催化学报  2014, Vol. 35 Issue (11): 1840-1845   PDF (504 KB)    
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张亦猛
张涛
詹豪强
李兴伟
Rh(Ⅲ)-catalyzed synthesis of (dihydro)quinolines via the annulation of N-sulfonyl 2-aminobenzaldehydes with olefins
YimengZhanga,b, Tao Zhangb,c, HaoqiangZhana , XingweiLib     
a Chemical Synthesis and pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637009, Sichuan, China;
b Dalian Institute of Chemical Physics, Chinese Academy of Science, Dalian 116023, Liaoning, China;
c College of Chemistry and Materials Science, South-Central University for Nationalities, Wuhan 430074, Hubei, China
Received: 2014-4-28. Accepted: 2014-5-23. Published: 2014-11-20.
* Corresponding author. Tel:+86-411-84379089;E-mail:xwli@dicp.ac.cn
#Corresponding author. Tel:+86-15881716179;E-mail:1276554568@qq.com
Foundation Item:This work was supported by the National Natural Science Foundation of China (21272231).
Abstract: We developed a new synthetic method for the production of 1,2-dihydroquinolines and quinolines via the Rh(Ⅲ)-catalyzed annulation of N-sulfonyl 2-aminobenzaldehydes with olefins. Various functionalities were found to be compatible under the operationally simple conditions. This study provides the first example of a Rh(Ⅲ)-catalyzed synthesis of 1,2-dihydroquinolines.
© 2014, Dalian Institute of Chemical Physics, Chinese Academy of Sciences.
Published by Elsevier B.V. All rights reserved.
Key words: Rhodium(Ⅲ)     N-sulfonyl 2-aminobenzaldehyde     Olefin     Quinoline    
铑(Ⅲ)催化N-磺酰基2-甲酰苯胺与烯烃环化制备(2H)喹啉
张亦猛a,b, 张涛b,c, 詹豪强a , 李兴伟b     
a 西华师范大学化学化工学院, 四川省化学合成与污染控制重点实验室, 四川南充637009;
b 中国科学院大连化学物理研究所, 辽宁大连116023;
c 中南民族大学化学与材料学院, 湖北武汉430074
收稿日期: 2014-4-28. 接受日期: 2014-5-23. 出版日期: 2014-11-20.
基金来源：国家自然科学基金(21272231).
*通讯联系人.詹豪强,电话: (0411)84379089; 电子信箱: xwli@dicp.ac.cn,李兴伟,电话: 15881716179; 电子信箱: 1276554568@qq.com
摘要：开发了一种用铑(Ⅲ)催化的N-磺酰基2-氨基苯甲醛与烯烃环化生成喹啉衍生物的方法, 得到较高产率的喹啉衍生物, 并且在反应条件下, 反应具有较好的官能团兼容性. 这是首次运用铑(Ⅲ)作为催化剂合成烷基1-磺酰基-1,2-二氢喹啉-3-羧酸酯. 该催化体系表现较好的催化性且反应操作较为简单.
关键词： 三价铑     氮-磺酰基2-氨基苯甲醛     烯烃     喹啉衍生物    

1. Introduction

Quinolines are an important structural motif for a wide range of biologically active natural products and they have important physiological activity [1, 2]. The most popular methods of quinoline synthesis include the Skraup quinoline synthesis, the Fridländer quinoline synthesis, the Camps quinoline synthesis, the Combes quinoline synthesis, and the Doebner quinoline syhthesis, among others [3]. These synthetic procedures usually require harsh conditions and they generate a large amount of byproducts. Other novel and effective strategies have recently been to developed for the synthesis of these compounds [4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57]. In particular, transition metals such as In [26, 27], Ga [27], Pt [27, 28], Pd [30, 31, 32, 33, 34, 35, 36, 37], Rh [36, 37, 38, 39, 40, 41, 42, 43, 44], Ru [45, 46, 47, 48, 49, 50, 51, 52, 53], Fe [54], Ni [55], Cu [56] and Au [57] have been used as active catalysts to effect the formation of quinolines. Rh catalysts have become an increasing important tool for the construction of complex organic molecules [58, 59]. New strategies have been developed for synthesis of dihydroquinolines such as the use of 1-tosyl-1,2-dihydroquinoline-3-carboxylate [18, 31, 56]. However the preparation of the starting materials is often tedious and a long reaction time is frequently requires (Scheme 1). It is thus desirable to develop more efficient methods for the formation of dihydroquinoline and quinolines.

