Pyridine Bridged Organocatalyst for the Synthesis of 3-Aryl-2-oxazolidinones from Carbon Dioxide, Terminal Epoxide, and Aryl Amine

doi:10.6023/cjoc201903030

Abstract

A series of carboxyl group or hydroxyl group functionalized organocatalysts were synthesized and applied in three component reaction of carbon dioxide with epoxide, and aryl amines for the synthesis of 3-aryl-2-oxazolidinones. The method allows the reaction to proceed smoothly in the mild reaction conditions, together with excellent substrates scope of epoxides and aryl amines. The control experiments suggest that the cyclic carbonates are formed by the coupling of epoxides with carbon dioxide, which further react with the amino alcohol generated from epoxides and aryl amines, finally resulting in the desired products.

Key words: organocatalyst, carbon dioxide, oxazolidinones, epoxide

Cite this article

Liu, Quanyao, Shi, Lei, Liu, Ning. Pyridine Bridged Organocatalyst for the Synthesis of 3-Aryl-2-oxazolidinones from Carbon Dioxide, Terminal Epoxide, and Aryl Amine[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2882-2891.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 11

Scheme 1. Synthetic pathway of organocatalysts

Entry	Catalyst	Co-catalyst	Yield/%
1	1a	DBU	97
2	1b	DBU	75
3	1c	DBU	62
4	1d	DBU	92
5	1e	DBU	67
6	1f	DBU	89
7	1g	DBU	94
8	1h	DBU	71
9	1i	DBU	96
10	1j	DBU	99
11	1k	DBU	81
12	1l	DBU	67
13	1j	—	Trace
14	—	DBU	37

Table 1. Structure-activity relationship of catalysts

Entry	1j/ mmol	DBU/ mmol	PO/ mL	CO₂/ kPa	Time/ h	Temp./ ℃	Yield/%
1	0.1	0.4	2	500	6	100	99
2	0.1	0.4	2	500	6	90	99
3	0.1	0.4	2	500	6	80	97
4	0.1	0.4	2	500	6	70	35
5	0.1	0.4	2	500	4	80	96
6	0.1	0.4	2	500	3	80	65
7	0.1	0.4	2	300	4	80	91
8	0.05	0.4	2	300	4	80	45
9	0.05	0.4	2	300	4	90	90
10	0.05	0.4	1.5	300	4	90	86
11	0.05	0.4	1	300	4	90	71
12	0.05	0.6	1	300	4	90	96
13	0.05	0.6	1	100	4	90	10

Table 2. Optimization of reaction condition

Table 3. Scope of substrates

Scheme 2. Study on the reaction of PO with CO2

Scheme 3. Study on the reaction of PO with aniline

Scheme 4. Study on the reaction of PC with amino alcohol

Scheme 5. Study on the reaction of PC with aniline

Figure 1. 1H NMR spectra of only aniline (0.5 mmol) (a), and the mixture of aniline (0.5 mmol) and DBU (0.5 mmol) (b) in CD3CN (0.5 mL)

Figure 2. 1H NMR spectra of only amino alcohol (0.5 mmol) (a) and the mixture of amino alcohol (0.5 mmol) and DBU (0.5 mmol) (b) in CD3CN (0.5 mL)

