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Synthesis and Acid Catalytic Activity of 1,5,3,7-Diazadiphosphocine-1,5-dicarboxylic Acids
Corresponding Author(s) : Dai Il Jung
Asian Journal of Chemistry,
Vol. 27 No. 4 (2015): Vol 27 Issue 4
Abstract
In order to synthesize new bioactive sompounds and contrasting agents, reactions of amino acids (glycine, aspartic acid and glutamic acid) with para formaldehyde and hypophosphorous acid were executed. Products are 3,7-dihydroxy-3,7-dioxoperhydro-1,5,3,7-diazadiphos-phocine-1,5-diacetic acid (4a), 2-[5-(1,2-dicarboxyethyl)-3,7-dihydroxy-3,7-dioxoperhydro-diazadiphosphocine-1-yl]-succinic acid (4b) and 3,7-dihydroxy-3,7-dioxoperhydro-1,5,3,7-diazadiphosphocine-1,5-di-(2-glutaric acid) (4c). As shown in Table-1, the reactions of 4a-c in presence of acid catalysts (all 100 % GC yields) gave only 8-phenyl-8-azabicyclo[3.2.1]octan-3-one (5) (4a; pH (1M) = 0.17, 4b; pH (1M) = 0.15, 4c; pH (1M) = 0.16). In case of inorganic acid catalysts, 8-phenyl-8-azabicyclo[3.2.1]octan-3-one (5) and N-phenyl pyrrole (6) (HCl: 5 = 89.4 and 6 = 10.3 %, H2SO4; 5 = 94.4 and 6 = 5.5 %, CH3COOH: 5 = 13 and 6 = 7.8 %, citric acid: 5 = 80.6 and 6 = 18.7 %) were synthesized. Because of selective acid catalytic ability of 4a-c, we will try reactivity studies as acid catalysts of 4a-c about all acid catalytic reactions.
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- P.A. Rink, Magnetic Resonance in medicine; Black Well Scientific Publications: Oxford, UK (1993).
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- S.K. Choi, K.M. Bang, J.H. Song, D.H. Lee, I.S. Kim, D.I. Jung and J.T. Hahn, Asian J. Chem., 22, 3094 (2010); P. Caravan, J.J. Ellison, T.J. McMurry and R.B. Lauffer, Chem. Rev., 99, 2293 (1999); doi:10.1021/cr980440x; W.A. Volkert and T.J. Hoffman, Chem. Rev., 99, 2269 (1999); doi:10.1021/cr9804386; M.H.V. Werts, R.H. Woudenberg, P.G. Emmerink, R. van Gassel, J.W. Hofstraat and J.W. Verhoeven, Angew. Chem., 39, 4542 (2000); doi:10.1002/1521-3773(20001215)39:24<4542::AID-ANIE4542>3.0.CO;2-C; I.F. Pickersgill and H. Rapoport, Org. Chem., 65, 4048 (2000); doi:10.1021/jo000071g; J.A.K. Howard, A.M. Kenwright, J.M. Moloney, D. Parker, M. Woods, J.A.K. Howard, M. Port, M. Navet and O. Rousseau, Chem. Commun., 1381 (1998); doi:10.1039/a802847h; S. Aime, M. Botta, M. Fasano, S.G. Crich and E. Terreno, J. Biol. Inorg. Chem., 1, 312 (1996); doi:10.1007/s007750050059; L.J.M. Kroft and A. de Roos, J. Magn. Reson. Imaging, 10, 395 (1999); doi:10.1002/(SICI)1522-2586(199909)10:3<395::AID-JMRI22>3.0.CO;2-P; A. Bogdanov, Adv. Drug Deliv. Rev., 37, 279 (1999); doi:10.1016/S0169-409X(98)00098-2.
References
P.A. Rink, Magnetic Resonance in medicine; Black Well Scientific Publications: Oxford, UK (1993).
A.E. Merbach and E. Toth, The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging; John Wiley & Sons Ltd: Chichester, UK (2001).
P. Caravan, J.J. Ellison, T.J. McMurry and R.B. Lauffer, Chem. Rev., 99, 2293 (1999); doi:10.1021/cr980440x.
I. Lukes, J. Kotek, P. Vojtisek and P. Hermann, Coord. Chem. Rev., 216-217, 287 (2001); doi:10.1016/S0010-8545(01)00336-8.
(a) S. Aime, M. Botta, S.G. Crich, G.B. Giovenzana, R. Pagliarin, M. Piccinini, M. Sisti and E. Terreno, J. Biol. Inorg. Chem., 2, 470 (1997); doi:10.1007/s007750050158; (b) S. Aime, M. Botta, L. Frullano, S. Geninatti Crich, G. Giovenzana, R. Pagliarin, G. Palmisano, F.R. Sirtori and M. Sisti, J. Med. Chem., 43, 4017 (2000); doi:10.1021/jm000983a.
B. Song, T. Storr, S. Liu and C. Orvig, Inorg. Chem., 41, 685 (2002); doi:10.1021/ic010716a.
S.K. Choi, K.M. Bang, J.H. Song, D.H. Lee, I.S. Kim, D.I. Jung and J.T. Hahn, Asian J. Chem., 22, 3094 (2010); P. Caravan, J.J. Ellison, T.J. McMurry and R.B. Lauffer, Chem. Rev., 99, 2293 (1999); doi:10.1021/cr980440x; W.A. Volkert and T.J. Hoffman, Chem. Rev., 99, 2269 (1999); doi:10.1021/cr9804386; M.H.V. Werts, R.H. Woudenberg, P.G. Emmerink, R. van Gassel, J.W. Hofstraat and J.W. Verhoeven, Angew. Chem., 39, 4542 (2000); doi:10.1002/1521-3773(20001215)39:24<4542::AID-ANIE4542>3.0.CO;2-C; I.F. Pickersgill and H. Rapoport, Org. Chem., 65, 4048 (2000); doi:10.1021/jo000071g; J.A.K. Howard, A.M. Kenwright, J.M. Moloney, D. Parker, M. Woods, J.A.K. Howard, M. Port, M. Navet and O. Rousseau, Chem. Commun., 1381 (1998); doi:10.1039/a802847h; S. Aime, M. Botta, M. Fasano, S.G. Crich and E. Terreno, J. Biol. Inorg. Chem., 1, 312 (1996); doi:10.1007/s007750050059; L.J.M. Kroft and A. de Roos, J. Magn. Reson. Imaging, 10, 395 (1999); doi:10.1002/(SICI)1522-2586(199909)10:3<395::AID-JMRI22>3.0.CO;2-P; A. Bogdanov, Adv. Drug Deliv. Rev., 37, 279 (1999); doi:10.1016/S0169-409X(98)00098-2.