Scheme 1. Quinoline derivate synthesis by the annulation of olefins.

We have previously demonstrated that N-sulfonyl 2-amino benzaldehydes coupled with various activated and unactivated olefins under redox-neutral conditions give hydroacylation product via a C-H activation pathway [60]. We then focused on the identification of a suitable catalyst and reaction conditions for the selective cyclization of activated olefins with N-sulfonyl-2-aminobenzaldehydes. To our delight, we discovered a very efficient method to synthesize 1-tosyl-1,2- dihydroquinoline-3-carboxylate (3a). Herein, we report the synthesis of such (dihydro)quinoline derivatives via the efficient coupling of activated alkenes with N-sulfonyl-2- aminobenzaldehydes (Scheme 1(4)).

2. Experimental
2.1. General remarks

All the olefins were obtained from commercial sources and were used as received unless otherwise noted. The symmetrical N-sulfonyl 2-aminobenzaldehydes were synthesized according to reported procedures [30, 61]. All reactions were carried out using Schlenk techniques or in an Ar-filled glovebox. Column chromatography was performed on silica gel (300-400 mesh) using ethyl acetate (EA)/petroleum ether (PE) or dichloromethane (DCM).

NMR Spectra were recorded on a Bruker 400 MHz or 500 MHz NMR spectrometer in the NMR solvent indicated. The chemical shift is given in dimensionless δ values and is frequency referenced to TMS for 1H and 13C NMR spectroscopy. HRMS data were obtained on a Thermo Scientific LTQ Orbirap Discovery (Bremen, Germany).

2.2. General procedure for the annulative coupling between N-sulfonyl 2-aminobenzaldehydes and acrylates.

N-sulfonyl 2-aminobenzaldehyde (0.2 mmol), acrylate ester (0.8 mmol), [Cp*RhCl2]2 (2.5 mol%), Ag2CO3 (0.4 mmol), and K2CO3 (0.6 mmol) were charged into a pressure tube, and CH3CN (2 mL) was added under Ar. The reaction mixture was stirred at 110 °C for 18 h. After cooling to room temperature, the solvent was removed under reduced pressure and the residue was purified by silica gel chromatography using EA/PE to afford the cyclization product.

3. Results and discussion

We initially used N-sulfonyl-2-aminoben-zaldehyde (1a) and ethyl acrylate (2a) as coupling partners, [RhCp*Cl2]2 as the catalyst in the presence of Ag2CO3 (2 equiv) in MeCN. However, no desired product was observed (Table 1, entry 1). To our delight, the desired ethyl 1-tosyl-1,2-dihydroquinoline-3- carboxylate (3a) was obtain in 87% yield when K2CO3 was introduced (entry 2). Omission of RhIII completely shut down the reaction demonstrating its important role (entry 5). Two other catalysts, [RhCp*(MeCN)3](SbF6)2 and [Ru(p-cymene)Cl2]2, were also then examined but they gave essentially no activity (entries 3,4). When the reaction was conducted in the absence of Ag2CO3, a lower yield of the desired products was isolated (entry 6). The product yield reduced to 77% when one equiv of Ag2CO3 was used, and this showed that this base played a vital role in the reaction. Screening with other bases indicated that Ag2CO3 was the best base (entries 2,8,9). The effects of the solvent were also examined and CH3CN was confirmed to be the best solvent for the reaction (entries 10-12). An investigation into the effect of the reaction temperature revealed that when the reaction temperature was lowered from 110 °C to 100 °C, the total yield decreased slightly (entries 2,13), and 110°C is thus suggested.

