Transition-Metal-Free Direct Arylation and Esterification Reaction of Unprotected Indolylcarboxylic Acid Derivatives: A New Entry to 2-(1H-Indol-2-yl)-5-(phenylthio)-1,3,4-oxadiazoles and Aryl 1H-Indole-2-carboxylates

Dawei Wang; Chenyang Ge; Xin Yu; Huida Wan; Xiang Xu

doi:10.1055/s-0035-1562526

Synlett, Inhaltsverzeichnis

Synlett 2016; 27(18): 2616-2620
DOI: 10.1055/s-0035-1562526

letter

Transition-Metal-Free Direct Arylation and Esterification Reaction of Unprotected Indolylcarboxylic Acid Derivatives: A New Entry to 2-(1H-Indol-2-yl)-5-(phenylthio)-1,3,4-oxadiazoles and Aryl 1H-Indole-2-carboxylates

Dawei Wang*

^aThe Key Laboratory of Food Colloids and Biotechnology, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, Jiangsu Province, P. R. of China eMail: wangdw@jiangnan.edu.cn

,

Chenyang Ge

^aThe Key Laboratory of Food Colloids and Biotechnology, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, Jiangsu Province, P. R. of China eMail: wangdw@jiangnan.edu.cn

,

Xin Yu

^aThe Key Laboratory of Food Colloids and Biotechnology, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, Jiangsu Province, P. R. of China eMail: wangdw@jiangnan.edu.cn

,

Huida Wan

^aThe Key Laboratory of Food Colloids and Biotechnology, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, Jiangsu Province, P. R. of China eMail: wangdw@jiangnan.edu.cn

,

Xiang Xu*

^bCollege of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, P. R. of China eMail: rainerxu@163.com

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

An efficient, ligand-free, transition-metal-free, direct arylation and esterification reaction of unprotected indolylcarboxylic acid derivatives with diaryliodonium salts was developed, thus providing a new entry to 2-(1H-indol-2-yl)-5-(phenylthio)-1,3,4-oxadiazole and aryl 1H-indole-2-carboxylate derivatives with good yields.

Keywords

arylation - diaryliodonium salts - indolylcarboxylic acids - esterification - transition-metal-free

Volltext

Referenzen

References and Notes

1a Olgen S, Nebioglu D. Farmaco 2002; 57: 677
1b Oelgen S, Coban T. Biol. Pharm. Bull. 2003; 26: 736
1c Heindl J, Albrecht R, Loge O, Lehmann M, Kelm HW. DE 3207241, 1983
1d Heindl J, Loge O. EP 62919, 1982
1e Nadzan AM, Lin CW, Kerwin JF. PE 308885, 1989
1f Flouret G, Arnold ZS, Majewski T, Petousis NH, Mahan K, Farooqui F, Blum KA, Konopinska D, Natarajan S, Crich D. J. Pept. Sci. 1995; 1: 89
1g Mochizuki A, Nakamoto Y, Naito H, Uoto K, Ohta T. Bioorg. Med. Chem. Lett. 2008; 18: 782
1h Ohta T, Komoriya S, Yoshino T, Uoto K, Nakamoto Y, Naito H, Mochizuki A, Nagata T, Kanno H, Haginoya N. US 20050020645, 2005
1i Ohta T, Komoriya S, Yoshino T, Uoto K, Nakamoto Y, Naito H, Mochizuki A, Nagata T, Kanno H, Haginoya N. WO 2003000680, 2003
1j Bao Y.-S, Baiyin M, Bao A, Jia M, Bao Z. J. Org. Chem. 2014; 79: 6715
1k Bao Y.-S, Bao Z, Bao A, Baiyin M, Jia M. J. Org. Chem. 2014; 79: 803
1l Narayana B, Ashalatha BV, Raj KK. V, Sarojini BK. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2009; 48: 1794
1m Kaushik D, Khan SA, Chawla G. Eur. J. Med. Chem. 2010; 45: 3960

2 Oelgen S, Coban T. Biol. Pharm. Bull. 2003; 26: 736
3 Takemura M, Ota T, Uoto K, Kawakami K, Yoshino T, Yokomizo Y, Oshikawa K. JP 2004203791, 2004
4 Raju BG, Ciabatti R, Maffioli SI, Singh U, Romano G, Michelucci E, Tiseni PS, Candiani G, Kim B, O’Dowd H. US 20060211603, 2006

