Synlett 2021; 32(10): 987-992
DOI: 10.1055/a-1468-6231
letter

Visible-Light-Mediated Synthesis of Rutaecarpine Alkaloids through C–N Cross-Coupling Reaction

Dong Chen
a   College of Chemistry and Bioengineering, Guangxi Key Laboratory of Electrochemical and Magnetochemical Functional Materials, Guilin University of Technology, 12 Jian Gan Road, Guilin 541004, P. R. of China
,
Shiqing Li
a   College of Chemistry and Bioengineering, Guangxi Key Laboratory of Electrochemical and Magnetochemical Functional Materials, Guilin University of Technology, 12 Jian Gan Road, Guilin 541004, P. R. of China
,
Jinhua Wang
b   State Key laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin, 541004, P. R. of China
,
Tiantian Gou
a   College of Chemistry and Bioengineering, Guangxi Key Laboratory of Electrochemical and Magnetochemical Functional Materials, Guilin University of Technology, 12 Jian Gan Road, Guilin 541004, P. R. of China
,
Linfeng Zhang
a   College of Chemistry and Bioengineering, Guangxi Key Laboratory of Electrochemical and Magnetochemical Functional Materials, Guilin University of Technology, 12 Jian Gan Road, Guilin 541004, P. R. of China
,
Guixia Wang
a   College of Chemistry and Bioengineering, Guangxi Key Laboratory of Electrochemical and Magnetochemical Functional Materials, Guilin University of Technology, 12 Jian Gan Road, Guilin 541004, P. R. of China
,
Xiangfei Kong
a   College of Chemistry and Bioengineering, Guangxi Key Laboratory of Electrochemical and Magnetochemical Functional Materials, Guilin University of Technology, 12 Jian Gan Road, Guilin 541004, P. R. of China
› Author Affiliations
This work was supported by the Natural Science Foundation of Guangxi Province (2020GXNSFAA297251), the National Natural Science Foundation of China (22001049) and the Key Laboratory of Electrochemical and Magnetochemical Function Materials.


Abstract

A visible-light-initiated cross-dehydrogenative-coupling amination is described, featuring metal- and photocatalyst-free, at room temperature, and using air as an oxidant. The reaction provides a facile approach for the synthesis of rutaecarpine and its derivatives. The substrates with electron-withdrawing groups give higher yields than those with electron-donating groups, but the substituent position has a negligible influence on the yield. Using binaphthyl-diyl hydrogen phosphate and dibenzyl phosphate as catalysts both deliver satisfying yields. This straightforward light-driven strategy might be applicable to the synthesis of quinazolinone derivatives.

Supporting Information



Publication History

Received: 28 February 2021

Accepted after revision: 27 March 2021

Accepted Manuscript online:
27 March 2021

Article published online:
13 April 2021

© 2021. Thieme. All rights reserved

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  • 26 Mass spectra were obtained by using a LCMS-9030 quadrupole mass spectrometer (SHIMADZU, Japan) equipped with an APCI source operated in positive/negative ion mode and an Agilent SB C18 column (150 mm × 2.1 mm, I.D., particle size 5 μm) with ultraviolet detection at 344 nm. The mobile phase was acetonitrile–water (51:49, v/v) at a flow rate of 0.2 mL/min at room temperature.
  • 27 Typical Procedures A glass tube (10 mL) was charged with 2a (0.022 g, 0.075 mmol), (R)-BPA (0.0025 g, 0.0075 mmol), and 1,4-dioxane (0.5 mL), then closed under air. The reaction was put on the photoreactor which is cooled by 25 °C water, irradiated for 12 h. After the reaction was completed (monitored by TLC), the solvent was removed under reduced pressure, and the crude product was purified by flash chromatography to give 1a in 70% yield; mp 259–261 °C. 1H NMR (500 MHz, CDCl3): δ = 9.51 (s, 1 H), 8.33–8.31 (m, 1 H), 7.70 (t, J = 7.5 Hz, 1 H), 7.66–7.61 (m, 2 H), 7.42 (t, J = 7.5 Hz, 1 H), 7.36 (d, J = 5.0 Hz, 1 H), 7.31 (t, J = 7.5 Hz, 1 H), 7.17 (t, J = 7.5 Hz, 1 H), 4.59 (t, J = 5.0 Hz, 2 H), 3.23 (t, J = 5.0 Hz, 2 H). 13C NMR (126 MHz, CDCl3): δ = 161.62, 147.50, 145.03, 138.31, 134.36, 127.26, 127.18, 126.60, 126.23, 125.64, 125.59, 121.18, 120.63, 120.10, 118.39, 112.10, 41.14, 19.68. According to the procedures reported previously, 2a was readily prepared form 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]-indole (3) and 2-aminobenzoic acid in the presence of HATU and Et3N,23 and tryptamine reacted with paraformaldehyde in the mixed solvent of acetic acid and methanol to give 3.28
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