Facile Synthesis of Spirocyclic Tetrahydroquinolines via C(sp3)–H Functionalization in a Cascade Redox Process

Liping Yu; Bin Qiu; Peizhen Dong; Jian Xiao; Shitao Yu

doi:10.1055/s-0040-1720890

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(05): 1309-1320
DOI: 10.1055/s-0040-1720890

paper

Facile Synthesis of Spirocyclic Tetrahydroquinolines via C(sp³)–H Functionalization in a Cascade Redox Process

Liping Yu

^aCollege of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. of China

^cCollege of Landscape and Forestry, Qingdao Agricultural University, Qingdao 266109, P. R. of China

,

Bin Qiu

^bCollege of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, P. R. of China

,

Peizhen Dong

^bCollege of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, P. R. of China

,

Jian Xiao∗

^bCollege of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, P. R. of China

,

Shitao Yu∗

^aCollege of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. of China

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

An environmentally benign cascade redox process was developed for the efficient construction of the pharmaceutically significant spirocyclic tetrahydroquinolines via sequential S_NAr/Knoevenagel condensation/[1,5]-hydride transfer/cyclization. This green transformation has the features of being catalyst-free, additive-free, operationally simple, and has high step- and atom-economy.

Key words

tetrahydroquinoline - C–H functionalization - cascade reaction - hydride transfer

Volltext

Referenzen

References

1a Ruble JC, Hurd AR, Johnson TA, Sherry DA, Barbachyn MR, Toogood PL, Bundy GL, Graber DR, Kamilar GM. J. Am. Chem. Soc. 2009; 131: 3991
1b Basarab GS, Brassil P, Doig P, Galullo V, Haimes HB, Kern G, Kutschke A, McNulty J, Schuck VJ. A, Stone G, Gowravaram M. J. Med. Chem. 2014; 57: 9078
1c Basarab GS, Doig P, Galullo V, Kern G, Kimzey A, Kutschke A, Newman JP, Morningstar M, Mueller J, Otterson L, Vishwanathan K, Zhou F, Gowravaram M. J. Med. Chem. 2015; 58: 6264
1d Chan PF, Srikannathasan V, Huang J, Cui H, Fosberry AP, Gu M, Hann MM, Hibbs M, Homes P, Ingraham K, Pizzollo J, Shen C, Shillings AJ, Spitzfaden CE, Tanner R, Theobald AJ, Stavenger RA, Bax BD, Gwynn MN. Nat. Commun. 2015; 6: 10048

2a Yu D, Suzuki M, Xie L, Morris-Natschke SL, Lee KH. Med. Res. Rev. 2003; 23: 322
2b Xue H, Lu X, Zheng P, Liu L, Han C, Hu J, Liu Z, Ma T, Li Y, Wang L, Chen Z, Liu G. J. Med. Chem. 2010; 53: 1397

3a Kodanko JJ, Overman LE. Angew. Chem. Int. Ed. 2003; 42: 2528
3b Garg NK, Hiebert S, Overman LE. Angew. Chem. Int. Ed. 2006; 45: 2912
3c Steven A, Overman LE. Angew. Chem. Int. Ed. 2007; 46: 5488
3d Codelli JA, Puchlopek AL, Reisman SE. J. Am. Chem. Soc. 2012; 134: 1930
3e Kieffer ME, Chuang KV, Reisman SE. J. Am. Chem. Soc. 2013; 135: 5557

For reviews, see:

4a Mátyus P, Éliás O, Tapolcsányi P, Polonka-Bálint Á, Halász-Dajka B. Synthesis 2006; 2625
4b Peng B, Maulide N. Chem. Eur. J. 2013; 19: 13274
4c Wang L, Xiao J. Adv. Synth. Catal. 2014; 356: 1137
4d Haibach MC, Seidel D. Angew. Chem. Int. Ed. 2014; 53: 5010
4e Wang L, Xiao J. Top. Curr. Chem. 2016; 374: 17
4f Kwon SJ, Kim DY. Chem. Rec. 2016; 16: 1191
4g Xiao M, Zhu S, Shen Y.-B, Wang L, Xiao J. Chin. J. Org. Chem. 2018; 38: 328
4h An X.-D, Xiao J. Org. Chem. Front. 2021; 8: 1364

For representative examples, see:

4i Kaval N, Dehaen W, Mátyus P, Eycken EV. Green Chem. 2004; 6: 125
4j McQuaid KM, Sames D. J. Am. Chem. Soc. 2009; 131: 402
4k Cui L, Peng Y, Zhang L. J. Am. Chem. Soc. 2009; 131: 8394
4l Haibach MC, Deb I, De C K, Seidel D. J. Am. Chem. Soc. 2011; 133: 2100
4m Bolte B, Gagosz F. J. Am. Chem. Soc. 2011; 133: 7696
4n Chen D, Han Z, He Y, Yu J, Gong L. Angew. Chem. Int. Ed. 2012; 51: 12307
4o Bhunia S, Ghorpade S, Huple DB, Liu R. Angew. Chem. Int. Ed. 2012; 51: 2939
4p Jiao Z, Zhang S, He C, Tu Y, Wang S, Zhang F, Zhang Y, Li H. Angew. Chem. Int. Ed. 2012; 51: 8811
4q Suh CW, Kwon SJ, Kim DY. Org. Lett. 2017; 19: 1334
4r Ramakumar K, Maji T, Partridge JJ, Tunge JA. Org. Lett. 2017; 19: 4014
4s Yoshida T, Mori K. Chem. Commun. 2017; 53: 4319
4t Mori K, Isogai R, Kamei Y, Yamanaka M, Akiyama T. J. Am. Chem. Soc. 2018; 140: 6203
4u Jurberg ID, Peng B, Woestefeld E, Wasserloos M, Maulide N. Angew. Chem. Int. Ed. 2012; 51: 1950
4v Yokoo K, Mori K. Org. Lett. 2020; 22: 244
4w Mori K, Umeharaa N, Akiyama T. Chem. Sci. 2018; 9: 7327
4x Mori K, Kurihara K, Yabe S, Yamanaka M, Akiyama T. J. Am. Chem. Soc. 2014; 136: 3744

