Abstract
Aryl N-alkoxycarbamates labeled with carbon-14 have been synthesized from aryl nitrile-[cyano-14C] as part of a 2-step sequence. The resulted carbamates were treated with amines, generating [carbonyl-14C]-Ureas in high yield and purity.
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References
Matsuda, K.: ACAT inhibitors as antiatherosclerotic agents: compounds and mechanisms. Med. Res. Rev. 14, 271–305 (1994)
Saljoughian, M., Morimoto, H., Williams, P.G., Than, C., Seligman, S.J.: N-Tritioacetoxyphthalimide: a new high specific activity tritioacetylating reagent. J. Org. Chem. 61, 9625–9628 (1996)
Saemian, N., Shirvani, G., Matloubi, H.: Synthesis of 1–(4- methylsulfone–phenyl)-5-(4-fluoro–phenyl)-5-[14C]-1,2,3-triazole and 1–(4-sulfonamide-phenyl)-5-(4-fluoro-phenyl)-5-[14C]-1,2,3-triazole as novel carbon-14 anticonvulsant. J. Radioanal. Nuc. Chem. 268, 545–548 (2006)
Matloubi, H., Ghandi, M., Saemian, N.: Synthesis of a carbon-14 analogue of 8-chloro-11-(4-methyl-1-piperazinyl)-11-[14C]-dibenzo[b,f][1,4]oxazepine. Appl. Radiat. Isot. 57, 501–504 (2002)
Matloubi, H., Khalaj, A., Dowlatabadi, R., Shirvani, G.: Synthesis of N-(2,3-dihydro-1-[14C]methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-yl)benzamide and N-(2,3-dihydro-1-[14C]methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-yl)-N-[14C]methyl-benzamide as novel carbon-14 labelled CCK antagonists. J. Label. Compd. Radiopharm. 45, 347–350 (2002)
Sunay, U.B., Talbot, K.C., Galullo, V.: Synthesis of carbon-14 and tritium labelled analogs of the novel antischizophrenic agent clozapine. J. Label. Compd. Radio Pharm. 31, 1041–1047 (1992)
Perry, C.W., Burger, W., Dlaney, C.M.: An improved of preparation of potassium [14C] cyanide. J. Label. Compd. Radiopharm. 16, 645–649 (1978)
Saemian, N., Shirvani, G., Matloubi, H.: Synthesis of 14C analogue of 1,2-diaryl-[2-14C]-pyrroles. J. Radioanal. Nuc. Chem. 274, 631–634 (2007)
Matloubi, H., Ghandi, M., Zarrindast, M.R., Saemian, N.: Modifide synthesis of 11-[14C] clozapine. Appl. Radiat. Isot. 55, 789–791 (2001)
Seidel, D., Brehmer, P., Schoof, Y., Weinberg, U., Niewohner, U., Nowakowski, M.: Synthesis of [14C]-labelled vardenafil hydrochloride and methbolites. J. Label. Compd. Radiopharm. 46, 1019–1032 (2003)
Manning, C.O., Wadsworth, A.H., Fellows, I.: Synthesis of stable isotopically labeled versions of iamotrigine and its methylated metabolite. J. Label. Compd. Radiopharm. 45, 611–618 (2002)
Saemian, N., Shirvani, G., Matloubi, H.: Synthesis of carbon-14 analogue of N-(1-Methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)-benzamide-[carboxy-14C] as CCK-A antagonist. J. Labelled Cpd. Radiopharm. 49, 71–76 (2006)
Saemian, N., Shirvani, G., Matloubi, H.: A convenient method for synthesis of 11-[14C]-loxapine. Nukleonika 50, 139–141 (2005)
Keillor, J.W., Huang, X., Seid, M.: A mild and efficient modified Hofmann rearrangement. J. Org. Chem. 62, 7495–7496 (1997)
Thavonekham, B.: A practical synthesis of ureas from phenyl carbamates. Synthesis (1997) 1189–1194
Acknowledgments
We gratefuly acknowledge the help of Dr. R. Dowlatabadi (Tehran University of Medical Science, Faculty of Pharmacy) and Mr. N. Ali-Reza Zadeh (AEOI) for 1H-NMR spectroscopy and radioactivity determination of synthesized samples, respectively.
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Saemian, N., Shirvani, G. & Javaheri, M. Synthesis of a carbon-14 analogue of aryl N-alkoxycarbamates and its application for synthesis of unsymmetrical N,N′-urea derivatives. J Radioanal Nucl Chem 281, 421–423 (2009). https://doi.org/10.1007/s10967-009-0005-y
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DOI: https://doi.org/10.1007/s10967-009-0005-y