Table 1
Optimization of the reaction conditions for coupling between N-sulfonyl-2-aminobenzaldehyde and ethyl acrylate a.

To determine the scope of this coupling system, the optimized reaction conditions were used for reactions between different N-sulfonyl-2-aminobenzaldehydes and olefins (Table 2). The results reveal that the optimized procedure tolerates a range of different 2-aminobenzaldehydes. With the introduction of electron-donating or -withdrawing groups, for example methyl (1b), fluoro (1c), chloro (1d), bromo (1f), and nitro (1j) at the meta and para positions of the phenyl ring of the 2-aminobenzaldehydes, the reactions proceeded smoothly, and the resulting coupling products were isolated in moderate to good yields. Notably, the tolerance of the halides (3f, 3g, and 3h) may offer further opportunity for subsequent derivatization. While N-(2-formyl-5-nitrophenyl)-4- methylbenzenesulfonamide (1g) also participated in this reaction, a quinoline product was isolated (3j), which is believed to be a result of the in situ elimination of a Ts-H molecule from the dihydroquinoline intermediate. The substrate scope was further extended to a wide variety of olefins, and electron-deficient olefins such as methyl acrylate (2b), butyl acrylate (2c), benzyl acrylate (2d), acrylonitrile (2e) and phenyl vinyl sulfone (2f) were suitable for this transformation. Surprisingly, we also obtained the corresponding quinoline products in moderate yields for acrylonitrile and phenyl vinyl sulfone (3k and 3l). These electron-withdrawing groups facilitate the 1,2-elimination of Ts-H. Given the prevalence of quinolines in natural products and in pharmaceuticals, this simple and convenient method for the synthesis of 1-tosyl-1,2-dihydroquinolines represents an attractive strategy.

Table 2
Annulation between N-sulfonyl 2-aminobenzaldehydes and olifins a.
4. Proposed mechanism

Although no solid evidence was obtained for the current coupling system, a tentative mechanism is proposed to explain the observed transformation (Scheme 2). In the presence of a base, deprotonation and coordination of the sulfonamide (Ⅰ) generate a RhⅢ amidate intermediate (Ⅱ). The subsequent coordination of the activated olefin and insertion of the Rh-N bond into the olefin (Michael-like addition) are followed by intramolecular Aldol condensation, which gives the dihydroquinoline product (Ⅳ). The stability of the dihydroquinoline (Ⅳ) is influenced by the effects of the base and the electron-withdrawing nature of the substituent. For example, acrylonitrile (3-position in Ⅳ), phenyl vinyl sulfone (3-position in Ⅳ), and nitro groups (7-position in Ⅳ) tend to favor in situ 1,2-elimination to give a quinoline.

Scheme 2. Proposed mechanism for the formation of quinoline derivates.
5. Experimental data for the products

Ethyl 1-tosyl-1,2-dihydroquinoline-3-carboxylate(3a). 87% yield. 1H NMR (400 MHz, CDCl3): δ = 7.76 (d, J = 8.1 Hz, 1H), 7.41 (t, J = 7.2 Hz, 1H), 7.27-7.24 (m, 3H), 7.12 (d, J = 6.9 Hz, 1H), 7.05 (d, J = 8.1 Hz, 2H), 6.96 (s, 1H), 4.67 (s, 2H), 4.22 (q, J = 7.1 Hz, 2H), 2.33 (s, 3H), 1.32 (t, J = 7.1 Hz, 3H).13C NMR (101 MHz, CDCl3): δ = 164.4, 144.0, 136.3, 136.0, 133.5, 130.6, 129.3, 128.7, 128.2, 127.4, 127.1, 127.0, 125.5, 61.0, 44.5, 21.7, 14.5. The NMR data agree with those in a literature report [56]. HRMS: [M + NH4]+ calculated for C19H23N2O4S: 375.13730, found 375.13840.