5a Vaillard VA, Rossi RA, Martín SE. Org. Biomol. Chem. 2011; 9: 4927
5b Vaillard VA, Guastavino JF, Budén ME, Bardagí JI, Barolo SM, Rossi RA. J. Org. Chem. 2012; 77: 1507

6 Gooßen LJ, Rodríguez N, Gooßen K. Angew. Chem. Int. Ed. 2008; 47: 3100
7 Akiyoshi M, Yumi N, Hiroyuki N, Kouichi U, Toshiharu O. Bioorg. Med. Chem. Lett. 2008; 18: 782
8 Harjani JR, Tang AX, Norton RS, Baell JB. Tetrahedron 2014; 70: 8047
9 Dai J.-J, Liu J.-H, Luo D.-F, Liu L. Chem. Commun. 2011; 47: 677

10a Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
10b Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
10c Xiao Z.-C, Xia C.-F. Youji Huaxue 2013; 33: 2119

11a Collins BS. L, Suero MG, Gaunt MJ. Angew. Chem. Int. Ed. 2013; 52: 5799
11b Peng J, Chen C, Wang Y, Lou Z.-B, Li M, Xi C.-J, Chen H. Angew. Chem. Int. Ed. 2013; 52: 7574
11c Guo J, Dong S.-X, Zhang Y.-L, Kuang Y.-L, Liu X.-H, Lin L.-L, Feng X.-M. Angew. Chem. Int. Ed. 2013; 52: 10245
11d Ho JS, Castro LC. M, Aihara Y, Tobisu M, Chatani N. Asian J. Org. Chem. 2014; 3: 48
11e Su X, Chen C, Wang Y, Chen J.-J, Lou Z.-B, Li M. Chem. Commun. 2013; 49: 6752
11f Hu R.-B, Zhang H, Zhang X.-Y, Yang S.-D. Chem. Commun. 2014; 50: 2193
11g Suero MG, Bayle ED, Collins BS. L, Gaunt MJ. J. Am. Chem. Soc. 2013; 135: 5332
11h Xu Q-L, Gao H.-Y, Yousufuddin M, Ess DH, Kurti L. J. Am. Chem. Soc. 2013; 135: 14048
11i Lv T.-Y, Wang Z, You J.-S, Lan J.-B, Gao G. J. Org. Chem. 2013; 78: 5723
11j Wagner AM, Sanford MS. J. Org. Chem. 2014; 79: 2263
11k Umierski N, Manolikakes G. Org. Lett. 2013; 15: 188
11l Gigant N, Boissarie LC, Belhomme MC, Poisson T, Pannecoucke X, Gillaizeau I. Org. Lett. 2013; 15: 278
11m Guo F.-L, Han J.-W, Mao S, Li J, Geng X, Yu J.-J, Wang L.-M. RSC Adv. 2013; 3: 6267
11n Bhong BY, Shelke AV, Karade NN. Tetrahedron Lett. 2013; 54: 739
11o Cullen SC, Shekhar S, Nere NK. J. Org. Chem. 2013; 78: 12194

12a Prakash M, Muthusamy S, Kesavan V. J. Org. Chem. 2014; 79: 7836
12b Li P, Cheng G, Zhang H, Xu X, Gao J, Cui X. J. Org. Chem. 2014; 79: 8156

13a Malmgren J, Nagendiran A, Tai CW, Backvall JE, Olofsson B. Chem. Eur. J. 2014; 20: 13531
13b Petersen TB, Khan R, Olofsson B. Org. Lett. 2011; 13: 3462

14 Zhang F.-Z, Das S, Walkinshaw AJ, Casitas A, Taylor M, Suero MG, Gaunt MJ. J. Am. Chem. Soc. 2014; 136: 8851
15 Modha SG, Greaney MF. J. Am. Chem. Soc. 2015; 137: 1416
16 Matsuzaki K, Okuyama K, Tokunaga E, Saito N, Shiro M, Shibata N. Org. Lett. 2015; 17: 3038

17a Chen J, Chen C, Chen J.-J, Wang G.-H, Qu H.-M. Chem. Commun. 2015; 51: 1356
17b Guo W, Li S.-L, Tang L, Li M, Wen L.-R, Chen C. Org. Lett. 2015; 17: 1232
17c Pang X.-L, Chen C, Su X, Li M, Wen L.-R. Org. Lett. 2014; 16: 6228

