Synthesis of Triazole-Fused Phenanthridines through Pd-Catalyzed Intramolecular Phenyl C–H Activation of 1,5-Diaryl-1,2,3-triazoles

Jiazhuang Wang; Jianhua Yang; Xuxin Fu; Guiping Qin; Tiebo Xiao; Yubo Jiang

doi:10.1055/s-0037-1611859

Synlett, Table of Contents

Synlett 2019; 30(12): 1452-1456
DOI: 10.1055/s-0037-1611859

letter

Synthesis of Triazole-Fused Phenanthridines through Pd-Catalyzed Intramolecular Phenyl C–H Activation of 1,5-Diaryl-1,2,3-triazoles

Jiazhuang Wang

,

Jianhua Yang

,

Xuxin Fu

,

Guiping Qin

,

Tiebo Xiao∗

Faculty of Science, Kunming University of Science and Technology, South Jingming Road 727, Kunming 650500, P. R. of China Email: xiaotb@kmust.edu.cn Email: ybjiang@kmust.edu.cn

,

Yubo Jiang∗

Faculty of Science, Kunming University of Science and Technology, South Jingming Road 727, Kunming 650500, P. R. of China Email: xiaotb@kmust.edu.cn Email: ybjiang@kmust.edu.cn

› Author Affiliations

Abstract

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^§Both authors contributed equally.

Abstract

An efficient method for the synthesis of triazole-fused phenanthridines from 1,5-diaryl-1,2,3-triazoles under palladium catalysis has been developed. The reaction proceeds through Pd-catalyzed intramolecular phenyl C–H activation of 1,5-diaryl-1,2,3-triazoles. This method provides a concise and efficient pathway to construct triazolo[1,5-f]phenanthridine derivatives in excellent yields.

Key words

palladium catalyst - site-selective reactions - C–H activation - 1,5-diaryl-1,2,3-triazoles - fused phenanthridines

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References

References and Notes
1 Pictet A, Ankersmit HJ. Justus Liebigs Ann. Chem. 1891; 266: 138
2 Calder E, McGonagle F, Harkiss A, McGonagle G, Sutherland A. J. Org. Chem. 2014; 79: 7633

3a Cheng P, Qing Z, Liu S, Liu W, Xie H, Zeng J. Tetrahedron Lett. 2014; 55: 6647
3b Lasák P, Motyka K, Kryštof V, Stýskala J. Molecules 2018; 23: 2155
3c Steinhauer T, Girreser U, Meier C, Cushman M, Clement B. Chem. Eur. J. 2016; 22: 8301

4a Zhao D, Tang X, Liu X, Fan J, Liao L. Org. Electron. 2017; 50: 473
4b Liu M, Liang Y, Chen P, Chen D, Liu K, Li Y, Liu S, Gong X, Huang F, Su S, Cao Y. J. Mater. Chem. A 2014; 2: 321
4c Yuvaraj AR, Renjith Anu. Kumar S. 2018; 272: 583
4d Balijapalli U, Udayadasan S, Shanmugam E, Kulathu Iyer S. Dyes Pigm. 2016; 130: 233

5a Wu D, Fang B, Zhang M, Du W, Zhang J, Tian X, Zhang Q, Zhou H, Wu J, Tian Y. Dyes Pigm. 2018; 159: 142
5b Chen H, Long H, Cui X, Zhou J, Xu M, Yuan G. J. Am. Chem. Soc. 2014; 136: 2583

6a Romo-Pérez A, Miranda L, García A. Tetrahedron Lett. 2015; 56: 6669
6b Strmiskova M, Bilodeau D, Chigrinova M, Pezacki J. Can. J. Chem. 2019; 97: 1

7a Rafiee F. Appl. Organomet. Chem. 2017; 31: 3820
7b Sun X, Yu S. Org. Lett. 2014; 16: 2938
7c Cheng Y, Jiang H, Zhang Y, Yu S. Org. Lett. 2013; 15: 5520
7d Jiang H, Cheng Y, Wang R, Zheng M, Zhang Y, Yu S. Angew. Chem. Int. Ed. 2013; 52: 13289
7e Cai J, Hu Z, Li Y, Liu J, Xu X. Adv. Synth. Catal. 2018; 360: 3595
7f Zhu Z, Chen K, Xu Q, Shi M. Adv. Synth. Catal. 2015; 357: 3081
7g Fan-Chiang T.-T, Wang H.-K, Hsieh J.-C. Tetrahedron 2016; 72: 5640
7h Elsayeda M, Zellerb M, Cushman M. Synth. Commun. 2016; 46: 1902
7i Mehrabi H, Pishahang J. Synth. Commun. 2014; 44: 76

