Synthesis of α-Alkoxycarbonyl-α-siloxyamides by the Reaction of a Carbamoylsilane with α-Ketoesters

doi:10.6023/cjoc201703018

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (9): 2423-2429.DOI: 10.6023/cjoc201703018 Previous Articles Next Articles

Notes

氨甲酰基硅烷与α-羰基酯反应合成α-硅氧基-α-烷氧羰基酰胺衍生物

李伟东^a, 韩生华^b, 刘艳红^a, 陈建新^a

a 山西师范大学化学与材料科学学院临汾 041004;
b 山西大同大学化学与工程学院大同 037009

收稿日期:2017-03-08 修回日期:2017-04-17 发布日期:2017-05-17
通讯作者: 陈建新 E-mail:jjxxcc2002@yahoo.com
基金资助:
山西省留学回国人员基金（No.0713）、山西省自然科学基金（No.2012011046-9）和山西师范大学文理学院基金（No.WL2016CXCY-YJ-30）资助项目.

Synthesis of α-Alkoxycarbonyl-α-siloxyamides by the Reaction of a Carbamoylsilane with α-Ketoesters

Li Weidong^a, Han Shenghua^b, Lui Yanhong^a, Chen Jianxin^a

a College of Chemistry and Material Science, Shanxi Normal University, Linfen 041004;
b College of Chemistry and Engineering, Shanxi Datong University, Datong 037009

Received:2017-03-08 Revised:2017-04-17 Published:2017-05-17
Contact: 10.6023/cjoc201703018 E-mail:jjxxcc2002@yahoo.com
Supported by:
Project supported by the Shanxi Province Foundation for Returness Overseas Scientists (No. 0713), the Natural Science Foundation of Shanxi Province (No. 2012011046-9), and the Foundation of the Modern College of Arts and Science, Shanxi Normal University (No. WL2016CXCY-YJ-30).

1. Synthesis of α-Alkoxycarbonyl-α-siloxyamides by the Reaction of a Carbamoylsilane with α-Ketoesters.PDF(691KB)

Abstract

N,N-Dimethylcarbamoyl(trimethyl)silane reacted with a series of α-ketoesters in anhydrous toluene at 60℃ to afford α-alkoxycarbonyl-α-siloxy amide derivatives in good yields (70%~99%). When the alkyl of α-ketoesters was L-2-isopropyl-5-methylcyclohexyl, the reactions possess stereo selectivity. The experimental results showed that the electronic property of the substituted group on the aryl ring affected both the reaction ratio and the yields of products. The structures of the products were characterized by element analysis, ¹H NMR, ¹³C NMR and IR spectra. A reaction mechanism is proposed. The mild and no catalyst conditions, simple procedure, less byproducts and good yields provide an effective method for the preparation of α-alkoxycarbonyl-α-hydroxy amides.

Key words: carbamoylsilane, α-ketoesters, α-alkoxycarbonyl-α-hydroxyamides, nucleophilic addition, synthetic methods

