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Synthesis of Pyrrole by 1,5,3,7-Diazadiphosphocine-1,5-Dicarboxylic Acid as Acid Catalyst
Corresponding Author(s) : D.I. Jung
Asian Journal of Chemistry,
Vol. 27 No. 6 (2015): Vol 27 Issue 6
Abstract
As a part of research program related to the synthetic study of pharmacologically interesting compounds and good chelating agent for transition metal ion, we here report the synthesis of an unusual medium-sized ring heterocyclic ligand with mixed carboxylic-amino-phosphonic donating group. We have synthesized 3,7-dihydroxy-3,7-dioxoperhydro-1,5,3,7-diazadiphosphocine-1,5-diacetic acid (1a), 2-[5-(1,2-dicarboxyethyl-3,7-dihydroxy-3,7-dioxo-3[1,5,3,7]diazadiphosphocan-1-yl)-succinic acid (1b) and 3,7-dihydroxy-3,7-diox-operhydro-1,3,5,7-diazadiphosphocine-1,5-di-(2-glutaric acid) (1c). In order to analyze reactivity of synthesized dicarboxylic acids 1a-c as acid catalysts, we tried reactions of pyrrole formation according to acid variation. We know that the catalytic ability of synthesized dicarboxylic acids (1a-c) are very good at pyrrole formation reaction.
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- P. Caravan, J.J. Ellison, T.J. McMurry and R.B. Lauffer, Chem. Rev., 99, 2293 (1999); doi:10.1021/cr980440x.
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References
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. Int. Ed., 39, 4542 (2000); doi:10.1002/1521-3773(20001215)39:24<4542::AID-ANIE4542>3.0.CO;2-C.
I.F. Pickersgill and H.J. 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.A. Bogdanov Jr., M. Lewin and R. Weissleder, Adv. Drug Deliv. Rev., 37, 279 (1999); doi:10.1016/S0169-409X(98)00098-2.
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).
T. Viswanathan and W.L. Alworth, J. Med. Chem., 24, 822 (1981); doi:10.1021/jm00139a011.