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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Letter Article

Efficient Route for Synthesis of Enamines from 1,3-Alkyl-2-Thioxodihydropyrimidine-4,6(1H,5H)-dione Enols

Author(s): Anamika Sharma, Zainab M. Almarhoon, Ayman El-Faham*, Beatriz G. de la Torre* and Fernando Albericio*

Volume 16, Issue 7, 2019

Page: [538 - 540] Pages: 3

DOI: 10.2174/1570178616666190409145118

Price: $65

Abstract

Here we report a greener approach for the synthesis of enamines from enols of 1,3-alkyl-2- thioxodihydropyrimidine-4,6(1H,5H)-dione (thiobarbituric acid) acid using ammonium chloride and ethanol as solvents. This protocol removes the need for catalysts or harsh conditions.

Keywords: Thiobarbituric acid, enols, enamines, greener approach, ammonium chloride, HPLC.

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[1]
Xie, J-H.; Zhu, S-F.; Zhou, Q-L. Chem. Soc. Rev., 2012, 41(11), 4126-4139.
[2]
Kempf, B.; Hampel, N.; Ofial, A.R.; Mayr, H. Chem. Eur. J., 2003, 9(10), 2209-2218.
[3]
Wittig, G.; Blumenthal, H. Ber. Dtsch. Chem. Ges., 1927, 60(5), 1085-1094.
[4]
Charushin, V.N.; Mochulskaya, N.N.; Andreiko, A.A.; Filyakova, V.I.; Kodess, M.I.; Chupakhin, O.N. Tetrahedron Lett., 2003, 44(11), 2421-2424.
[5]
Savarin, C.G.; Murry, J.A.; Dormer, P.G. Org. Lett., 2002, 4(12), 2071-2074.
[6]
Eddington, N.D.; Cox, D.S.; Khurana, M.; Salama, N.N.; Stables, J.P.; Harrison, S.J.; Negussie, A.; Taylor, R.S.; Tran, U.Q.; Moore, J.A. Eur. J. Med. Chem., 2003, 38, 49-64.
[7]
Dannhardt, G.; Bauer, A.; Nowe, U. J. Prakt. Chem. Chem. Ztg., 1998, 340(3), 256-263.
[8]
Boger, D.L.; Ishizaki, T.; Wysocki, Jr, R.J.; Munk, S.A.; Kitos, P.A.; Suntornwat, O. J. Am. Chem. Soc., 1989, 111(16), 6461-6463.
[9]
Xie, J-H.; Zhu, S-F.; Zhou, Q-L. Chem. Rev., 2010, 111(3), 1713-1760.
[10]
Borrmann, R.; Koenigs, R.M.; Zoller, J.; Rueping, M. Synthesis, 2017, 49(2), 310-318.
[11]
Dehli, J.R.; Legros, J.; Bolm, C. Chem. Commun., 2005, 8, 973-986.
[12]
Yang, Y-D.; Azuma, A.; Tokunaga, E.; Yamasaki, M.; Shiro, M.; Shibata, N. J. Am. Chem. Soc., 2013, 135(24), 8782-8785.
[13]
Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc., 1963, 85(2), 207-222.
[14]
Westheimer, F.; Taguchi, K. J. Org. Chem., 1971, 36(11), 1570-1572.
[15]
White, W.A.; Weingarten, H. J. Org. Chem., 1967, 32(1), 213-214.
[16]
Pommier, J-C.; Roubineau, A. J. Organomet. Chem., 1973, 50(1), 101-111.
[17]
Yamamoto, Y.; Matui, C. J. Org. Chem., 1998, 63(2), 377-378.
[18]
Gholap, A.R.; Chakor, N.S.; Daniel, T.; Lahoti, R.J.; Srinivasan, K.V. J. Mol. Catal. A: Chem., 2006, 245(1-2), 37-46.
[19]
Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C.G.; Seayad, J.; Thiel, O.R.; Tillack, A.; Trauthwein, H. Synlett, 2002, 2002(10), 1579-1594.
[20]
Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem. Int. Ed., 2004, 43(26), 3368-3398.
[21]
Petasis, N.A.; Lu, S-P. Tetrahedron Lett., 1995, 36(14), 2393-2396.
[22]
Patmore, E.L.; Chafetz, H. J. Org. Chem., 1967, 32(4), 1254-1255.
[23]
Tanaka, K.; Toda, F. Chem. Rev., 2000, 100(3), 1025-1074.
[24]
Metzger, J.O. Angew. Chem. Int. Ed., 1998, 37(21), 2975-2978.
[25]
Ji, Z.; Ahmed, A.A.; Albert, D.H.; Bouska, J.J.; Bousquet, P.F.; Cunha, G.A.; Glaser, K.B.; Guo, J.; Li, J.; Marcotte, P.A. Bioorg. Med. Chem. Lett., 2006, 16(16), 4326-4330.
[26]
Banerjee, A.; Yadav, P.S.; Bajpai, M.; Sangana, R.R.; Gullapalli, S.; Gudi, G.S.; Gharat, L.A. Bioorg. Med. Chem. Lett., 2012, 22(9), 3223-3228.
[27]
Erker, G.; Pfaff, R.; Kowalski, D.; Wuerthwein, E.U.; Krueger, C.; Goddard, R. J. Org. Chem., 1993, 58(24), 6771-6778.
[28]
Sharma, A.; Noki, S.; Zamisa, S.J.; Hazzah, H.A.; Almarhoon, Z.M.; El‐Faham, A.; de la Torre, B.G.; Albericio, F. ChemMedChem, 2018, 13(18), 1923-1930.

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