Cite this article

Li Weidong, Han Shenghua, Lui Yanhong, Chen Jianxin. Synthesis of α-Alkoxycarbonyl-α-siloxyamides by the Reaction of a Carbamoylsilane with α-Ketoesters[J]. Chin. J. Org. Chem., 2017, 37(9): 2423-2429.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Miao, C.-B.; Wang, Y.-H.; Xing, M.-L.; Lu, X.-W.; Sun, X.-Q.; Yang, H.-T. J. Org. Chem. 2013, 78, 11584.
[2] Park, J.-H.; Chang, J.-S.; El-Gamal, M. I.; Choi, W.-K.; Lee, W. S.; Chung, H. J.; Kim, H.-I.; Cho, Y.-J.; Lee, B.-S.; Jeon, H. R.; Lee, Y. S.; Choi, Y. W.; Lee, J.; Oh, C. H. Bioorg. Med. Chem. Lett. 2010, 20, 5895.
[3] Pritchard, D. R.; Wilden, J. D. Tetrahedron Lett. 2010, 51, 1819.
[4] Siliphaivanh, P.; Harrington, P.; Witter, D.; Ott, K.; Tempest, P.; Kattar, S.; Kral, A. M.; Fleming, J. C.; Deshmukh, S. V.; Harsch, A. Bioorg. Med. Chem. Lett. 2007, 17, 4619.
[5] Amada, H.; Matsuda, D.; Bohno, A. WO 2011034215, 2011[Chem. Abstr. 2011, 154, 385279].
[6] Yang, K.; Huang, J.; Eisele, F. WO 2013163889, 2013[Chem. Abstr. 2013, 159, 699243].
[7] Zhu, J.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron Lett. 1994, 35, 2787.
[8] Christoffers, J.; Werner, T.; Frey, W.; Baro, A. Chem.-Eur. J. 2004, 10, 1042.
[9] Wellington, K. D.; Cambie, R. C.; Rutledge, P. S.; Bergquist, P. R. J. Nat. Prod. 2000, 63, 79.
[10] Racv, L. D.; Frey, W.; Ivanov, I. C. Synlett 2004, 1584.
[11] Christoffers, J.; Baro, A.; Werner, T. Adv. Synth. Catal. 2004, 346, 143.
[12] Zhang, J.; Sarma, K. D.; Curran. T. T.; Belmont, D. T.; Davidson, J. G. J. Org. Chem. 2005, 70, 5890.
[13] Li, S.; Wang, S. J. Heterocycl. Chem. 2008, 45, 1875.
[14] Wang, J.-W.; Yuan, Y.-C.; Xiong, R.; Zhang, D.; Du, Y.-F.; Zhao, K. Org. Lett. 2012, 14, 2210.
[15] Li, Z.; Lian, M.; Yang, F.; Meng, Q.; Gao, Z. Eur. J. Org. Chem. 2014, 3491.
[16] Zou, L.; Wang, B.; Mu, H.; Zhang, H.; Song, Y.; Qu, J. Org. Lett. 2013, 15, 3106.
[17] Li, D.-M.; Schroder, K.; Bitterlich, B.; Tse, M. K.; Beller, M. Tetrahedron Lett. 2008, 49, 5976.
[18] Liang, Y.-F.; Jiao, N. Angew. Chem., Int. Ed. 2014, 53, 548.
[19] Yu, J.; Cui, J.-A.; Zhang, C. Eur. J. Org. Chem. 2010, 7020.
[20] Asahara, H.; Nishiwaki, N. J. Org. Chem. 2014, 79, 11735.
[21] Li, F.; Zhou, W.; Zheng, L.-S.; Li, L.; Zheng, Z.-J.; Xu, L.-W. Synth. Commun. 2014, 44, 2861.
[22] Dong, C.; Song, T.; Bei, X.-F.; Cui, Y.-M.; Xu, Z.; Xu, L.-W. Catal. Sci. Technol. 2015, 5, 4755.
[23] Xing, P.; Zang, W.; Huang, Z.-G.; Zhan, Y.-X.; Zhu, C.-J.; Jing, B. Synlett 2012, 2269.
[24] Wei, Y.-L.; Huang, W.-S.; Cui, Y.-M.; Yang, K.-F.; Xu, Z.; Xu, L.-W. RSC Adv. 2015, 5, 3098.
[25] Tong, W.-T.; Liu, H.; Chen, J.-X. Tetrahedron Lett. 2015, 56, 1335.
[26] Liu, H.; Guo, Q.-L.; Chen, J.-X. Tetrahedron Lett. 2015, 56, 5747.
[27] Guo, Q.-L.; Wen, X.-P.; Chen, J.-X. Tetrahedron 2016, 72, 8117.
[28] Yao, Y.; Li, W.-T.; Chen, J.-X. Chin. J. Org. Chem. 2014, 34, 2124(in Chinese). (姚远, 李伟东, 陈建新, 有机化学, 2014, 34, 2124.)
[29] Yao, Y.; Li, W.-T.; Tong, W.-T.; Chen, J.-X. Chin. J. Org. Chem. 2015, 35, 223(in Chinese). (姚远, 李伟东, 仝文婷, 陈建新, 有机化学, 2015, 35, 223.)
[30] Liu, Y.-H.; Cao, P.; Chen, J.-X. Tetrahedron Lett. 2016, 57, 937.
[31] Ma, F.; Liu, H.; Chen, J.-X. Tetrahedron Lett. 2016, 57, 5246.
[32] Li, W.-D.; Liu, Y.-H.; Chen, J.-X. Tetrahedron Lett. 2015, 56, 4328.
[33] Chen, J.-X.; Cunico, R. F. Tetrahedron Lett. 2002, 43, 8595.
[34] Cunico, R. F.; Pandey, R. K. J. Org. Chem. 2005, 70, 9048.
[35] Cunico, R. F.; Chen, J.-X. Synth. Commun. 2003, 33, 1963.
[36] Xiang, J.-M.; Chen, J.-C.; Li, B.-L. Chin. J. Org. Chem. 2009, 29, 392(in Chinese). (向纪明, 陈久存, 李宝林, 有机化学, 2009, 29, 392.)
[37] Meng, Q.-H.; Zhu, L.-F.; Zhang, Z.-G. J. Org. Chem. 2008, 73, 7209.
[38] Xiang, J.-M.; Li, B.-L. Chem. J. Chin. Univ. 2010, 31, 68(in Chinese). (向纪明, 李宝林, 高等学校化学学报, 2010, 31, 68.)

