Photoredox One-Pot Synthesis of 3,4-Dihydroquinolin-2(1H)-ones

Jing-Yao He; Qi-Fan Bai; Xuewen Li; Jianxin Shou; Gaofeng Feng

doi:10.1055/s-0041-1737910

Synlett, Table of Contents

Synlett 2022; 33(07): 679-683
DOI: 10.1055/s-0041-1737910

letter

Photoredox One-Pot Synthesis of 3,4-Dihydroquinolin-2(1H)-ones

Jing-Yao He

^aZhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. of China

,

Qi-Fan Bai

^aZhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. of China

,

Xuewen Li

^aZhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. of China

,

Jianxin Shou∗

^bOffice of Science and Technology, Shaoxing University, Shaoxing 312000, P. R. of China

,

Gaofeng Feng∗

^aZhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. of China

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Abstract

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Abstract

A photoredox one-pot strategy for efficient accessing 3,4-dihydroquinolin-2(1H)-ones from anilines, oxalyl chloride, and electron-deficient alkenes is disclosed. The new approach features excellent synthetic efficiency, readily available starting materials, and simple operations. It is compatible with a variety of anilines and electron-deficient alkenes. A broad array of 3,4-dihydroquinolin-2(1H)-ones were prepared.

Key words

3,4-dihydroquinolin-2(1H)-one - photoredox catalysis - one-pot synthesis - efficient synthesis - oxalyl chloride

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References

References and Notes

1a McCoull W, Abrams RD, Anderson AE. Blades K, Barton P, Box M, Burgess J, Byth K, Cao Q, Chuaqui C, Carbajo RJ, Cheung T, Code E, Ferguson AD, Fillery S, Fuller NO, Gangl E, Gao N, Grist M, Hargreaves D, Howard MR, Hu J, Kemmitt PD, Nelson JE, O’Connell N, Prince DB, Raubo P, Rawlins PB, Robb GR, Shi J, Waring MJ, Whittaker D, Wylot M, Zhu X. J. Med. Chem. 2017; 60: 4386
1b An C.-Y, Li X.-M, Luo H, Li C.-S, Wang M.-H, Xu G.-M, Wang B.-G. J. Nat. Prod. 2013; 76: 1896
1c Uchida R, Imasato R, Yamaguchi Y, Masuma R, Shiomi K, Tomoda H, Omura S. J. Antibiot. 2006; 59: 646
1d He J, Lion U, Sattler I, Gollmick FA, Grabley S, Cai J, Meiners M, Schuenke H, Schaumann K, Dechert U, Krohn M. J. Nat. Prod. 2005; 68: 1397

2 Dounay AB, Anderson M, Beche BM, Campbell BM, Claffey MM, Evdokimov A, Evrard E, Fonseca KR, Gan X, Ghosh S, Hayward MM, Horner W, Kim J.-Y, McAllister LA, Pandit J, Paradis V, Parikh VD, Reese MR, Rong S, Salafia MA, Schuyten K, Strick CA, Tuttle JB, Valentine J, Wang H, Zawadzke LE, Verhoest PR. ACS Med. Chem. Lett. 2012; 3: 187
3 Bello FD, Bonifazi A, Giorgioni G, Cifani C, Bonaventura MV. M. D, Petrelli R, Piergentili A, Fontana S, Mannoli V, Yano H, Matucci R, Vistoli G, Quaglia W. J. Med. Chem. 2018; 61: 3712
4 Saku O, Ishida H, Atsumi E, Sugimoto Y, Kodaira H, Kato Y, Shirakura S, Nakasato Y. J. Med. Chem. 2012; 55: 3436
5 A review for 3,4-dioxygenated 5-hydroxy-4-aryl-quinolin-3(1H)-one alkaloids: Simonetti SO, Larghi EL, Kaufman TS. Nat. Prod. Rep. 2016; 33: 1425
6 Chen M, Shao C.-L, Meng H, She Z.-G, Wang C.-Y. J. Nat. Prod. 2014; 77: 2720

For selected examples, see:

7a Disadee W, Lekky A, Ruchirawat S. J. Org. Chem. 2020; 85: 1802
7b Xiong W, Hu K, Lei Y, Zhen Q, Zhao Z, Shao Y, Li R, Zhang Y, Chen J. Org. Lett. 2020; 22: 1239
7c Jiang B, Tu S.-J, Kaur P, Wever W, Li G. J. Am. Chem. Soc. 2009; 131: 11660
7d Hummel JR, Boerth JA, Ellman JA. Chem. Rev. 2017; 117: 9163