18 Jiang H, Cheng Y.-Z, Wang R.-Z, Zhang Y, Yu S.-Y. Chem. Commun. 2014; 50: 6164
19 Bhattarai B, Tay JH, Nagorny P. Chem. Commun. 2015; 51: 5398
20 Iyanaga M, Aihara Y, Chatani N. J. Org. Chem. 2014; 79: 11933
21 Monastyrskyi A, Namelikonda NK, Manetsch R. J. Org. Chem. 2015; 80: 2513
22 Sundalam SK, Stuart DR. J. Org. Chem. 2015; 80: 6456

23a Ichiishi N, Canty AJ, Yates BF, Sanford MS. Organometallics 2014; 33: 5525
23b Kumar D, Pilania M, Arun V, Pooniya S. Org. Biomol. Chem. 2014; 12: 6340
23c Li J, Wang H.-N, Sun J.-T, Yang Y, Liu L. Org. Biomol. Chem. 2014; 12: 7904

For selected papers from our group, see:

24a Wang D, Ge B, Li L, Shan J, Ding Y. J. Org. Chem. 2014; 79: 8607
24b Wang D, Yu X, Zhao K, Li L, Ding Y. Tetrahedron Lett. 2014; 55: 5739
24c Wang D, Zhao K, Xu C, Miao H, Ding Y. ACS Catal. 2014; 4: 3910
24d Chen J, Zhao K, Ge B, Xu C, Wang D, Ding Y. Chem. Asian J. 2015; 10: 468
24e Wang D, Yu X, Yao W, Hu W, Ge C, Shi X. Chem. Eur. J. 2016; 22: 5543
24f Yang Y, Qin A, Zhao K, Wang D, Shi X. Adv. Synth. Catal. 2016; 358: 1443
24g Wang D, Yu X, Xu X, Ge B, Wang X, Zhang Y. Chem. Eur. J. 2016; 22: 8663

25a Miller WH. WO 2001027103, 2001
25b An J, Chang N.-J, Song L.-D, Jin Y.-Q, Ma Y, Chen JR, Xiao W.-J. Chem. Commun. 2011; 47: 1869

26a Bao Y.-S, Baiyin M, Agula B, Jia M, Zhaorigetu B. J. Org. Chem. 2014; 79: 6715
26b Bissantz C. WO 2007009906, 2007
26c Brooks G, Hunt E. WO 2000037074, 2000
26d Boatman RJ, Whitlock HW. J. Org. Chem. 1976; 41: 3050

27 Neagoie C, Vedrenne E, Buron F, Mérour J.-Y, Rosca S, Bourg S, Lozach O, Meijer L, Baldeyrou B, Lansiaux A, Routier S. Eur. J. Med. Chem. 2012; 49: 379

28a Malmgren J, Santoro S, Jalalian N, Himo F, Olofsson B. Chem. Eur. J. 2013; 19: 10334
28b de Magalhāes HP, Lüthi HP, Togni A. Org. Lett. 2012; 14: 3830

29 Typical Procedure for the Synthesis of 3a Ph₂IOTf (0.6 mmol) and toluene (2 mL) were stirred in a Schlenk tube at room temperature for a moment. Subsequently, 1H-indole-2-carboxylic acid (1a, 0.5 mmol) and K₂CO₃ (0.75 mmol) was added. The mixture was heated under 130 °C for 12 h and then cooled to room temperature. The resulting solution was directly purified by column chromatography with PE–EtOAc (5:1) as eluent to give phenyl 1H-indene-2-carboxylate (3a) as a yellow solid in 84% yield. ¹H NMR (600 MHz, CDCl₃): δ = 9.42 (s, 1 H), 7.77 (d, J = 8.0 Hz, 1 H), 7.48 (d, J = 8.2 Hz, 3 H), 7.39–7.33 (m, 3 H), 7.31–7.26 (m, 2 H), 7.21 (m, 1 H). ¹³C NMR (151 MHz, CDCl₃): δ = 160.77, 150.45, 137.42, 129.56, 127.37, 126.31, 126.10, 125.88, 122.77, 121.71, 121.01, 112.12, 110.27.

Zusatzmaterial

Supporting Information