For selected examples, see:

5a Kang YK, Kim SM, Kim DY. J. Am. Chem. Soc. 2010; 132: 11847
5b Mori K, Ehara K, Kurihara K, Akiyama T. J. Am. Chem. Soc. 2011; 133: 6166
5c Mori K, Sueoka S, Akiyama T. J. Am. Chem. Soc. 2011; 133: 2424
5d Zhou G, Liu F, Zhang J. Chem. Eur. J. 2011; 17: 3101
5e Cao W, Liu X, Wang W, Lin L, Feng X. Org. Lett. 2011; 13: 600
5f Chen L, Zhang L, Lv J, Cheng J, Luo S. Chem. Eur. J. 2012; 18: 8891

For selected examples, see:

6a Zhang L, Chen L, Lv J, Cheng J.-P, Luo S. Chem. Asian J. 2012; 7: 2569
6b Alajarin M, Bonillo B, Marin-Luna M, Sanchez-Andrada P, Vidal A. Chem. Eur. J. 2013; 47: 16093
6c Murarka S, Deb I, Zhang C, Seidel D. J. Am. Chem. Soc. 2009; 131: 13226
6d Liu S, Qu J, Wang B. Chem. Commun. 2018; 54: 7928
6e Liu S, Zhang W, Qu J, Wang B. Org. Chem. Front. 2018; 5: 3008

7a Zhu S, Chen C, Xiao M, Yu L, Wang L, Xiao J. Green Chem. 2017; 19: 5653
7b Li S.-S, Lv X, Ren D, Shao C.-L, Liu Q, Xiao J. Chem. Sci. 2018; 9: 8253
7c Li S.-S, Zhou L, Wang L, Zhao H, Yu L, Xiao J. Org. Lett. 2018; 20: 138
7d Wang S, An X.-D, Li S.-S, Liu X, Liu Q, Xiao J. Chem. Commun. 2018; 54: 13833
7e Li S.-S, Zhu S, Chen C, Duan K, Liu Q, Xiao J. Org. Lett. 2019; 21: 1058
7f Lv X, Hu F, Duan K, Li S.-S, Liu Q, Xiao J. J. Org. Chem. 2019; 84: 1833
7g Zhu S, Chen C, Duan K, Sun Y.-M, Li S.-S, Liu Q, Xiao J. J. Org. Chem. 2019; 84: 8440
7h An XD, Duan K, Li X.-J, Yang J.-M, Lu Y.-N, Liu Q, Xiao J. J. Org. Chem. 2019; 84: 11839
7i Shen Y.-B, Li L.-F, Xiao M.-Y, Yang J.-M, Liu Q, Xiao J. J. Org. Chem. 2019; 84: 13935
7j Zhou L, Shen Y.-B, An X.-D, Li X.-J, Li S.-S, Liu Q, Xiao J. Org. Lett. 2019; 21: 8543
7k Wang S, Shen Y.-B, Li L.-F, Qiu B, Yu L, Liu Q, Xiao J. Org. Lett. 2019; 21: 8904
7l Shen Y.-B, Wang L.-X, Sun Y.-M, Dong F.-Y, Yu L, Liu Q, Xiao J. J. Org. Chem. 2020; 85: 1915
7m Duan K, Shi H, Wang L.-X, Li S.-S, Xu L, Xiao J. Org. Chem. Front. 2020; 7: 2511
7n Duan K, An X.-D, Li L.-F, Sun L.-L, Qiu B, Li X.-J, Xiao J. Org. Lett. 2020; 22: 2537
7o Zhou L, An X.-D, Yang S, Li X.-J, Shao C.-L, Liu Q, Xiao J. Org. Lett. 2020; 22: 776

8 Jessop PG. Green Chem. 2011; 13: 1391
9 Vadola PA, Carrera I, Sames D. J. Org. Chem. 2012; 77: 6689

10a Trost BM, Schroeder GM. J. Org. Chem. 2000; 65: 1569
10b Renard A, Lhomme J, Kotera M. J. Org. Chem. 2002; 67: 1302
10c Best D, Burns DJ, Lam HW. Angew. Chem. Int. Ed. 2015; 54: 7410

11 Zhao T, Zhang H, Cui L, Wang C, Qu J, Wang B. ChemistrySelect 2016; 1: 3713

12a Mori K, Sueoka S, Akiyama T. Chem. Lett. 2011; 40: 1386
12b Wang L, Xiao J. Org. Chem. Front. 2016; 3: 635

13a Bella M, Kobbelgaard S, Jørgensen KA. J. Am. Chem. Soc. 2005; 127: 3670
13b Kobbelgaard S, Bella M, Jørgensen KA. J. Org. Chem. 2006; 71: 4980
13c Kumar A, Yadav A, Verma A, Jana S, Sattar M, Kumar S, Prasad CD, Kumar S. Chem. Commun. 2014; 50: 9481

14a Miller AA. Antimicrob. Agents Chemother. 2008; 52: 2806
14b Barbachyn MR, Bundy GL, Dobrowolski PJ, Hurd AR, Martin GE, McNamara DJ, Palmer JR, Romero DL, Romero AG, Ruble JC, Sherry DA, Thomasco LM, Toogood PL. US Patent 7,208,490, 2003

Zusatzmaterial

Supporting Information