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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

A Practical Synthesis of Macrocyclic Schiff Base Bearing Hydroxyethyl Pendants Utilizing Solubility Discrepancies

Author(s): Runlai Li*, Shu’an Li, Tian Xia, Chunwei Ji, Na Gu, Linzhe Li and Zhenming Zhang*

Volume 19, Issue 9, 2022

Published on: 24 January, 2022

Page: [719 - 724] Pages: 6

DOI: 10.2174/1570178619666211230124256

Price: $65

Abstract

Six macrocyclic Schiff bases bearing hydroxyethyl pendants have been synthesized in high yields via [2 + 2] condensation between the rigid dialdehydes and 2-[bis(2-aminoethyl)amino]ethanol or 1-[bis(2-aminoethyl)amino]-2-propanol at 0°C for 12 hours in the CH3CN/H2O mixture. Solubility discrepancies between macrocyclic products and raw materials in selected solvents enable a facile separation and high yields, avoiding any intractable chromatographic purification. This straightforward synthetic protocol provides a relatively facile resolution with potential widespread applications for the synthesis of Schiff bases.

Keywords: Macrocyclic Schiff bases, pendants, [2+2] condensation, solubility discrepancies, macrocyclic synthesis, hydroxyethyl.

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[1]
Gull, P.; Hashmi, A.A. J. Braz. Chem. Soc., 2015, 26, 1331-1337.
[http://dx.doi.org/10.5935/0103-5053.20150099]
[2]
Fedorov, Y.V.; Fedorova, O.A.; Kalmykov, S.N.; Oshchepkov, M.S.; Nelubina, Y.V.; Arkhipov, D.E.; Egorova, B.V.; Zubenko, A.D. Polyhedron, 2017, 124, 229-236.
[http://dx.doi.org/10.1016/j.poly.2016.12.037]
[3]
López-Martínez, L.M.; Santacruz-Ortega, H.; Navarro, R.E.; Inoue, M.; Sugich-Miranda, R.; Hernández-Paredes, J.; Castillo, I.; Sotelo-Mundo, R.R. Polyhedron, 2017, 127, 438-448.
[http://dx.doi.org/10.1016/j.poly.2016.10.028]
[4]
Lehn, J.M. Acc. Chem. Res., 1978, 11, 49-57.
[http://dx.doi.org/10.1021/ar50122a001]
[5]
Kang, S-G.; Kim, M-S.; Kim, S-J.; Ryu, K. Polyhedron, 1996, 15, 1835-1840.
[http://dx.doi.org/10.1016/0277-5387(95)00431-9]
[6]
Rossignoli, M.; Bernhardt, P.V.; Lawrance, G.A.; Maeder, M. J. Chem. Soc., Dalton Trans., 1997, 323-328.
[http://dx.doi.org/10.1039/a606678j]
[7]
Wainwright, K.P. Adv. Inorg. Chem., 2001, 52, 293-334.
[http://dx.doi.org/10.1016/S0898-8838(05)52006-3]
[8]
Chen, D.; Martell, A.E. Tetrahedron, 1991, 47, 6895-6902.
[http://dx.doi.org/10.1016/S0040-4020(01)96145-9]
[9]
McKenzie, C.J.; Nielsen, L.P.; Srbtofteb, I. Acta Chem. Scand. A, 1998, 52, 571-577.
[http://dx.doi.org/10.3891/acta.chem.scand.52-0571]
[10]
Mikuriya, M.; Nakadera, K.; Tokii, T. Inorg. Chim. Acta, 1992, 194, 129-131.
[http://dx.doi.org/10.1016/S0020-1693(00)82653-5]
[11]
Shangguan, G.; Martell, A.E.; Zhang, Z.; Reibenspies, J.H. Inorg. Chim. Acta, 2000, 299, 47-58.
[http://dx.doi.org/10.1016/S0020-1693(99)00468-5]
[12]
Troadec, T.; Thompson, A.L.; Chaplin, A.B. Tetrahedron Lett., 2015, 56, 4613-4615.
[http://dx.doi.org/10.1016/j.tetlet.2015.05.110]
[13]
Santa María, D.; Claramunt, R.M.; Torralba, M.C.; Torres, M.R.; Elguero, J. Tetrahedron Lett., 2019, 60, 1206-1209.
[http://dx.doi.org/10.1016/j.tetlet.2019.03.066]
[14]
Li, S-A.; Xia, J.; Yang, D-X.; Xu, Y.; Li, D-F.; Wu, M-F.; Tang, W-X. Inorg. Chem., 2002, 41(7), 1807-1815.
[http://dx.doi.org/10.1021/ic011019l] [PMID: 11925173]
[15]
Lindoy, L.F.; Busch, D.H. J. Am. Chem. Soc., 1969, 91, 4690-4693.
[http://dx.doi.org/10.1021/ja01045a016]
[16]
Lindoy, L.F. The Chemistry of Macrocyclic Ligand Complexes; Cambridge University Press, 1990.
[17]
Pilkington, N.H.; Robson, R. Aust. J. Chem., 1970, 23, 2225-2236.
[18]
Cong, H.; Ni, X.L.; Xiao, X.; Huang, Y.; Zhu, Q-J.; Xue, S-F.; Tao, Z.; Lindoy, L.F.; Wei, G. Org. Biomol. Chem., 2016, 14(19), 4335-4364.
[http://dx.doi.org/10.1039/C6OB00268D] [PMID: 26991738]
[19]
Lindsay-Scott, P.J.; Barlow, H. Synlett, 2016, 27, 1516-1520.
[http://dx.doi.org/10.1055/s-0035-1561395]
[20]
Hobbs, D.M.; Schubert, P.; Tung, H-H. Ind. Eng. Chem. Res., 1997, 36, 5302-5306.
[http://dx.doi.org/10.1021/ie970438g]
[21]
Li, S-A.; Li, D-F.; Yang, D-X.; Li, Y.Z.; Huang, J.; Yu, K.B.; Tang, W-X. Chem. Commun. (Camb.), 2003, (7), 880-881.
[http://dx.doi.org/10.1039/b300013c] [PMID: 12739658]
[22]
Huang, J.; Li, S-A.; Li, D-F.; Yang, D-X.; Sun, W-Y.; Tang, W-X. Bioorg. Med. Chem., 2004, 12(3), 529-535.
[http://dx.doi.org/10.1016/j.bmc.2003.11.020] [PMID: 14738961]
[23]
Agrahari, A.K.; Jaiswal, M.K.; Yadav, M.S.; Tiwari, V.K. Carbohydr. Res., 2021, 508, 108403.
[http://dx.doi.org/10.1016/j.carres.2021.108403] [PMID: 34329845]

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