Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2019; 51(21): 4048-4065
DOI: 10.1055/s-0039-1690155
DOI: 10.1055/s-0039-1690155
paper
Copper-Catalyzed 6-endo-dig O-Cyclization of 2-(But-3-en-1-yn-1-yl)benzamide
Rui-Xiang Wang∗
a
Department of chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, P. R. of China Email: liujinbiao@jxust.edu.cn
,
Zhuang Fang
a
Department of chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, P. R. of China Email: liujinbiao@jxust.edu.cn
,
b
College of Biological, Chemical Science and Engineering, Jiaxing University, 118 Jiahang Road, Jiaxing 314001, P. R. of China Email: qiuguanyinsheng@mail.zjxu.edu.cn
,
Wenlin Xie
c
School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Hunan 411201, P. R. of China
,
a
Department of chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, P. R. of China Email: liujinbiao@jxust.edu.cn
› Author AffiliationsFinancial support from the National Natural Science Foundation of China (51564021, 21762018 and 21772067), the Program of Qingjiang Excellent Young Talents, Jiangxi University of Science and Technology, and the Science and Technology Innovation Outstanding Young Talents Program of Jiangxi Province (20192BCBL23009) is gratefully acknowledged.Further Information
Publication History
Received: 21 June 2019
Accepted after revision: 23 July 2019
Publication Date:
14 August 2019 (online)
Abstract
The copper-catalyzed synthesis of 3-vinylisocoumarin-1-imine is reported. The transformation proceeds smoothly with good yields in THF and the regioselectivity was determined by a O-nucleophilic 6-endo cyclization. Studies on the mechanism indicate that copper trifluoroacetate serves as a Lewis acid, and the use of vinyl-connected 2-alkynylbenzamide is important for this O-nucleophilic 6-endo cyclization.
Key words
copper catalysis - O-nucleophilic 6-endo cyclization - Lewis acid - vinyl-connected 2-alkynylbenzamide - isocoumarinSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690156.
- Supporting Information
-
References
- 1a Boyarskiy VP, Ryabukhin DS, Bokach NA, Vasilyev AV. Chem. Rev. 2016; 116: 5894
- 1b Zheng Z, Wang Z, Wang Y, Zhang L. Chem. Soc. Rev. 2016; 45: 4448
- 1c Pirnot M, Wang Y.-M, Buchwald S. Angew. Chem. Int. Ed. 2016; 55: 48
- 1d Fuerstner A. Angew. Chem. Int. Ed. 2013; 52: 2794
- 1e Wu C, Wang Z, Hu Z, Zeng F, Zhang X.-Y, Cao Z, Tang Z, He W.-M, Xu X.-H. Org. Biomol. Chem. 2018; 16: 3177
- 1f Xie L.-Y, Peng S, Liu F, Yi J.-Y, Wang M, Tang Z, Xu X, He W.-M. Adv. Synth. Catal. 2018; 360: 4259
- 1g Wu C, Lu L.-H, Peng A.-Z, Jia G.-K, Peng C, Cao Z, Tang Z, He W.-M, Xu X. Green Chem. 2018; 20: 3683
- 1h Zheng Y, Liu M, Qiu G, Xie W, Wu J. Tetrahedron 2019; 75: 1663
- 1i Zong Y, Lang Y, Yang M, Li X, Fan X, Wu J. Org. Lett. 2019; 21: 1935
- 1j Gong X, Chen J, Li X, Xie W, Wu J. Chem. Asian J. 2018; 13: 2543
- 1k Zhao Y, Luo Y, Zhu Y, Wang H, Zhou H, Tan H, Zhou Z. Synlett 2018; 29: 773