8a Wang X, Huang B, Liu X, Zhan P. Drug Discovery Today 2016; 21: 118
8b Bua S, Osman S, Del Prete S, Capasso C, AlOthman Z, Nocentini A, Supuran C. Bioorg. Chem. 2019; 86: 183
8c Song M, Deng X. J. Enzym. Inhib. Med. Chem. 2018; 33: 453
8d Shiva Raju K, AnkiReddy S, Sabitha G, Siva KVagolu, Siram D, Bharathi ReddyK, Rao SagurthiS. Bioorg. Med. Chem. Lett. 2019; 29: 284
8e Thanh N, Hai D, Ngoc Bich V, Thu Hien P, Ky Duyen N, Mai N, Dung T, Toan V, Kim Van H, Dang L, Toan D, Thanh Van T. Eur. J. Med. Chem. 2019; 167: 454
8f Faidallah H, Panda S, Serrano J, Girgis A, Khan K, Alamry K, Therathanakorn T, Meyers M, Sverdrup F, Eickhoff C, Getchell S, Katritzky A. Bioorg. Med. Chem. 2016; 24: 3527
8g Niu C, Lu X, Aisa H. RSC Adv. 2019; 9: 1671
8h Krawczyk M, Pastuch-Gawolek G, Mrozek-Wilczkiewicz A, Kuczak M, Skonieczna M, Musiol R. Bioorg. Chem. 2019; 84: 326

9a Liu Yi, He C, Tang Y, Imler G, Parrish D, Shreeve J. Dalton Trans. 2019; 48: 3237
9b Peng R, Xu Y, Cao Q. Chin. Chem. Lett. 2018; 29: 1465
9c He M, Li W, Tian H, Tong H, Zhang J, Liu J, Xie Z, Geng Y, Wang F. Org. Electron. 2019; 65: 31
9d Tanimu A, Jillani S, Alluhaidan A, Ganiyu S, Alhooshani K. Talanta 2019; 194: 377
9e Nguyen M, Byun J, Kim S, Hyun J, Hur K, Shin T, Cho B. Angew. Chem. Int. Ed. 2019; 58: 2749
9f Li P, Wang X, Zhao Y. Coord. Chem. Rev. 2019; 380: 484

10a Sadjadi S, Heravi M, Malmir M, Noritajer F. Mater. Chem. Phys. 2019; 223: 380
10b Zurro M, Mancheno O. Chem. Rec. 2017; 17: 485
10c Hosseinnejad T, Ebrahimpour-Malmir F, Fattahi B. RSC Adv. 2018; 8: 12232
10d Chen A, Samankumara L, Dodlapati S, Wang D, Adhikari S, Wang G. Eur. J. Org. Chem. 2019; 1189
10e Guisado-Barrios G, Soleilhavoup M, Bertrand G. Acc. Chem. Res. 2018; 51: 3236
10f Wang Z, Li B, Zhang X, Fan X. J. Org. Chem. 2016; 81: 6357
10g Gangaprasad D, Paul Raj J, Karthikeyan K, Rengasamy R, Elangovan J. Adv. Synth. Catal. 2018; 360: 4485
10h Pericherla K, Jha A, Khungar B, Kumar A. Org. Lett. 2013; 15: 4304

11a Johansson J, Beke-Somfai T, Stålsmeden A, Kann N. Chem. Rev. 2016; 116: 14726
11b Alonso F, Moglie Y, Radivoy G. Acc. Chem. Res. 2015; 48: 2516
11c Hein J, Fokin V. Chem. Soc. Rev. 2010; 39: 1302
11d Rostovtsev V, Green L, Fokin V, Sharpless K. Angew. Chem. Int. Ed. 2002; 41: 2596

12a Johansson J, Beke-Somfai T, Stalsmeden A, Kann N. Chem. Rev. 2016; 116: 14726
12b Hosseinnejad T, Mandavian S. Comput. Theor. Chem. 2018; 1143: 29
12c Liu P, Clark R, Zhu L. J. Org. Chem. 2018; 83: 5092
12d Engholm E, Stuhr-Hansen N, Blixt O. Tetrahedron Lett. 2017; 58: 2272
12e Boren B, Narayan S, Rasmussen L, Zhang L, Zhao H, Lin Z, Jia G, Fokin V. J. Am. Chem. Soc. 2008; 130: 8923

13a Ackermann L, Althammer A, Born R. Angew. Chem. Int. Ed. 2006; 45: 2619
13b Zhao F, Liu Y, Yang S, Xie K, Jiang Y. Org. Chem. Front. 2017; 4: 1112
13c Gu Q, Al Mamari H, Grczyk K, Diers E, Ackermann L. Angew. Chem. Int. Ed. 2014; 53: 3868
13d Shang R, Ilies L, Nakamura E. Chem. Rev. 2017; 117: 9086
13e Bauer M, Wang W, Lorion M, Dong C, Ackermann L. Angew. Chem. Int. Ed. 2018; 57: 203
13f He P, Tian Q, Kuang C. Org. Biomol. Chem. 2015; 13: 7146
13g Fruchey E, Monks B, Cook S. J. Am. Chem. Soc. 2014; 136: 13130
13h Wang Z, Tian Q, Yu X, Kuang C. Adv. Synth. Catal. 2014; 356: 961
13i Zhao F, Chen Z, Ma X, Huang S, Jiang Y. Tetrahedron Lett. 2017; 58: 614
13j Shi S, Kuang C. J. Org. Chem. 2014; 79: 6105
13k Wang Z, Kuang C. Adv. Synth. Catal. 2014; 356: 1549
13l Tian Q, Chen X, Liu W, Wang Z, Shi S, Kuang C. Org. Biomol. Chem. 2013; 11: 7830

