The Efficient Synthesis of 2-(3-Carbamoylpyridine-2-yl) Nicotinamide Pyridine
Salts

Lei-Yang       Zhang; Jing-Bo       Geng; Nai-Xing       Wang; Yue-Hua       Wu; Zhan       Yan; Bao-Cai       Xu; Yalan       Xing

doi:10.2174/1570178618666210706112141

Abstract

The synthesis of axially chiral compounds has attracted a great deal of attention in recent years. Herein, an efficient and economical synthetic route has been developed for 2-(3- carbamoylpyridin-2-yl) nicotinamide pyridine salts, axially chiral compounds. The starting material 1,10-phenanthroline is readily available. In this study, 2-(3-carbamoylpyridin-2-yl) nicotinamide pyridine salts are obtained in moderate to good yields. This protocol includes simple operations and has easy scalability. In addition, the axial chirality of the products is also preliminary studied.

Keywords: NADH model, NAD+ compound, binicotinamide pyridine salts, axial chirality, 1, 10-phenanthroline, scalable.

« Previous Next »

Graphical Abstract

[1] 
Koga, K.; Matsubara, Y.; Kosaka, T.; Koike, K.; Morimoto, T.; Ishitani, O. Organometallics,  2015, 34, 5530-5539.
[http://dx.doi.org/10.1021/acs.organomet.5b00713] 
[2] 
Htet, Y.; Tennyson, A.G. J. Am. Chem. Soc.,  2016, 138(49), 15833-15836.
[http://dx.doi.org/10.1021/jacs.6b10451] [PMID:  27960347] 
[3] 
Betanzos-Lara, S.; Liu, Z.; Habtemariam, A.; Pizarro, A.M.; Qamar, B.; Sadler, P.J. Angew. Chem. Int. Ed.,  2012, 51, 3897-3900.
[http://dx.doi.org/10.1002/anie.201108175] 
[4] 
Gebicki, J.; Marcinek, A. Zielonka. J. Acc. Chem. Res.,  2004, 37(6), 379-386.
[http://dx.doi.org/10.1021/ar030171j] [PMID:  15196047] 
[5] 
Lee, J. Churchil, H.; Choi, W.B.; Lynch, J.E.; Roberts, F.E.; Volante, R.P.; Reider, P.J. Chem. Commun. (Camb.),  1999, 729-730.
[http://dx.doi.org/10.1039/a809930h] 
[6] 
Ngo, A.H.; Ibañez, M.; Do, L.H. ACS Catal.,  2016, 6, 2637-2641.
[http://dx.doi.org/10.1021/acscatal.6b00395] 
[7] 
Zhang, T.; Bai, C-B.; Wu, Y-H.; Wang, N-X.; Xu, B-C.; Yan, Z.; Xing, Y. Synth. Commun.,  2019, 49, 410-416.
[http://dx.doi.org/10.1080/00397911.2018.1557689] 
[8] 
Zhao, L.; Wei, J.; Lu, J.; He, C.; Duan, C. Angew. Chem. Int. Ed.,  2017, 56, 8692-8696.
[http://dx.doi.org/10.1002/anie.201702926] 
[9] 
Yang, J.D.; Chen, B.L.; Zhu, X.Q. J. Phys. Chem. B,  2018, 122(27), 6888-6898.
[http://dx.doi.org/10.1021/acs.jpcb.8b03453] [PMID:  29886742] 
[10] 
Halle, F.; Fin, A.; Rovira, A.R.; Tor, Y. Angew. Chem. Int. Ed.,  2018, 57, 1087-1090.
[http://dx.doi.org/10.1002/anie.201711935] 
[11] 
Wang, J.; Zhu, Z.H.; Chen, M.W.; Chen, Q.A.; Zhou, Y.G. Angew. Chem. Int. Ed.,  2019, 58, 1813-1817.
[http://dx.doi.org/10.1002/anie.201813400] 
[12] 
Kim, J.; Lee, S.H.; Tieves, F.; Choi, D.S.; Hollmann, F.; Paul, C.E.; Park, C.B. Angew. Chem. Int. Ed.,  2018, 57, 13825-13828.
[http://dx.doi.org/10.1002/anie.201804409] 
[13] 
Kuk, S.K.; Gopinath, K.; Singh, R.K.; Kim, T-D.; Lee, Y.; Choi, W.S.; Lee, J-K.; Park, C.B. ACS Catal.,  2019, 9, 5584-5589.
[http://dx.doi.org/10.1021/acscatal.9b00127] 
[14] 
Tensi, L.; Macchioni, A. ACS Catal.,  2020, 10, 7945-7949.
[http://dx.doi.org/10.1021/acscatal.0c02261] 
[15] 
Iorgu, A.I.; Baxter, N.J.; Cliff, M.J.; Levy, C.; Waltho, J.P.; Hay, S.; Scrutton, N.S. ACS Catal.,  2018, 8(12), 11589-11599.
[http://dx.doi.org/10.1021/acscatal.8b02810] [PMID:  31119061] 
[16] 
Yadav, R.K.; Oh, G.H.; Park, N.J.; Kumar, A.; Kong, K.J.; Baeg, J.O. J. Am. Chem. Soc.,  2014, 136(48), 16728-16731.
