021/ja00248a032
[16]	(a) Yokoyama Y.; Takahashi M.; Takashima M.; Kohno Y.; Kobayashi H.; Kataoka K.; Shidori K.; Murakami Y. Chem. Pharm. Bull. 1994, 42, 832. doi: 10.1248/cpb.42.832
	(b) Yokoyama Y.; Matsumoto T.; Murakami Y. J. Org. Chem. 1995, 60, 1486. doi: 10.1021/jo00111a004
[17]	Kaur H.; Heapy A.M.; Brimble M.A. Org. Biomol. Chem. 2011, 9, 5897. doi: 10.1039/c1ob05777d
[18]	(a) Gulevich A.V.; Zhdanko A.G.; Orru R. V. A.; Nenajdenko V.G. Chem. Rev. 2010, 110, 5235. doi: 10.1021/cr900411f
	(b) Elders N.; Ruijter E.; de Kanter F. J. J.; Groen M.B.; Orru R. V. A.Chem. Eur. J. 2008, 14, 4961. doi: 10.1002/(ISSN)1521-3765
	(c) Enders D.; Chen Z.-X.; Raabe G. Synthesis 2005, 306.

银催化的3-三氟乙酰基吲哚与异氰酸酯反应: (Z)-β-三氟甲基取代的脱氢色氨酸衍生物的高效合成

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

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 6

References 18

Related Articles 1

Recommended Articles

Metrics

Comments

Entry	Cat.	Solvent	T/℃	Time/h	Yield^b/%
1	Ag₂O	DCM	35	48	70
2	Ag₂CO₃	DCM	35	48	76
3	AgOAc	DCM	35	48	87
4	AgNO₃	DCM	35	48	N.R.
5	AgOAc	CHCl₃	35	48	71
6	AgOAc	Toluene	35	48	60
7	AgOAc	CH₃CN	35	48	60
8	AgOAc	MTBE	35	48	84
9	AgOAc	THF	35	48	88
10	AgOAc	1,4-Dioxane	35	24	>99
11	AgOAc	1,4-Dioxane	25	48	90
12	AgOAc	1,4-Dioxane	40	24	92
13 ^c	AgOAc	1,4-Dioxane	35	48	80
14 ^d	AgOAc	1,4-Dioxane	35	48	60
15 ^e	AgOAc	1,4-Dioxane	35	24	82
16 ^f	AgOAc	1,4-Dioxane	35	60	53