Figure 3. Cooperative catalytic mechanism between organocatalyst and DBU

References 20

[1]	(a) Niemi, T.; Repo, T. Eur. J. Org. Chem. 2019,1180.
	(b) Chellat, M. F.; Raguž, L.; Riedl, R. Angew. Chem., Int. Ed. 2016, 55, 6600.
	(c) Niemi, T.; Perea-Buceta, J. E.; Fernández, I.; Alakurtti, S.; Rantala, E.; Repo, T. Chem.-Eur. J. 2014, 20, 8867.
	(d) Dinsmore, C. J.; Mercer, S. P. Org. Lett. 2004, 6, 2885.
[2]	(a) Chen, G.; Fu, C.; Ma, S . Org. Lett. 2009, 11, 2900.
	(b) Li, S.; Ye, J.; Yuan, W.; Ma, S . Tetrahedron. 2013, 69 10450.
[3]	(a) Kayaki, Y.; Mori, N.; Ikariya, T . Tetrahedron Lett. 2009, 50, 6491. doi: 10.1016/j.tetlet.2009.09.015
	(b) Yamashita, K.; Hase, S.; Kayaki, Y.; Ikariya, T . Org. Lett. 2015, 17, 2334. doi: 10.1016/j.tetlet.2009.09.015
[4]	(a) Wang, X.; Gao, W.-Y.; Niu, Z.; Wojtas, L.; Perman, J. A.; Chen, Y.-S.; Li, Z.; Aguila, B.; Ma, S . Chem. Commun. 2018, 54, 1170.
	(b) Dabral, S.; Schaub, T. Adv. Synth. Catal. 2019, 361, 223.
	(c) Adhikari, D.; Miller, A. W.; Baik, M.-H.; Nguyen, S. T . Chem. Sci. 2015, 6, 1293.
	(d) Liu, A.-H.; Dang, Y.-L.; Zhou, H.; Zhang, J.-J.; Lu, X.-B . ChemCatChem 2018, 10 2686.
	(e) Seayad, J.; Seayad, A. M.; Ng, J. K. P.; Chai, C. L. L . ChemCatChem 2012, 4 774.
	(f) Saptal, V. B.; Bhanage, B. M . ChemSusChem. 2016, 9 1980.
	(g) Liu, X.-F.; Wang, M.-Y.; He, L.-N . Curr. Org. Chem. 2017, 21, 698.
	(h) Phung, C.; Ulrich, R. M.; Ibrahim, M.; Tighe, N. T. G.; Lieberman, D. L.; Pinhas, A. R . Green Chem. 2011, 13, 3224.
	(i) Yang, Z.-Z.; Li, Y.-N.; Wei, Y.-Y.; He, L.-N . Green Chem. 2011, 13, 2351.
	(j) Chen, Y.; Luo, R.; Yang, Z.; Zhou, X.; Ji, H . Sustainable Energy Fuels. 2018, 2 125.
	(k) Kathalikkattil, A. C.; Tharun, J.; Roshan, R.; Soek, H.-G.; Park, D.-W . Appl. Catal., A 2012, 447-448, 107.
	(l) Zhao, Y.-N.; Yang, Z.-Z.; Luo, S.-H.; He, L.-N . Catal. Today 2013, 200 2.
[5]	(a) Ye, J.-H.; Song, L.; Zhou, W.-J.; Ju, T.; Yin, Z.-B.; Yan, S.-S.; Zhang, Z.; Li, J.; Yu, D.-G. Angew. Chem., Int. Ed. 2016, 55, 10022.
	(b) Wang, M.-Y.; Cao, Y.; Liu, X.; Wang, N.; He, L.-N.; Li, S.-H . Green Chem. 2017, 19, 1240.
	(c) Yin, Z.-B.; Ye, J.-H.; Zhou, W.-J.; Zhang, Y.-H.; Ding, L.; Gui, Y.-Y.; Yan, S.-S.; Li, J.; Yu, D.-G . Org. Lett. 2018, 20, 190.
	(d) Sun, L.; Ye, J.-H.; Zhou, W.-J.; Zeng, X.; Yu, D.-G . Org. Lett. 2018, 20, 3049.
	(e) Takeda, Y.; Okumura, S.; Tone, S.; Sasaki, I.; Minakata, S . Org. Lett. 2012, 14, 4874.
[6]	(a) Peshkov, V. A.; Pereshivko, O. P.; Nechaev, A. A.; Peshkov, A. A.; Van der Eycken, E. V . Chem. Soc. Rev. 2018, 47, 3861.
	(b) Brunel, P.; Monot, J.; Kefalidis, C. E.; Maron, L.; Martin-Vaca, B.; Bourissou, D . ACS Catal. 2017, 7, 2652.
	(c) Chang, Z.; Jing, X.; He, C.; Liu, X.; Duan, C . ACS Catal. 2018, 8, 1384.
	(d) Zhao, Y.; Qiu, J.; Tian, L.; Li, Z.; Fan, M.; Wang, J . ACS Sustainable Chem. Eng. 2016, 4, 5553.
	(e) Hu, J.; Ma, J.; Zhu, Q.; Zhang, Z.; Wu, C.; Han, B . Angew. Chem., Int. Ed. 2015, 54, 5399.
	(f) García-Domínguez, P.; Fehr, L.; Rusconi, G.; Nevado, C . Chem. Sci. 2016, 7, 3914.
	(g) Liu, X.; Wang, M.-Y.; Wang, S.-Y.; Wang, Q.; He, L.-N . ChemSusChem. 2017, 10 1210.
