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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

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

Author(s): Lei-Yang Zhang, Jing-Bo Geng, Nai-Xing Wang*, Yue-Hua Wu, Zhan Yan, Bao-Cai Xu* and Yalan Xing*

Volume 19, Issue 1, 2022

Published on: 06 July, 2021

Page: [41 - 45] Pages: 5

DOI: 10.2174/1570178618666210706112141

Price: $65

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.

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[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]

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