Methyl 1-tosyl-1,2-dihydroquinoline-3-carboxylate (3b). 91% yield. 1H NMR (500 MHz, CDCl3): δ = 7.76 (d, J = 8.1 Hz, 1H), 7.41 (td, J = 7.8, 1.6 Hz, 1H), 7.27-7.24 (m, 3H), 7.11 (dd, J = 7.6, 1.5 Hz, 1H), 7.05 (d, J = 8.0 Hz, 2H), 6.97 (s, 1H), 4.68 (d, J = 1.3 Hz, 2H), 3.77 (s, 3H), 2.33 (s, 3H). 13C NMR (126 MHz, CDCl3): δ = 164.9, 144.0, 136.4, 136.0, 133.8, 130.7, 129.3, 128.7, 128.1, 127.3, 127.2, 127.1, 125.2, 52.1, 44.5, 21.7. HRMS: [M + H]+ calculated for C18H18NO4S: 344.09511, found 344.09515.

Butyl 1-tosyl-1,2-dihydroquinoline-3-carboxylate (3c). 82% yield. 1H NMR (400 MHz, CDCl3): δ = 7.76 (d, J = 8.0 Hz, 1H), 7.42 (t, J = 7.8 Hz, 1H), 7.25 (d, J = 9.4 Hz, 3H), 7.12 (d, J = 7.6 Hz, 1H), 7.04 (d, J = 8.1 Hz, 2H), 6.94 (s, 1H), 4.68 (s, 2H), 4.16 (t, J = 6.6 Hz, 2H), 2.33 (s, 3H), 1.71-1.63 (m, 2H), 1.47-1.38 (m, 2H), 0.99 (t, J = 7.4 Hz, 3H). 13C NMR (126 MHz, CDCl3): δ = 164.5, 143.9, 136.4, 136.1, 133.5, 130.6, 129.3, 128.7, 128.3, 127.4, 127.2, 127.1, 125.6, 64.9, 44.5, 30.9, 21.6, 19.4, 13.9. HRMS: [M + H]+ calculated for C21H24NO4S: 386.14206, found 386.14194.

Benzyl 1-tosyl-1,2-dihydroquinoline-3-carboxylate (3d). 88% yield. 1H NMR (500 MHz, CDCl3): δ = 7.75 (d, J = 8.1 Hz, 1H), 7.44-7.37 (m, 6H), 7.25-7.22 (m, 1H), 7.19-7.16 (m, 2H), 7.10 (dd, J = 7.6, 1.5 Hz, 1H), 6.96 (s, 1H), 6.86 (d, J = 7.9 Hz, 2H), 5.20 (s, 2H), 4.69 (d, J = 1.2 Hz, 2H), 2.24 (s, 3H). 13C NMR (126 MHz, CDCl3): δ = 164.2, 143.9, 136.4, 136.0, 135.9, 133.9, 130.7, 129.2, 128.8, 128.7, 128.6, 128.2, 127.5, 127.1, 127.1, 125.2, 66.7, 44.5, 21.6. HRMS: [M + H]+ calculated for C24H22NO4S: 420.12641, found 420.12616.

Ethyl 6-methyl-1-tosyl-1,2-dihydroquinoline-3-carboxylate (3e).77% yield. 1H NMR (500 MHz, CDCl3): δ = 7.63 (d, J = 8.2 Hz, 1H), 7.27-7.25 (m, 2H), 7.21 (dd, J = 8.2, 1.5 Hz, 1H), 7.04 (d, J = 8.0 Hz, 2H), 6.91 (d, J = 6.8 Hz, 2H), 4.64 (d, J = 0.9 Hz, 2H), 4.21 (q, J = 7.1 Hz, 2H), 2.35 (s, 3H), 2.33 (s, 3H), 1.31 (t, J = 7.1 Hz, 3H). 13C NMR (126 MHz, CDCl3): δ = 164.5, 143.8, 137.0, 136.1, 133.9, 133.7, 131.4, 129.2, 129.0, 128.0, 128.0, 127.2, 125.4, 60.9, 44.6, 21.6, 21.0, 14.5. HRMS: [M + H]+ calculated for C20H22NO4S: 372.12641, found 372.12631.