- 1l Zhao Y.-H, Li Y, Luo M, Tang Z, Deng K. Synlett 2016; 27: 2597
- 1m Zhao Y, Li Y, Guo T, Tang Z, Xie W, Zhao G. Tetrahedron Lett. 2016; 57: 2257
- 1n Guo T, Liu Y, Zhao Y.-H, Zhang P.-K, Han S.-L, Liu H.-M. Tetrahedron Lett. 2016; 57: 4629
- 1o Guo T, Liu Y, Zhao Y.-H, Zhang P.-K, Han S.-L, Liu H.-M. Tetrahedron Lett. 2016; 57: 3920
- 1p Zhen L, Fang C, Zheng Y, Qiu G, Li X, Zhou H. Tetrahedron Lett. 2018; 59: 3934
- 1q Zhang L, Ma L, Zhou H, Yao J, Li X, Qiu G. Org. Lett. 2018; 20: 2407
- 2a Li DY, Shi KJ, Mao XF, Zhao ZL, Wu XY, Liu PN. Tetrahedron 2014; 70: 7022
- 2b Hu J, Wang X, Hu Y, Yang S, Liang Y. Green Sustainable Chem. 2011; 1: 165
- 2c Kanazawa C, Terada M. Asian J. Chem. 2009; 4: 1668
- 2d Brahmchari D, Akhilesh AK, Mehta S. J. Org. Chem. 2018; 83: 3339
- 2e Tan J, Tong Y, Chen Z. ChemistrySelect 2018; 3: 3886
- 2f Wu C, Wang J, Zhang X.-Y, Jia G.-K, Cao Z, Tang Z, Yu X, Xu X, He W.-M. Org. Biomol. Chem. 2018; 16: 5050
- 3a Neto JS. S, Back DF, Zeni G. Eur. J. Org. Chem. 2015; 1583
- 3b Mehta S, Yao T, Larock RC. J. Org. Chem. 2012; 77: 10938
- 3c Schlemmer C, Andernach L, Schollmeyer D, Straub BF, Opatz T. J. Org. Chem. 2012; 77: 10118
- 3d Mehta S, Waldo JP, Larock RC. J. Org. Chem. 2009; 74: 1141
- 3e Chinta BS, Sanapa H, Vasikarla KP, Baire B. Org. Biomol. Chem. 2018; 16: 3947
- 3f Oliver MA, Gandour RD. J. Org. Chem. 1984; 49: 558
- 4a Wang R.-X, Yuan S.-T, Liu J.-B, Wu J, Qiu G. Org. Biomol. Chem. 2018; 16: 4501
- 4b Wang Y.-H, Ouyang B, Qiu G, Zhou H, Liu J.-B. Org. Biomol. Chem. 2019; 17: 4335
- 4c Chen D, Shan Y, Li J, You J, Sun X, Qiu G. Org. Lett. 2019; 21: 4044
- 4d Wang Y.-C, Wang R.-X, Qiu G, Zhou H, Xie W, Liu J.-B. Org. Chem. Front. 2019; 6: 2471
- 5 Liu G, Ye D, Zhang D, Ding X, Jiang H, Liu H. Adv. Synth. Catal. 2009; 351: 2605
- 6a Madich Y, Alvarez R, Aurrecoechea JM. Eur. J. Org. Chem. 2015; 6298
- 6b Bian M, Yao W, Ding H, Ma C. J. Org. Chem. 2010; 75: 269
- 6c Bianchi G, Chiarini M, Marinelli F, Rossi L, Arcadi A. Adv. Synth. Catal. 2010; 352: 136
- 6d Alvarez R, Martinez C, Madich Y, Denis JG, Aurrecoechea JM, de Lera AR. Eur. J. Chem. 2010; 16: 12746
- 6e Ding D, Mou T, Xue J, Jiang X. Chem. Commun. 2017; 53: 5279
- 6f Fu X, Meng Y, Li X, Stepien M, Chemielewski PJ. Chem. Commun. 2018; 54: 2510
- 6g Li X, Liu B, Chmielewski PJ, Xu X. J. Org. Chem. 2012; 77: 8206
- 6h Doherty S, Knight JG, Perry DO, Ward NA. B, Bittner DM, McFarlane W, Wills C, Probert MR. Organometallics 2016; 35: 1265
- 6i Minami H, Sueda T, Okamoto N, Miwa Y, Ishikura M, Yanada R. Eur. J. Org. Chem. 2016; 541
- 7a Zhang X, Yang C, Zhang-Negrerie D, Du Y. Chem. Eur. J. 2015; 21: 5192
- 7b Ha Tu M, Yao B, Wang Q, Zhu J. Org. Lett. 2015; 7: 1750
- 7c Dev K, Maurya R. RSC Adv. 2015; 5: 13102
- 7d Dong J, Wang F, You J. Org. Lett. 2014; 16: 2884
- 7e Yao B, Wang Q, Zhu J. Angew. Chem. Int. Ed. 2012; 51: 5170
- 7f Luo Y, Wu J. Chem. Commun. 2011; 47: 11137
- 7g Ding D, Zhu G, Jiang X. Angew. Chem. Int. Ed. 2018; 57: 9028