	(h) Hu, J.; Ma, J.; Zhang, Z.; Zhu, Q.; Zhou, H.; Lu, W.; Han, B . Green Chem. 2015, 17, 1219.
	(i) Zhao, D.; Liu, X.-H.; Zhu, C.; Kang, Y.-S.; Wang, P.; Shi, Z.; Lu, Y.; Sun, W.-Y . ChemCatChem. 2017, 9 4598.
	(j) Yang, H.; Zhang, X.; Zhang, G.; Fei, H . Chem. Commun. 2018, 54, 4469.
[7]	(a) Rintjema, J.; Epping, R.; Fiorani, G.; Martín, E.; Escudero- Adán, E. C.; Kleij, A. W. Angew. Chem., Int. Ed. 2016, 55, 3972.
	(b) Rintjema, J.; Guo, W.; Martin, E.; Escudero-Adán, E. C.; Kleij, A. W. Chem.-Eur. J. 2015, 21, 10754.
	(c) Lee, Y.; Choi, J.; Kim, H . Org. Lett. 2018, 20, 5036.
[8]	(a) Zhang, G.; Yang, H.; Fei, H . ACS Catal. 2018, 8, 2519.
	(b) Song, Q.-W.; Zhou, Z.-H.; Wang, M.-Y.; Zhang, K.; Liu, P.; Xun, J.-Y.; He, L.-N. ChemSusChem 2018, 9, 2054.
	(c) Song, Q.-W.; Chen, W.-Q.; Ma, R.; Yu, A.; Li, Q.-Y.; Chang, Y.; He, L.-N . ChemSusChem 2015, 8, 821.
	(d) Song, Q.-W.; Liu, P.; Han, L.-H.; Zhang, K.; He, L.-N . Chin. J. Chem. 2018, 36, 147.
	(e) Li, X.-D.; Song, Q.-W.; Lang, X.-D.; Chang, Y.; He, L.-N . ChemPhysChem. 2017, 18 3182.
	(f) Li, X.-D.; Lang, X.-D.; Song, Q.-W.; Guo, Y.-K.; He, L.-N . Chin. J. Org. Chem. 2016, 36, 744 (in Chinese).
	( 李雪冬, 郎咸东, 宋清文, 郭亚坤, 何良年 , 有机化学, 2016, 36, 744-751.)
[9]	(a) Niemi, T.; Perea-Buceta, J. E.; Fernández, I.; Hiltunen, O.-M.; Salo, V.; Rautiainen, S.; Räisänen, M. T.; Repo, T . Chem.-Eur. J. 2016, 22, 10355.
	(b) Mei, C.; Zhao, Y.; Chen, Q.; Cao, C.; Pang, G.; Shi, Y . ChemCatChem 2018, 10, 3057-3068.
[10]	(a) Wang, B.; Yang, S.; Min, L.; Gu, Y.; Zhang, Y.; Wu, X.; Zhang, L.; Elageed, E. H. M.; Wu, S.; Gao, G. Adv. Synth. Catal. 2014, 356, 3125.
	(b) Zhang, L.; Fu, X.; Gao, G. ChemCatChem 2011, 3, 1359.
	(c) Selva, M.; Fabris, M.; Lucchini, V.; Perosa, A.; Noè, M . Org. Biomol. Chem. 2010, 8, 5187.
	(d) Lang, X.-D.; Li, Z.-M.; He, L.-N . Catal. Today 2019, 324 167.
	(e) Hang, G.; Nian-Fa, Y.; Guo-Jun, D.; Guang-Yi, X . Chem. Lett. 2009, 38, 584.
	(f) Zhang, Y.; Wang, B.; Elageed, E. H. M.; Qin, L.; Ni, B.; Liu, X.; Gao, G . ACS Macro Lett. 2016, 5, 435.
[11]	Wang, B.; Elageed, E. H. M.; Zhang, D.; Yang, S.; Wu, S.; Zhang, G.; Gao, G. ChemCatChem 2014, 6, 278. doi: 10.1002/cctc.201300801
[12]	Hosseinian, A.; Ahmadi, S.; Mohammadi, R.; Monfared, A.; Rahmani, Z. J. CO2 Util. 2018, 27, 381.
[13]	Wang, B.; Luo, Z.; Elageed, E. H.M.; Wu, S.; Zhang, Y.; Wu, X.; Xia, F.; Zhang, G.; Gao, G ChemCatChem. 2016, 8 830. doi: 10.1002/cctc.v8.4
[14]	Lv, M.; Wang, P.; Yuan, D.; Yao, Y . ChemCatChem. 2017, 9 4451. doi: 10.1002/cctc.201700594
[15]	Seo, U. R.; Chung, Y. K. Green Chem. 2017, 19, 803. doi: 10.1039/C6GC02934E
[16]	Sadeghzadeh, S. M.; Zhiani, R.; Emrani, S . Catal. Lett. 2018, 148, 119. doi: 10.1006/jcat.1994.1192
[17]	Xu, B.; Wang, P.; Lv, M.; Yuan, D.; Yao, Y . ChemCatChem. 2016, 8 2466. doi: 10.1002/cctc.201600534
[18]	Chen, F.; Li, M.; Wang, J.; Dai, B.; Liu, N. J. CO₂ Util. 2018, 28, 181.
[19]	(a) Wang, L.; Liu, N.; Dai, B.; Hu, H. Eur. J. Org. Chem. 2014, 2014, 6493.
	(b) Liu, Q.-Y.; Shi, L.; Liu, N. J. Chem. Res. 2019, 43, 248.
[20]	Wang, P.; Qin, J.; Yuan, D.; Wang, Y.; Yao, Y . ChemCatChem. 2015, 7 1145. doi: 10.1002/cctc.201403015

吡啶桥连双功能有机催化剂催化二氧化碳、环氧化物和芳香胺合成3-芳基-2-噁唑烷酮的研究