Ethyl 6-fluoro-1-tosyl-1,2-dihydroquinoline-3-carboxylate (3f). 83% yield. 1H NMR (400 MHz, CDCl3): δ = 7.73 (dd, J = 8.9, 5.1 Hz, 1H), 7.27-7.24 (m, 2H), 7.09 (ddd, J = 14.7, 10.2, 5.5 Hz, 3H), 6.86 (s, 1H), 6.82 (dd, J = 8.2, 2.9 Hz, 1H), 4.66 (s, 2H), 4.23 (q, J = 7.1 Hz, 2H), 2.34 (s, 3H), 1.32 (t, J = 7.1 Hz, 3H). 13C NMR (101 MHz, CDCl3): δ = 164.1, 161.1 (d, J = 245.9 Hz), 144.1, 135.7, 132.4 (d, J = 2.2 Hz), 132.2 (d, J = 3.0 Hz), 129.8 (d, J = 8.4 Hz), 129.4 (d, J = 8.4 Hz), 129.4, 127.2, 127.0, 117.3 (d, J = 22.9 Hz), 114.7 (d, J = 23.4 Hz), 61.0, 44.37, 21.5, 14.2. HRMS: [M + NH4]+ calculated for C19H22FN2O4S: 393.12788, found 393.12784.

Ethyl 6-chloro-1-tosyl-1,2-dihydroquinoline-3-carboxylate (3g). 81% yield. 1H NMR (500 MHz, CDCl3): δ = 7.70 (d, J = 8.6 Hz, 1H), 7.36 (dd, J = 8.6, 2.4 Hz, 1H), 7.27 (d, J = 8.4 Hz, 2H), 7.10 (d, J = 2.4 Hz, 1H), 7.08 (d, J = 8.1 Hz, 2H), 6.87 (s, 1H), 4.66 (d, J = 1.0 Hz, 2H), 4.23 (q, J = 7.1 Hz, 2H), 2.35 (s, 3H), 1.32 (t, J = 7.1 Hz, 3H). 13C NMR (126 MHz, CDCl3): δ = 164.0, 144.2, 135.8, 134.8, 132.6, 132.2, 130.3, 129.5, 129.5, 128.7, 128.1, 127.1, 126.9, 61.2, 44.5, 21.7, 14.4. HRMS: [M + H]+ calculated for C19H19ClNO4S: 392.07178, found 392.07126.

Ethyl 6-bromo-1-tosyl-1,2-dihydroquinoline-3-carboxylate (3h). 82% yield. 1H NMR (500 MHz, CDCl3): δ = 7.63 (d, J = 8.6 Hz, 1H), 7.51 (dd, J = 8.6, 2.3 Hz, 1H), 7.27 (dd, J = 10.5, 5.3 Hz, 3H), 7.08 (d, J = 8.1 Hz, 2H), 6.87 (s, 1H), 4.66 (d, J = 1.1 Hz, 2H), 4.22 (q, J = 7.1 Hz, 2H), 2.35 (s, 3H), 1.32 (t, J = 7.1 Hz, 3H). 13C NMR (126 MHz, CDCl3): δ = 164.0, 144.2, 135.8, 135.3, 133.3, 132.1, 131.1, 129.9, 129.5, 128.9, 127.1, 126.9, 120.4, 61.2, 44.4, 21.7, 14.4. HRMS: [M + H]+ calculated for C19H19BrNO4S: 436.02127, found 436.02060.