14 Liu Z, Zhu D, Luo B, Zhang N, Liu Q, Hu Y, Pi R, Huang P, Wen S. Org. Lett. 2014; 16: 5600
15 Kumara A, Shindea S, Tiwaria D, Sridharb B, Likhar P. RSC Adv. 2016; 6: 43638
16 Wang Q, Shi X, Zhang X, Fan X. Org. Biomol. Chem. 2017; 15: 8529
17 Hadj Mokhtar H, Laidaoui N, El Abed D, Soule J, Doucet H. Catal. Commun. 2017; 92: 124
18 CCDC 1857225 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.
19 Synthesis of Triazolophenanthridines 2; General Procedure To a 50 mL pressure tube, 1,5-diaryl-1,2,3-triazole were added 1 (0.3 mmol), Pd(OAc)₂ (0.03 mmol), PCy₃ (0.06 mmol), CsOPiv (0.9 mmol), and toluene (2 mL) and the reaction mixture was stirred at 130 °C for 24 h. After consumption of the 1,5-disubstitued 1,2,3-triazoles monitored by TLC analysis, the mixture was treated with H₂O (15 mL) and extracted with EtOAc (3 × 15 mL). The combined organic layers were washed with brine (3 × 5 mL), dried with Na₂SO₄, and concentrated under reduced pressure to afford a crude product. Purification by column chromatography on silica gel with EtOAc-PE (1:8) afforded the desired products 2.9-Methyl-[1,2,3]triazolo[1,5-f]phenanthridine (2a)White solid; yield: 65 mg (93%); mp 159.8–160.8 °C. IR (KBr): 3066, 2946, 2841, 1731, 1620, 1555, 1494, 1448, 1207, 1124, 1074, 1014, 826, 760, 584 cm^–1. ¹H NMR (600 MHz, CDCl₃): δ = 8.64 (d, J = 8.4 Hz, 1 H), 8.39 (s, 1 H), 8.35 (d, J = 8.0 Hz, 1 H), 8.16 (s, 1 H), 8.10–8.03 (m, 1 H), 7.69–7.63 (m, 1 H), 7.61 (dd, J = 10.8, 4.1 Hz, 1 H), 7.51 (d, J = 8.3 Hz, 1 H), 2.58 (s, 3 H). ¹³C NMR (150 MHz, CDCl₃): δ = 137.3, 131.3, 130.8, 129.2, 129.0, 128.6, 127.3, 127.2, 124.8, 123.5, 123.0, 121.9, 121.9, 116.9, 21.7. HRMS (ESI⁺): m/z [M + H]⁺ calcd for C₁₅H₁₂N₃: 234.1026; found: 234.1031.[1,2,3]Triazolo[1,5-f]phenanthridine (2b)White solid; yield: 62 mg (95%); mp 187.2–188.4 °C. IR (KBr): 3047, 2944, 2843, 1944, 1790, 1724, 1617, 1558, 1447, 1220, 1125, 976, 822, 747, 526 cm^–1. ¹H NMR (600 MHz, CDCl₃): δ = 8.75–8.73 (m, 1 H), 8.39–8.37 (m, 1 H), 8.36–8.33 (m, 1 H), 8.32–8.30 (m, 1 H), 8.04–8.01 (m, 1 H), 7.71–7.67 (m, 1 H), 7.65–7.57 (m, 3 H). ¹³C NMR (150 MHz, CDCl₃): δ = 131.4, 130.8, 129.5, 129.3, 128.6, 127.3, 127.2, 127.1, 124.6, 123.5, 122.9, 121.9, 121.6, 117.0. HRMS (ESI⁺): m/z [M + H]⁺ calcd for C₁₄H₁₀N₃: 220.0869; found: 220.0872.11-Methyl-[1,2,3]triazolo[1,5-f]phenanthridine (2c)White solid; yield: 60 mg (86%); mp 142.1–143 °C. IR (KBr): 3045, 2948, 2849, 1957, 1786, 1710, 1623, 1564, 1512, 1449, 1393, 1226, 1126, 1079, 971, 854, 810, 756, 566 cm^–1. ¹H NMR (600 MHz, CDCl₃): δ = 8.39 (dd, J = 3.0, 1.5 Hz, 1 H), 8.34 (t, J = 8.2 Hz, 1 H), 8.28 (t, J = 7.8 Hz, 1 H), 8.04 (dd, J = 9.2, 4.6 Hz, 1 H), 7.64–7.57 (m, 2 H), 7.52 (d, J = 2.7 Hz, 1 H), 7.50–7.46 (m, 1 H), 3.17 (s, 3 H). ¹³C NMR (150 MHz, CDCl₃): δ = 133.2, 132.5, 132.5, 130.7, 130.3, 129.2, 128.5, 127.9, 126.5, 125.9, 124.3, 123.3, 123.2, 121.7, 121.3, 25.2. HRMS (ESI⁺): m/z [M + H]⁺ calcd for C₁₅H₁₂N₃: 234.1026; found: 234.1029.

Supplementary Material