For examples of domino reactions, see:

8a Zhang X.-J, Wang Z, Zhang H, Gao J.-J, Yang K.-R, Fan W.-Y, Feng M.-L, Zhu W, Zhu Y.-P. J. Org. Chem. 2022; 87: 835
8b Zhang P, Guo Y, Luan X. J. Am. Chem. Soc. 2021; 143: 21270
8c Xiao F, Yuan S, Huang H, Zhang F, Deng G.-J. Org. Lett. 2019; 21: 8533
8d Mupparapu N, Khan S, Bandhoria P, Athimoolam S, Ahmed QN. ACS Omega 2018; 3: 5445
8e Volla CM. R, Atodiresei I, Rueping M. Chem. Rev. 2014; 114: 2390
8f Tietze L. Chem. Rev. 1996; 96: 115

For selected example, see:

9a Zhang W.-B, Chen G, Shi S.-L. J. Am. Chem. Soc. 2022; 144: 130
9b Chen W, Li Z. J. Org. Chem. 2022; 87: 76
9c Kang Z, Chang W, Tian X, Fu X, Zhao W, Xu X, Liang Y, Hu W. J. Am. Chem. Soc. 2021; 143: 20818
9d Reguera L, Rivera DG. Chem. Rev. 2019; 119: 9836
9e Zeng L, Sajiki H, Cui S. Org. Lett. 2019; 21: 5269
9f Neochoritis CG, Zhao T, Dömling A. Chem. Rev. 2019; 119: 1970
9g Allais C, Grassot J.-M, Rodriguez J, Constantieux T. Chem. Rev. 2014; 114: 10829

Selected examples for synthesis of 3,4-dihydroquinolin-2(1H)-ones, see:

10a Sun W, Ling C.-H, Au C.-M, Yu W.-Y. Org. Lett. 2021; 23: 3310
10b Du J, Wang X, Wang H, Wei J, Huang X, Song J, Zhang J. Org. Lett. 2021; 23: 5631
10c Wang S.-W, Yu J, Zhou Q.-Y, Chen S.-Y, Xu Z.-H, Tang S. ACS Sustainable Chem. Eng. 2019; 7: 10154
10d Yang Z, Jiang K, Chen Y.-C, Wei Y. J. Org. Chem. 2019; 84: 6 3725
10e Xiao H.-Z, Wang W.-S, Sun Y.-S, Luo H, Li B.-W, Wang X.-D, Lin W.-L, Luo F.-X. Org. Lett. 2019; 21: 1668
10f Wang K, Chen X, Yuan M, Yao M, Zhu H, Xue Y, Luo Z, Zhang Y. J. Org. Chem. 2018; 83: 1525
10g Cui Z, Du D.-M. J. Org. Chem. 2018; 83: 5149
10h Faggyas R, Grace M, Williams L, Sutherland A. J. Org. Chem. 2018; 83: 12595
10i Petersen WF, Taylor RJ. K, Donald JR. Org. Biomol. Chem. 2017; 15: 5831
10j Petersen WF, Taylor RJ. K, Donald JR. Org. Lett. 2017; 19: 874
10k Guan M, Pang Y, Zhang J, Zhao Y. Chem. Commun. 2016; 52: 7043
10l Torisawa Y, Nishi T, Minamikawa J. J. Bioorg. Med. Chem. Lett. 2007; 17: 448
10m Yan J.-X, Li H, Liu X.-W, Shi J.-L, Wang X, Shi Z.-J. Angew. Chem. Int. Ed. 2014; 53: 4945
10n Deng Y, Gong W, He J, Yu J.-Q. Angew. Chem. Int. Ed. 2014; 53: 6692
10o Tian J, Li L, Yan X.-L, Chen L.-G. J. Heterocycl. Chem. 2014; 51: 1811
10p Wasa M, Yu J.-Q. J. Am. Chem. Soc. 2008; 130: 14058
10q Shi Z.-Z, Boultadakis-Arapinis M, Glorius F. Chem. Commun. 2013; 49: 6489
10r Wang C.-M, Chen H, Wang Z.-F, Chen J.-A, Huang Y. Angew. Chem. Int. Ed. 2012; 51: 7242
10s Tsuritani T, Yamamoto Y, Kawasaki M, Mase T. Org. Lett. 2009; 5: 1043
10t Jia J, Sarker M, Steinmetz MG, Shukla R, Rathore R. J. Org. Chem. 2008; 73: 8867