- 7h Madich Y, Alvarez R, Aurrecoechea JM. Eur. J. Org. Chem. 2014; 6263
- 7i Jithunsa M, Ueda M, Miyata O. Org. Lett. 2011; 13: 518
- 7j Mancuso R, Ziccarelli I, Armentano D, Marino N, Giofre SV, Gabriele B. J. Org. Chem. 2014; 79: 3506
- 7k Yao B, Jaccoud C, Wang Q, Zhu J. Eur. J. Chem. 2012; 18: 5864
- 7l Yan Z.-Y, Tan C.-M, Wang X, Li F, Cao G.-L, Chen X.-M, Wu W.-S, Wang J.-J. Synlett 2011; 1863
- 7m Bantreil X, Bourderioux A, Mateo P, Hagerman CE, Selkti M, Brachet E, Belmont P. Org. Lett. 2016; 18: 481
- 7n Qiu S, Wang C, Xie S, Huang X, Chen L, Zhao Y, Zeng Z. Chem. Commun. 2018; 54: 11383
- 7o Guo T, Jiang J.-J, Yang S, Chen H, Fu Y.-N, Han S.-L, Zhao Y.-H. Org. Biomol. Chem. 2018; 16: 6039
- 7p Wang Y.-H, Qiu G, Zhou H, Xie W, Liu J.-B. Tetrahedron 2019; 75: 3850
- 7q Yang M, Hu X, Ouyang B, Xie W, Liu J.-B. Tetrahedron 2019; 75: 3516
- 8a Zhou K, Zhang J, Qiu G, Wu J. Org. Lett. 2019; 21: 275
- 8b Ouyang B, Liu D, Xia K, Qiu G. Synlett 2018; 29: 111
- 8c Qiu G, Wu J. Chem. Commun. 2012; 48: 6046
- 8d Liu J.-B, Chen F.-J, Liu E, Qiu G. New J. Chem. 2015; 39: 7773
- 9a Larsen TO, Breinholt J. J. Nat. Prod. 1999; 62: 1182
- 9b Wang B, Li M, Xu S, Song H, Wang B. Synthesis 2007; 1643
- 9c Alper PB, Nguyen KT. J. Org. Chem. 2003; 68: 2051
- 9d Hudson AR, Roach SL, Higuchi RI, Phillips DP, Bissonnette RP, Lamph WW, Yen J, Li Y, Adams ME, Valdez LJ, Vassar A, Cuervo C, Kallel EA, Gharbaoui CJ, Mais DE, Miner JN, Marschke KB, Rungta D, Negro-Vilar A, Zhi L. J. Med. Chem. 2007; 50: 4699
- 9e Xie W, Zhang H, He J, Zhang J, Yu Q, Luo C, Li S. Bioorg. Med. Chem. Lett. 2017; 27: 530
- 9f Xie W, Xie S, Zhou Y, Tang X, Liu J, Yang W, Qiu M. Eur. J. Med. Chem. 2014; 81: 22
- 9g Ma C, Zhou J.-Y, Zhang Y.-Z, Jiao Y, Mei G.-L, Shi F. Chem. Asian J. 2018; 13: 2549
- 9h Xie W, Wu Y, Zhang J, Mei Q, Zhang Y, Zhu N, Liu R, Zhang H. Eur. J. Med. Chem. 2018; 145: 35
- 10a Gong X, Wang M, Ye S, Wu J. Org. Lett. 2019; 21: 1156
- 10b Ye S, Qiu G, Wu J. Chem. Commun. 2019; 55: 1013
- 10c Ye S, Zheng D, Wu J, Qiu G. Chem. Commun. 2019; 55: 2214
- 10d Ye S, Li Y, Wu J, Li Z. Chem. Commun. 2019; 55: 2489
- 10e Gong X, Li X, Xie W, Wu J, Ye S. Org. Chem. Front. 2019; 6: 1863
- 10f Zhang J, Xie W, Ye S, Wu J. Org. Chem. Front. 2019; 6: 2254
- 10g Ye S, Xiang T, Li X, Wu J. Org. Chem. Front. 2019; 6: 2183
- 10h Ye S, Li X, Xie W, Wu J. Asian J. Org. Chem. 2019; 8: 893
- 10i Wang X, Yang M, Xie W, Fan X, Wu J. Chem. Commun. 2019; 55: 6010
- 11 CCDC 1941980 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
For selected reviews on dual-functionalized synthons, see:
For examples, see:
For 5-exo-dig N-attacked cyclization of o-alkynylbenzamide, see:
For selected examples of electrophilic cyclization, see:
For 6-endo-dig O-attacked cyclization of 2-alkynylbenzamide, see:
For transition-metal-catalyzed 5-exo-dig O-cyclization of 2-alkynylbenzamide, see:
For selected examples on cyclization under copper catalysis, see: