Facile Construction of Troponoid Derivatives Incorporating Imidazolin-2-one Moieties

Jing Yu; Xiaobei Chen; Ye Liu; Bing Wu; Haiyan Li; Yanwei Hu; Liang Wang; Shilei Zhang

doi:10.1055/s-0040-1708006

Synthesis, Table of Contents

Synthesis 2020; 52(12): 1847-1854
DOI: 10.1055/s-0040-1708006

paper

Facile Construction of Troponoid Derivatives Incorporating Imidazolin-2-one Moieties

Authors

Jing Yu‡

^aJiangsu Key Laboratory of Neuropsychiatric Diseases & College of Pharmaceutical Sciences, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu, 215123, P. R. of China Email: huyanwei@suda.edu.cn Email: zhangshilei@suda.edu.cn
Xiaobei Chen‡

^bState Key Laboratory of Bioengineering Reactor, and Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science & Technology, Shanghai 200237, P. R. of China
Ye Liu

^aJiangsu Key Laboratory of Neuropsychiatric Diseases & College of Pharmaceutical Sciences, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu, 215123, P. R. of China Email: huyanwei@suda.edu.cn Email: zhangshilei@suda.edu.cn
Bing Wu

^dCollege of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu, 215123, P. R. of China
Haiyan Li

^dCollege of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu, 215123, P. R. of China
Yanwei Hu∗

^aJiangsu Key Laboratory of Neuropsychiatric Diseases & College of Pharmaceutical Sciences, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu, 215123, P. R. of China Email: huyanwei@suda.edu.cn Email: zhangshilei@suda.edu.cn
Liang Wang∗

^cCollege of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, P. R. of China Email: liangwang0532@yeah.net
Shilei Zhang∗

^aJiangsu Key Laboratory of Neuropsychiatric Diseases & College of Pharmaceutical Sciences, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu, 215123, P. R. of China Email: huyanwei@suda.edu.cn Email: zhangshilei@suda.edu.cn

Abstract

All articles of this category

Abstract

Troponoid derivatives incorporating imidazolin-2-one moieties were efficiently constructed via a cascade process, under simple thermal conditions, which features a novel nitrogen source, is catalyst- and oxidant-free, and has high atom- and step-economy.

Key words

troponoid - isocyanate - imidazolin-2-one - cascade reaction - high temperature

Full Text

References

References
1 Zhu Y, Cornwall RG, Du H, Zhao B, Shi Y. Acc. Chem. Res. 2014; 47: 3665

2a Fukudome Y, Naito H, Hata T, Urabe H. J. Am. Chem. Soc. 2008; 130: 1820
2b Rajesh M, Puri S, Kant R, Reddy MS. J. Org. Chem. 2017; 82: 5169

3a Robain A, Perchet H, Fuhrman C. Acta Cardiol. 2000; 55: 45
3b Mehra D, Imtiaz MS, van Helden DF, Knollmann BC, Laver DR. Mol. Pharmacol. 2014; 86: 696
3c Yang S, Ren Z, Chen M, Wang Y, You B, Chen W, Qu C, Liu Y, Zhang X. Mol. Pharm. 2018; 15: 314
3d Reich MR, Govindaraj R. Health Policy 1998; 44: 1
3e Fenwick A, Keiser J, Utzinger J. Drugs Future 2006; 31: 413
3f Pan J.-E, Xiong F.-L, Chen G, Zhang Z.-W, Xu Y.-J. Biomed. Pharmacother. 2017; 95: 1549
3g Wang M, Wang M, Zhang Q, Zong S, Lv C. Eur. J. Drug Metab. Pharmacokinet. 2018; 43: 405

4a Doyle AG, Jacobsen EN. Chem. Rev. 2007; 107: 5713
4b Taylor MS, Jacobsen EN. Angew. Chem. Int. Ed. 2006; 45: 1520

5a Zhao B, Du H, Cui S, Shi Y. J. Am. Chem. Soc. 2010; 132: 3523
5b Ramirez TA, Wang Q, Zhu Y, Zheng H, Peng X, Cornwall RG, Shi Y. Org. Lett. 2013; 16: 4210
5c Zhao B, Peng X, Cui S, Shi Y. J. Am. Chem. Soc. 2010; 132: 11009
5d Zhao B, Peng X, Zhu Y, Ramirez TA, Cornwall RG, Shi Y. J. Am. Chem. Soc. 2011; 133: 20890
5e Zhang H, Pu W, Xiong T, Li Y, Zhou X, Sun K, Liu Q, Zhang Q. Angew. Chem. Int. Ed. 2013; 52: 2529
5f Shen K, Wang Q. Chem. Sci. 2015; 6: 4279
5g Zhu Y, Shi Y. Chem. Eur. J. 2014; 20: 13901

6a Roben C, Souto JA, Gonzalez Y, Lishchynskyi A, Muniz K. Angew. Chem. Int. Ed. 2011; 50: 9478
6b Hong KB, Johnston JN. Org. Lett. 2014; 16: 3804
6c Chen H, Kaga A, Chiba S. Org. Lett. 2014; 16: 6136
6d Danneman MW, Hong KB, Johnston JN. Org. Lett. 2015; 17: 3806

7a Guchhait SK, Hura N, Shah AP. J. Org. Chem. 2017; 82: 2745
7b Mizar P, Laverny A, El-Sherbini M, Farid U, Brown M, Malmedy F, Wirth T. Chem. Eur. J. 2014; 20: 9910

8a Zabawa TP, Kasi D, Chemler SR. J. Am. Chem. Soc. 2005; 127: 11250
8b Muniz K, Hovelmann CH, Streuff J. J. Am. Chem. Soc. 2008; 130: 763
8c Muniz K, Martinez C. J. Org. Chem. 2013; 78: 2168

9a Wu Z, Wen K, Zhang J, Zhang W. Org. Lett. 2017; 19: 2813
9b Danneman MW, Hong KB, Johnston JN. Org. Lett. 2015; 17: 2558

10a Sequeira FC, Turnpenny BW, Chemler SR. Angew. Chem. Int. Ed. 2010; 49: 6365
10b Sibbald PA, Rosewall CF, Swartz RD, Michael FE. J. Am. Chem. Soc. 2009; 131: 15945
10c Ingalls EL, Sibbald PA, Kaminsky W, Michael FE. J. Am. Chem. Soc. 2013; 135: 8854

11a Wang Y.-F, Zhu X, Chiba S. J. Am. Chem. Soc. 2012; 134: 3679
11b Zhang J, Zhang G, Wu W, Zhang X, Shi M. Chem. Commun. 2014; 50: 15052

12a Du H, Zhao B, Shi Y. J. Am. Chem. Soc. 2007; 129: 762
12b Du H, Zhao B, Shi Y. J. Am. Chem. Soc. 2008; 130: 8590

13 Yuan YA, Lu DF, Chen YR, Xu H. Angew. Chem. Int. Ed. 2016; 55: 534

14a Carling RW, Moore KW, Moyes CR, Jones EA, Bonner K, Emms F, Marwood R, Patel S, Patel S, Fletcher AE, Beer M, Sohal B, Pike A, Leeson PD. J. Med. Chem. 1999; 42: 2706
14b Bronson JJ, DenBleyker KL, Falk PJ, Mate RA, Ho H.-T, Pucci MJ, Snyder LB. Bioorg. Med. Chem. Lett. 2003; 13: 873
14c Shaw AW, Paone DV, Nguyen DN, Stump CA, Burgey CS, Mosser SD, Salvatore CA, Rutledge RZ, Kane SA, Koblan KS, Graham SL, Vacca JP, Williams TM. Bioorg. Med. Chem. Lett. 2007; 17: 4795
14d Xue N, Yang X, Wu R, Chen J, He Q, Yang B, Lu X, Hu Y. Bioorg. Med. Chem. 2008; 16: 2550

15a Proulx C, Lubell WD. Org. Lett. 2012; 14: 4552
15b Peshkov VA, Pereshivko OP, Sharma S, Meganathan T, Parmar VS, Ermolat’ev DS, Van der Eycken EV. J. Org. Chem. 2011; 76: 5867
15c Zhao B, Du H, Shi Y. J. Org. Chem. 2009; 74: 4411
15d Verniest G, Padwa A. Org. Lett. 2008; 10: 4379
15e Siamaki AR, Black DA, Arndtsen BA. J. Org. Chem. 2008; 73: 1135
15f Lee S.-H, Yoshida K, Matsushita H, Clapham B, Koch G, Zimmermann J, Janda KD. J. Org. Chem. 2004; 69: 8829

16 Engels HW, Pirkl HG, Albers R, Albach RW, Krause J, Hoffmann A, Casselmann H, Dormish J. Angew. Chem. Int. Ed. 2013; 52: 9422

17a Han J, Wang N, Huang ZB, Zhao Y, Shi DQ. J. Org. Chem. 2017; 82: 6831
17b Allen MA, Ivanovich RA, Polat DE, Beauchemin AM. Org. Lett. 2017; 19: 6574
17c Meloche JL, Ashfeld BL. Angew. Chem. Int. Ed. 2017; 56: 6604
17d Rajesh M, Puri S, Kant R, Reddy MS. Org. Lett. 2016; 18: 4332
17e Schafer G, Matthey C, Bode JW. Angew. Chem. Int. Ed. 2012; 51: 9173

18a Fischer G. Adv. Heterocycl. Chem. 1996; 66: 285
18b Zhao J. Curr. Med. Chem. 2007; 14: 2597
18c Liu N, Song W, Schienebeck CW, Zhang M, Tang W. Tetrahedron 2014; 70: 9281

19a Yu P, He CQ, Simon A, Li W, Mose R, Thøgersen MK, Jørgensen KA, Houk KN. J. Am. Chem. Soc. 2018; 140: 13726
19b Murarka S, Jia Z.-J, Merten C, Daniliuc C.-G, Antonchick AP, Waldmann H. Angew. Chem. Int. Ed. 2015; 54: 7653
19c Teng H.-L, Yao L, Wang C.-J. J. Am. Chem. Soc. 2014; 136: 4075
19d Liu H, Wu Y, Zhao Y, Li Z, Zhang L, Yang W, Jiang H, Jing C, Yu H, Wang B, Xiao Y, Guo H. J. Am. Chem. Soc. 2014; 136: 2625
19e Thangaraj M, Bhojgude SS, Bisht RH, Gonnade RG, Biju AT. J. Org. Chem. 2014; 79: 4757
19f Li P, Yamamoto H. J. Am. Chem. Soc. 2009; 131: 16628
19g Trost BM, McDougall PJ, Hartmann O, Wathen PT. J. Am. Chem. Soc. 2008; 130: 14960
19h Du Y, Feng J, Lu X. Org. Lett. 2005; 7: 1987
19i Constantino MG, De Oliveira KT, Beatriz A, Da Silva GV. J. Tetrahedron Lett. 2003; 44: 2641

20a Mose R, Preegel G, Larsen J, Jakobsen S, Iversen EH, Jørgensen KA. Nat. Chem. 2017; 9: 487
20b Liu HL, Jia H, Shi WY, Wang C, Zhang C, Guo HC. Org. Lett. 2018; 20: 3570
20c Jia S, Su S, Li C, Jia X, Li J. Org. Lett. 2014; 16: 5604
20d Esteban F, Alfaro R, Yuste F, Parra A, Ruano JL. G, Alemán J. Eur. J. Org. Chem. 2014; 1395
20e Tejero R, Ponce A, Adrio J, Carretero JC. Chem. Commun. 2013; 49: 10406
20f Rivero AR, Fernandez I, Sierra MA. Org. Lett. 2013; 15: 4928
20g Nair V, Poonoth M, Vellalath S, Suresh E, Thirumalai R. J. Org. Chem. 2006; 71: 8964

21a Kikuchi K, Maki Y, Sato K. Bull. Chem. Soc. Jpn. 1978; 51: 2338
21b Rigby JH, Senanayake CH, Rege S. J. Org. Chem. 1988; 53: 4596
21c Naya S.-i, Nitta M. Tetrahedron 2003; 59: 3709
21d Coskun A, Güney M, Dastan A, Balci M. Tetrahedron 2007; 63: 4944
21e Nair V, Abhilash KG, Suresh E. Tetrahedron Lett. 2006; 47: 9329

22a Liu T, Li Q, Wei L, Xiong Y, Wang C. Adv. Synth. Catal. 2017; 359: 1854
22b Ito K, Saito K, Takahashi K. Heterocycles 1992; 34: 2339
22c Ito K, Hara Y, Sakakibara R, Saito K. Heterocycles 1995; 41: 1675
22d Kajigaeshi S, Matsuoka S, Kanemasa S, Noguchi M. J. Heterocycl. Chem. 1986; 23: 49
22e Kikuo Y, Shoji K, Shuji K. Chem. Lett. 1977; 6: 85

23 In reference 22e the reaction of tropone-based imine C and isocyanate was reported; this generated compound 3 but not 4 as the product, as shown in Scheme 3.

24a Jiang J, Cai X, Hu Y.-W, Liu X.-J, Chen X.-D, Wang S.-Y, Zhang Y.-N, Zhang S.-L. J. Org. Chem. 2019; 84: 2022
24b Sun WW, Mao YJ, Jiang J, Yu J, Chen LY, Hu YW, Zhang SL. Chin. J. Org. Chem. 2019; 39: 2525

25 CCDC 1821619 (4a) 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.

Supplementary Material

Supporting Information (PDF) (opens in new window)