Amination of Malononitrile Dimer to Amidines: Synthesis of 6‐aminopyrimidines

作者: N. A. A. Elkanzi , Ashraf A. Aly , Ahmed M. Shawky , Essmat M. El-Sheref , Nesrin M. Morsy

DOI: 10.1002/JHET.2510

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摘要: Reactions of amidines with malononitrile dimer in DMF and catalyzed piperidine are reported. The reaction occurred via amination process followed by cyclization to give racemic 6-aminopyrimidine compounds. mechanism was discussed. structure products elucidated mass spectrometry, IR NMR spectra together elemental analyses.

参考文章(24)
Jean-Albert Gautier, Marcel Miocque, Claude Combet Farnoux, Preparation and synthetic uses of amidines Amidines and Imidates: Volume 1 (1975). pp. 283- 348 ,(2010) , 10.1002/9780470771495.CH7
Romeo Romagnoli, Pier Giovanni Baraldi, Vincent Remusat, Maria Dora Carrion, Carlota Lopez Cara, Delia Preti, Francesca Fruttarolo, Maria Giovanna Pavani, Mojgan Aghazadeh Tabrizi, Manlio Tolomeo, Stefania Grimaudo, Jan Balzarini, Mary Ann Jordan, Ernest Hamel, Synthesis and biological evaluation of 2-(3',4',5'-trimethoxybenzoyl)-3-amino 5-aryl thiophenes as a new class of tubulin inhibitors. Journal of Medicinal Chemistry. ,vol. 49, pp. 6425- 6428 ,(2006) , 10.1021/JM060804A
Rolf Paul, William A. Hallett, John W. Hanifin, Marvin F. Reich, Bernard D. Johnson, Robert H. Lenhard, John P. Dusza, Suresh S. Kerwar, Yang I Lin, Preparation of substituted N-phenyl-4-aryl-2-pyrimidinamines as mediator release inhibitors. Journal of Medicinal Chemistry. ,vol. 36, pp. 2716- 2725 ,(1993) , 10.1021/JM00071A002
Olivier Neus, Dany Callens, Robert Bulcke, Soil Metabolism of the Herbicide Rimsulfuron under Laboratory and Field Conditions Journal of Agricultural and Food Chemistry. ,vol. 45, pp. 3283- 3291 ,(1997) , 10.1021/JF9606161
Laura Wing, Heather Behanna, Linda Van Eldik, D. Martin Watterson, Hantamalala Ralay Ranaivo, De novo and molecular target-independent discovery of orally bioavailable lead compounds for neurological disorders. Current Alzheimer Research. ,vol. 3, pp. 205- 214 ,(2006) , 10.2174/156720506777632844
Vladimir G Granik, Advances in the Chemistry of Amidines Russian Chemical Reviews. ,vol. 52, pp. 377- 393 ,(1983) , 10.1070/RC1983V052N04ABEH002824
David Moffat, Peter Davis, Martin Hutchings, Jeremy Davis, Daniel Berg, Mark Batchelor, James Johnson, James O'Connell, Richard Martin, Tom Carabbe, Jean Delgado, Martin Perry, 4-Pyridin-5-yl-2-(3,4,5-trimethoxyphenylamino)pyrimidines: Potent and selective inhibitors of ZAP 70 Bioorganic & Medicinal Chemistry Letters. ,vol. 9, pp. 3351- 3356 ,(1999) , 10.1016/S0960-894X(99)00615-0
Jürg Zimmermann, Elisabeth Buchdunger, Helmut Mett, Thomas Meyer, Nicholas B. Lydon, Peter Traxler, Phenylamino-pyrimidine (PAP) — derivatives: a new class of potent and highly selective PDGF-receptor autophosphorylation inhibitors Bioorganic & Medicinal Chemistry Letters. ,vol. 6, pp. 1221- 1226 ,(1996) , 10.1016/0960-894X(96)00197-7
Zhili Xin, Michael D. Serby, Hongyu Zhao, Christi Kosogof, Bruce G. Szczepankiewicz, Mei Liu, Charles W. Hutchins, Kathy A. Sarris, Ethan D. Hoff, H. Douglas Falls, Chun W. Lin, Christopher A. Ogiela, Christine A. Collins, Michael E. Brune, Eugene N. Bush, Brian A. Droz, Thomas A. Fey, Victoria E. Knourek-Segel, Robin Shapiro, Peer B. Jacobson, David W. A. Beno, Teresa M. Turner, Hing L. Sham, Gang Liu, Discovery and pharmacological evaluation of growth hormone secretagogue receptor antagonists. Journal of Medicinal Chemistry. ,vol. 49, pp. 4459- 4469 ,(2006) , 10.1021/JM060461G
Hongyu Zhao, Michael D. Serby, Zhili Xin, Bruce G. Szczepankiewicz, Mei Liu, Christi Kosogof, Bo Liu, Lissa T. J. Nelson, Eric F. Johnson, Sanyi Wang, Terry Pederson, Rebecca J. Gum, Jill E. Clampit, Deanna L. Haasch, Cele Abad-Zapatero, Elizabeth H. Fry, Cristina Rondinone, James M. Trevillyan, Hing L. Sham, Gang Liu, Discovery of potent, highly selective, and orally bioavailable pyridine carboxamide c-Jun NH2-terminal kinase inhibitors. Journal of Medicinal Chemistry. ,vol. 49, pp. 4455- 4458 ,(2006) , 10.1021/JM060465L