氨甲酰基硅烷与α-羰基酯反应合成α-硅氧基-α-烷氧羰基酰胺衍生物

Synthesis of α-Alkoxycarbonyl-α-siloxyamides by the Reaction of a Carbamoylsilane with α-Ketoesters

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Li Guan, Yanyan Zhou, Yongbao Mao, Kaisen Fu, Wenhui Guan, Yile Fu. Research Progress in the Synthesis of Polymethine Chain Modified Cyanine Dyes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2682-2698.
[2]	Peng Liu, Fuming Zhong, Lihao Liao, Weiqiang Tan, Xiaodan Zhao. Progress in the Construction of Spirocyclohexadienones via Alkyne-Involving Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4019-4035.
[3]	Junjiao Wang, Yuyu Lv, Yongwei Shang, Zhenli Cui, Ke-Hu Wang, Danfeng Huang, Yulai Hu. Research Progress of Reactions Participated by α-Hydroxy Ketones [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2300-2321.
[4]	Wenqi Liu, Zhenlu Shen, Senmiao Xu. Synthesis of 1,1-Diboron Alkanes via Diborylation of Unactivated Primary C(sp³)—H Bonds Enabled by AsPh₃/Iridium Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1101-1110.
[5]	Wenpeng Wang, Chunhong Yang, Haichao Liu, Xicun Wang, Zhengjun Quan. Addition of Benzyne to 2-Hydroxypyrimidine to Synthesize 2-Aryloxypyrimidine Derivatives under Mild Conditions [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3835-3842.
[6]	Junfei Li, Yuling Han, Yanhong Liu, Jianxin Chen. Synthesis of β-Nitroamide Derivatives Based on Carbamoylsilane [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3880-3889.
[7]	Shuowen Wang, Pingyu Jiang, Rong Li, Muyang Yang, Guojun Deng. Progress in Selective Construction of Functional Aromatics with Cyclohexanone [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 129-146.
[8]	Xiaoliang Zou, Senmiao Xu. Recent Progress in Iridium-Catalyzed Remote Regioselective C—H Borylation of (Hetero)Arenes [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2610-2620.
[9]	Luhua Liu, Rongrong Du, Senmiao Xu. Ligand-Free Iridium-Catalyzed Borylation of Secondary Benzylic C—H Bonds [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1572-1581.
[10]	Zhang Pengpeng, Han Shenghua, Chen Jianxin. Efficient Synthesis of β-Keto-α-hydroxy Secondary (Primary) Amides by Selective Aminocarbonylation of Vicinal Diketones Using Carbamoylsilane as an Amide Source [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1737-1744.
[11]	Luo Liang, Cao Xiaomei, Lai Guowei, Liu Jinxiang, Luo Haiqing, Lu Dongliang, Zhang Yong. “On Water” Nucleophilic Addition of Pyrazolones to Trifluoromethyl Ketones [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1323-1330.
[12]	Ma Ben, Wang Ganggang, Zhou Hongyan, Yang Jingya. Alkali Salt-Catalyzed Aza-Michael Addition of 1,2,4-Triazole to α,β-Unsaturated Ketones and Imides [J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 115-124.
[13]	Xu Qing, Zhang Lianyang, Feng Gaofeng, Jin Chengan. Progress on the Synthesis and Applications of Thiocyanates [J]. Chin. J. Org. Chem., 2019, 39(2): 287-300.
[14]	Zhang Pengpeng, Chen Wenwen, Feng Hua, Chen Jianxin. Synthesis of 3-Hydroxy-3-heterocyclebutylamide Derivatives Using Carbamoylsilanes as an Amide Source [J]. Chinese Journal of Organic Chemistry, 2019, 39(12): 3560-3566.
[15]	Li, Xubin, Zhou, Chen, Liu, Xingtong, Wang, Teng, Yu, Xinhong, Ma, Hongmei, Li, Cuiqing. ipso-Oxidation of Allyl Ether/Decarboxylative Aromatization Cascade Strategy via Oxocarbenium Activation: A Novel Approach for Synthesis of N-Alkyl Pyrroles [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2906-2911.