Synthesis of (2-Aminophenyl)(naphthalen-2-yl)methanones via Intramolecular Rearrangement of (E)-3-Styrylquinolin-4(1H)-ones under Irradiation with 365 nm UV Light

Sisi Jing; Yun He; Tao Wang; Jin Zhang; Anqi Cheng; Yong Liang; Zunting Zhang

doi:10.1055/s-0037-1610176

Synlett, Table of Contents

Synlett 2018; 29(12): 1578-1582
DOI: 10.1055/s-0037-1610176

letter

Synthesis of (2-Aminophenyl)(naphthalen-2-yl)methanones via Intramolecular Rearrangement of (E)-3-Styrylquinolin-4(1H)-ones under Irradiation with 365 nm UV Light

Sisi Jing

,

Yun He

,

Tao Wang

,

Jin Zhang

,

Anqi Cheng

,

Yong Liang

,

Zunting Zhang*

Abstract

All articles of this category

Abstract

A highly efficient and environmentally friendly synthesis of (2-aminophenyl)(naphthalen-2-yl)methanones was developed. The (2-aminophenyl)(naphthalen-2-yl)methanone derivatives were obtained in high yields (up to 96%) by the irradiation of (E)-3-styrylquinolin-4(1H)-ones in EtOH–H₂O (7:1) with UV light (365 nm) at room temperature under Ar atmosphere. The demonstrated photoinduced intramolecular rearrangement has advantages over other transition-metal-catalyzed reactions, e.g. no requirement of additives, green solvent, broad substrate scope, and high atom efficiency.

Key words

(2-aminophenyl)(naphthalen-2-yl)methanones - (E)-3-styrylquinolin-4(1H)-ones - photo rearrangement reaction - photochemical reaction - synthesis

Full Text

References

References and Notes
1 Present Address: Department of Molecular Medicine, Beckman Research Institute of City of Hope Duarte, CA 91010, USA.
2 Liou JP. Chang CW. Song JS. Yang YN. Yeh CF. Tseng HY. Lo YK. Chang YL. Chang CM. Hsieh HP. J. Med. Chem. 2002; 45: 2556
3 Singh RK. Prasad DN. Bhardwaj TR. Med. Chem. Res. 2013; 22: 5901
4 Welstead WJ. Moran HW. Stauffer HF. Turnbull LB. Sancilio LF. J. Med. Chem. 1979; 22: 1074
5 Maleki B. Seresht ER. Ebrahimi Z. Org. Prep. Proced. Int. 2015; 47: 149
6 Cai S. Zeng J. Bai Y. Liu XW. J. Org. Chem. 2012; 77: 801
7 Yan Y. Wang Z. Chem. Commun. 2011; 47: 9513
8 Yan Y. Shi M. Niu B. Meng X. Zhu C. Liu G. Chen T. Liu Y. RSC Adv. 2016; 6: 36192
9 Castellano S. Taliani S. Viviano M. Milite C. Da PE. Costa B. Barresi E. Bruno A. Cosconati S. Marinelli L. Greco G. Novellino E. Sbardella G. Da SF. Martini C. J. Med. Chem. 2014; 57: 2413
10 Jung DI. Song JH. Lee EJ. Kim YY. Lee DH. Lee YG. Hahn JT. Tetrahedron Lett. 2009; 50: 5805
11 Earmme T. Ahmed E. Jenekhe SA. Adv. Mater. 2010; 22: 4744
12 Chen J. Ye L. Su W. Biomol. Chem. 2014; 12: 8204
13 Chen J. Li J. Su W. Molecules 2014; 19: 6439
14 Aidene M. Belkessam F. Soulé JF. Doucet H. ChemCatChem 2016; 8: 1583
15 Luo S. Hu Z. Zhu Q. Org. Chem. Front. 2016; 3: 364
16 Gaslonde T. Covello F. Velazquez-Alonso L. Léonce S. Pierré A. Pfeiffer B. Michel S. Tillequin F. Eur. J. Med. Chem. 2011; 46: 1861
17 Hook BD. A. Dohle W. Hirst PR. Pickworth M. Berry MB. Booker-Milburn KI. J. Org. Chem. 2005; 70: 7558
18 Roth HD. Angew. Chem. Int. Ed. Engl. 1989; 28: 1193
19 Oelgemöller M. Chem. Rev. 2016; 116: 9664
20 Zhang J. Zhang X. Wang T. Yao X. Wang P. Wang P. Jing S. Liang Y. Zhang Z. J. Org. Chem. 2017; 82: 12097
21 Han J. Wang T. Liang Y. Li Y. Li C. Wang R. Feng S. Zhang Z. Org. Lett. 2017; 19: 3552
22 Kang Y. Wang T. Liang Y. Zhang Y. Wang R. Zhang Z. RSC Adv. 2017; 7: 44333
23 Yang Q. Wang R. Han J. Li C. Wang T. Liang Y. Zhang Z. RSC Adv. 2017; 7: 43206
24 Wei W. Li C. Wang T. Liu D. Zhang Z. Tetrahedron 2016; 72: 5037
25 Xue P. Du Z. Wang T. Zhang Z. Synthesis 2015; 47: 3385
26 Wang Q. Zhang Z. Du Z. Hua H. Chen S. Green Chem. 2013; 15: 1048
27 Fan J. Wang T. Li C. Wang R. Lei X. Liang Y. Zhang Z. Org. Lett. 2017; 19: 5984
28 Seixas RS. G. R. Silva AM. S. Alkorta I. Elguero J. Monatsh. Chem. 2011; 142: 731
29 Seixas RS. G. R. Silva AM. S. Cavaleiro JA. S. Synlett 2010; 15: 2257
30 Seubert CK. Sun Y. Thiel WR. Dalton Trans. 2009; 38: 4971
31 Ho JH. Lee YW. Chen YZ. Chen PS. Liu WQ. Ding YS. Tetrahedron 2013; 69: 7325
32 General Procedure for the Synthesis of (2-Aminophenyl)(naphthalen-2-yl)methanones (2a–2u): (E)-3-styrylquinolin-4(1H)-ones 1 (0.20 mmol, 5 mM) was dissolved or suspended in EtOH–H₂O (7:1, 40 mL) in four quartz tubes (4 × 10 mL). The solution/suspension was bubbled with argon (3 × 2 min) and sealed. The resulting mixture was irradiated with a UV lamp (365 nm, 10 W) at r.t. for 9.0 h (1a–1k, 1t, 1u) or 4.5 h (1l–1s). The reaction mixture in four quartz tubes was combined and volatiles were removed under reduced pressure. The oily residue was column chromatographed (petroleum ether/EtOAc = 20:1) to give (2-aminophenyl)(naphthalen-2-yl)methanones 2.
33 Irie M. Fukaminato T. Matsuda K. Kobatake S. Chem. Rev. 2014; 114: 12174
34 Ho TI. Wu JY. Wang SL. Angew. Chem. Int. Ed. 1999; 38: 2558
35 Ho TI. Ho JH. Wu JY. J. Am. Chem. Soc. 2000; 122: 8575
36 Samori S. Hara M. Ho TI. Tojo S. Kawai K. Endo M. Fujitsuka M. Majima T. J. Org. Chem. 2005; 70: 2708
37 Lvov AG. Shirinyan VZ. Chem. Heterocycl. Compd. 2016; 52: 658
38 Lvov AG. Shirinian VZ. Zakharov AV. Krayushkin MM. Kachala VV. Zavarzin IV. J. Org. Chem. 2015; 80: 11491

Supplementary Material

Supporting Information