[http://dx.doi.org/10.1021/ja509650r] [PMID:  25405924] 
[17] 
Oppelt, K.T.; Gasiorowski, J.; Egbe, D.A.; Kollender, J.P.; Himmelsbach, M.; Hassel, A.W.; Sariciftci, N.S.; Knör, G. J. Am. Chem. Soc.,  2014, 136(36), 12721-12729.
[http://dx.doi.org/10.1021/ja506060u] [PMID:  25130570] 
[18] 
Kwok, C.L.; Cheng, S.C.; Ho, P.Y.; Yiu, S.M.; Man, W.L.; Au, V.K.; Tsang, P.K.; Leung, C.F.; Ko, C.C.; Robert, M. Chem. Commun. (Camb.),  2020, 56(54), 7491-7494.
[http://dx.doi.org/10.1039/D0CC02604B] [PMID:  32497158] 
[19] 
Nakano, Y.; Black, M.J.; Meichan, A.J.; Sandoval, B.A.; Chung, M.M.; Biegasiewicz, K.F.; Zhu, T.; Hyster, T.K. Angew. Chem. Int. Ed.,  2020, 59, 10484-10488.
[http://dx.doi.org/10.1002/anie.202003125] 
[20] 
Xing, Y.; Wang, N-X.; Bai, C-B.; Lan, X-W. Synlett,  2016, 28, 402-414.
[http://dx.doi.org/10.1055/s-0036-1588665] 
[21] 
Wang, N-X. Zhao. J. Adv. Synth. Catal.,  2009, 351, 3045-3050.
[http://dx.doi.org/10.1002/adsc.200900610] 
[22] 
Bai, C.B.; Wang, N.X.; Wang, Y.J.; Xing, Y.; Zhang, W.; Lan, X.W. Sci. Rep.,  2015, 5, 17458.
[http://dx.doi.org/10.1038/srep17458] [PMID:  26648413] 
[23] 
Zhao, J.; Wang, N-X.; Wang, W-W.; Wang, G.X.; Liu, Y.H.; Li, L.; Yu, J-L.; Tang, X-L. Molecules,  2007, 12(5), 979-987.
[http://dx.doi.org/10.3390/12050979] [PMID:  17873833] 
[24] 
Metz, A.E.; Podlesny, E.E.; Carroll, P.J.; Klinghoffer, A.N.; Kozlowski, M.C. J. Am. Chem. Soc.,  2014, 136(30), 10601-10604.
[http://dx.doi.org/10.1021/ja506137j] [PMID:  25019179] 
[25] 
Brunel, J.M. Chem. Rev.,  2005, 105(3), 857-897.
[http://dx.doi.org/10.1021/cr040079g] [PMID:  15755079] 
[26] 
Berthod, M.; Mignani, G.; Woodward, G.; Lemaire, M. Chem. Rev.,  2005, 105(5), 1801-1836.
[http://dx.doi.org/10.1021/cr040652w] [PMID:  15884790] 
[27] 
Chen, Y.; Yekta, S.; Yudin, A.K. Chem. Rev.,  2003, 103(8), 3155-3212.
[http://dx.doi.org/10.1021/cr020025b] [PMID:  12914495] 
[28] 
Reuillard, B.; Ly, K.H.; Rosser, T.E.; Kuehnel, M.F.; Zebger, I.; Reisner, E. J. Am. Chem. Soc.,  2017, 139(41), 14425-14435.
[http://dx.doi.org/10.1021/jacs.7b06269] [PMID:  28885841] 
[29] 
Assalit, A.; Billard, T.; Chambert, S.; Langlois, B.R.; Queneau, Y.; Coe, D. Tetrahedron Asymmetry,  2009, 20, 593-601.
[http://dx.doi.org/10.1016/j.tetasy.2009.02.050] 
[30] 
Kitanosono, T.; Zhu, L.; Liu, C.; Xu, P.; Kobayashi, S. J. Am. Chem. Soc.,  2015, 137(49), 15422-15425.
[http://dx.doi.org/10.1021/jacs.5b11418] [PMID:  26646601] 
[31] 
Kanungo, B.K.; Baral, M.; Bhattacharya, S.; Sahoo, Y. Synth. Commun.,  2003, 33, 3159-3164.
[http://dx.doi.org/10.1081/SCC-120023436] 
[32] 
Yu, X.; Jin, X.; Tang, G.; Zhou, J.; Zhang, W.; Peng, D.; Hu, J.; Zhong, C. Eur. J. Org. Chem.,  2013, 5893-5901.
[http://dx.doi.org/10.1002/ejoc.201300192] 
[33] 
Ford, D.D.; Nielsen, L.P.; Zuend, S.J.; Musgrave, C.B.; Jacobsen, E.N. J. Am. Chem. Soc.,  2013, 135(41), 15595-15608.
[http://dx.doi.org/10.1021/ja408027p] [PMID:  24041239] 

Rights & Permissions Print Cite

Article Metrics

23

1

Journal Information

For Authors

For Editors

For Reviewers

Explore Articles

Open Access

Open Access Articles

For Visitors

DOI https://dx.doi.org/10.2174/1570178618666210706112141	Print ISSN 1570-1786
Publisher Name Bentham Science Publisher	Online ISSN 1875-6255

Letters in Organic Chemistry

The Efficient Synthesis of 2-(3-Carbamoylpyridine-2-yl) Nicotinamide Pyridine Salts

Abstract Play Pause

Graphical Abstract

Related Journals

Related Books

Abstract