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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
a   Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. of China
,
Qi-Fan Bai
a   Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. of China
,
Xuewen Li
a   Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. of China
,
Jianxin Shou∗
b   Office of Science and Technology, Shaoxing University, Shaoxing 312000, P. R. of China
,
Gaofeng Feng∗
a   Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. of China
› Author AffiliationsFinancial supports by National Natural Science Foundation of China (NO 21302130 and 21676166) and Science Technology Department of Zhejiang Province (2014C31141 and LGG20B060002) are acknowledged with thanks.
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737910.
  • Supporting Information


Publication History

Received: 22 January 2022

Accepted after revision: 16 February 2022

Article published online:
08 March 2022

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  • 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); Rf = 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). Rf = 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.