Benzyl 6-methyl-1-tosyl-1,2-dihydroquinoline-3-carboxylate (3i). 85% yield. 1H NMR (500 MHz, CDCl3): δ = 7.63 (d, J = 8.2 Hz, 1H), 7.44-7.38 (m, 5H), 7.21 (dd, J = 8.2, 1.5 Hz, 1H), 7.17 (d, J = 8.3 Hz, 2H), 6.92-6.89 (m, 2H), 6.85 (d, J = 8.1 Hz, 2H), 5.19 (s, 2H), 4.66 (s, 2H), 2.34 (s, 3H), 2.24 (s, 3H). 13C NMR (126 MHz, CDCl3): δ = 164.2, 137.0, 136.0, 135.9, 134.1, 133.9, 131.5, 129.2, 129.1, 128.8, 128.7, 128.6, 128.0, 127.3, 127.1, 125.0, 66.6, 44.6, 21.6, 21.0. HRMS: [M + H]+ calculated for C25H24NO4S: 434.14206, found 434.14191.

Ethyl 7-nitroquinoline-3-carboxylate (3j). 58% yield. By following the mentioned conditions, cyclization occurred but with in situ elimination of TsH and a quinoline product was isolated. 1H NMR (500 MHz, CDCl3): δ = 9.60 (d, J = 2.1 Hz, 1H), 9.06 (d, J = 2.2 Hz, 1H), 8.95-8.94 (m, 1H), 8.41 (dd, J = 8.9, 2.3 Hz, 1H), 8.13 (d, J = 8.9 Hz, 1H), 4.53 (q, J = 7.1 Hz, 2H), 1.49 (t, J = 7.1 Hz, 3H). 13C NMR (101 MHz, CDCl3): δ = 165.6, 150.2, 145.0, 138.8, 131.9, 129.7, 129.2, 127.6, 127.0, 123.5, 61.7, 14.5. HRMS: [M + H]+ calculated for C12H11N2O4: 247.07133, found 247.07147.

Quinoline-3-carbonitrile (3k). 52% yield. By following the optimized conditions, cyclization occurred but with in situ elimination of TsH and a quinoline product was isolated. 1H NMR (400 MHz, CDCl3): δ = 9.04 (d, J = 1.6 Hz, 1H), 8.54 (s, 1H), 8.18 (d, J = 8.8 Hz, 1H), 7.95-7.85(m, 2H), 7.70 (t, J = 7.9 Hz, 1H). 13C NMR (101 MHz, CDCl3): δ = 149.88, 148.98, 141.55, 132.87, 130.03, 128.62, 128.37, 126.36, 117.20, 106.77. HRMS: [M + H]+ calculated for C10H7N2: 155. 0609, found 155. 0608.

3-(phenylsulfonyl)quinoline (3l). 56% yield. By following the mentioned conditions, cyclization occurred but with in situ elimination of TsH and a quinoline product was isolated. 1H NMR (400 MHz, CDCl3): δ = 9.28 (d, J = 1.8 Hz, 1H), 8.82 (s, 1H), 8.16 (d, J = 8.4 Hz, 1H), 8.04 (d, J = 7.5 Hz, 2H), 7.96 (d, J = 8.1 Hz, 1H), 7.87 (t, J = 7.8 Hz, 1H), 7.67 (t, J = 7.6 Hz, 1H), 7.56 (m, 3H). 13C NMR (101 MHz, CDCl3): δ = 149.52, 147.23, 141.20, 136.99, 134.90, 133.83, 132.85, 129.77, 129.70, 129.29, 128.47, 127.93, 126.50. HRMS: [M + H]+ calculated for C15H12NO2S: 270.0589, found 270.0582.

6. Conclusions

We developed a Rh(Ⅲ)-catalyzed annulation of N-(2- formylphenyl)-4-methylbenzenesulfonamide derivatives and used activated olefins for the synthesis of 1,2-dihydroquinoline and other quinolines. Various functional groups are compatible under these conditions, and two categories of heterocycles were isolated as a result of substrate control. The reaction were conducted under simple conditions with a low catalyst loading. Studies to further understand the catalytic pathway and for the application of this methodology to synthesis of complex natural products are currently underway in our laboratory.

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