11 Bei Q.-F, Jin C, He J.-Y, Feng G. Org. Lett. 2018; 20: 2172
12 General Procedure for Photoredox One-Pot Synthesis of 3,4-Dihydroquinolin-2(1H)-ones 8a–t To a dry 20 mL reaction vial equipped with a stir bar was charged with CH₂Cl₂ (2 mL) and oxalyl chloride (3 mmol, 10 equiv), then a solution of anilines (0.3 mmol, 1.0 equiv) in CH₂Cl₂ (2 mL) was added quickly at room temperature. After stirring at the same temperature for 1 h, H₂O (2 mL) was added to the mixture, followed by Ir[dF(CF₃)ppy]₂(dtbbpy)PF₆ (2 mol%), K₂CO₃ (1.5 mmol, 5 equiv), and alkenes (0.9 mmol, 3.0 equiv). The vial was covered and bubbled with nitrogen for 5 min. After irradiated with 36 W blue LEDs for 36 h, the mixture was then diluted with EtOAc (40 mL) and H₂O (5 mL), and the organic layer was recovered, washed with brine, dried over Na₂SO₄, filtrated, concentrated under reduced pressure, and purified with column chromatography to afford 3,4-dihydroquinolin-2(1H)-ones 8a–t.
13 1-Benzyl-6-methyl-4-(phenylsulfonyl)-3,4-dihydroquinolin-2(1H)-one (8o) Pale yellow solid; yield 38% (44.7 mg); R_f = 0.14 (25% EtOAc–PE); mp 161–163 °C. IR (film): 2929, 1673, 1509, 1447, 1377, 1308, 1265, 1147, 815 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 7.70–7.64 (m, 3 H), 7.53–7.49 (m, 2 H), 7.32–7.28 (m, 2 H), 7.25–7.22 (m, 1 H), 7.17–7.13 (m, 3 H), 7.05 (dd, J = 8.4, 1.6 Hz, 1 H), 6.63 (d, J = 8.4 Hz, 1 H), 5.10 (d, J = 16.4 Hz, 1 H), 4.36 (d, J = 7.2 Hz, 1 H), 4.02 (d, J = 16.0 Hz, 1 H), 3.48 (d, J = 17.6 Hz, 1 H), 3.19 (dd, J = 17.6, 7.6 Hz, 1 H), 2.30 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 165.3, 138.2, 136.4, 136.0, 134.2, 132.9, 132.2, 131.2, 129.6 (2×), 128.8 (2×), 128.7 (2×), 127.1, 126.1 (2×), 115.9, 115.7, 63.1, 46.5, 31.9, 20.4. GC–MS: m/z (%) = 91 (100), 249 (95) [M – HSO₂Ph]⁺. HRMS (ESI⁺): m/z [M + H]⁺ calcd for C₂₃H₂₂NO₃S: 392.1315; found: 392.1316.
14 1-Benzyl-6-methyl-4-propionyl-3,4-dihydroquinolin-2(1H)-one (8p) Pale yellow solid; yield 52% (48.1 mg). R_f = 0.17 (25% EtOAc–PE), mp 118–120 °C. IR (film): 2924, 2854, 1711, 1672, 1505, 1375, 1095, 1030, 803 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 7.31–7.28 (m, 4 H), 7.24–7.19 (m, 3 H), 7.10 (d, J = 1.6 Hz, 1 H), 6.97 (dd, J = 8.4, 1.2 Hz, 1 H), 6.81 (d, J = 8.4 Hz, 1 H), 5.21 and 5.11 (AB q, J = 16.4, 16.0 Hz, 2 H), 3.85 (dd, J = 6.0, 2.8 Hz, 1 H), 3.16 (dd, J = 16.0, 2.8 Hz, 1 H), 2.84 (dd, J = 16.0, 6.0 Hz, 1 H), 2.55–2.49 (m, 2 H), 2.31 (s, 3 H), 1.01 (t, J = 7.2 Hz, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 208.2, 168.8, 137.0, 136.9, 132.8, 129.5, 129.2, 128.6 (2×), 127.0, 126.7 (2×), 123.1, 116.2, 49.1, 45.5, 33.4, 33.3, 20.5, 7.6. GC–MS: m/z (%) = 91 (100), 307 (22) [M]⁺. HRMS (ESI⁺): m/z [M + H]⁺ calcd for C₂₀H₂₂NO₂: 308.1645; found: 308.1645.

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