Advanced SearchSearch Tips
One-pot Four Component Reaction of Unsymmetrical 1-Methylbarbituric Acid with BrCN and Various Aldehydes in the Presence of Et3N and/or Pyridine
facebook(new window)  Pirnt(new window) E-mail(new window) Excel Download
 Title & Authors
One-pot Four Component Reaction of Unsymmetrical 1-Methylbarbituric Acid with BrCN and Various Aldehydes in the Presence of Et3N and/or Pyridine
Jalilzadeh, Mohammad; Pesyan, Nader Noroozi;
  PDF(new window)
Reaction of 1-methylpyrimidine-(1H,3H,5H)-2,4,6-trione (1-MBA 1) as an unsymmetrical barbituric acid with cyanogen bromide and various aldehydes in the presence of triethylamine and/or pyridine afforded diastereomeric mixtures of new class of heterocyclic stable 5-aryl-1,1`-dimethyl- and 5-aryl-3,1`-dimethyl-1H,1`H-spiro[furo[2,3-d]pyrimidine-6,5`-pyrimidine]2,2`,4,4`,6`(3H,3`H,5H)-pentaones which are dimeric forms of 1-methyl barbiturate at the range of to room temperature. In the reaction of some aldehydes with 1-MBA and BrCN were afforded a mixture of diastereomers. Another two aldehydes such as 4-cyano- and 2-hydroxybenzaldehydes gave exclusively two diastereomers in which binded to the salt of triethylammonium hydrobromide by intermolecular H-bond in ratio of 1:1. 4-Hydroxybenzaldehyde and 2-pyridinecarbaldehyde gave exclusively one diastereomer under the same condition. Aldehydes possessing strong electron-donor were produced exclusively two geometric isomers of Knoevenagel adduct (E- and Z-isomers). The structures of compounds were deduced by NMR, NMR and FT-IR spectroscopy. Mechanism of the formation is discussed.
1-Methyl barbituric acid;Spiro barbiturate;Biological effect;Cyanogen bromide;Diastereomer;
 Cited by
Unique charge-separated intermolecular and eight-membered intramolecular H-bonds in bis-(thio)barbiturates, Journal of the Iranian Chemical Society, 2014, 11, 1, 35  crossref(new windwow)
Solvent-free, one-pot synthesis of pentasubstituted cyclopropanes in the presence of BrCN and EtONa by milling, Monatshefte für Chemie - Chemical Monthly, 2014, 145, 7, 1165  crossref(new windwow)
New synthetic protocol for stereoselective synthesis of diethyl 1,2-dicyano-3-alkyl-(aryl)cyclopropane-1,2-dicarboxylate, Journal of the Iranian Chemical Society, 2015, 12, 7, 1261  crossref(new windwow)
A New, Fast and Easy Strategy for One-pot Synthesis of Full Substituted Cyclopropanes: Direct Transformation of Aldehydes to 3-Aryl-1,1,2,2-tetracyanocyclopropanes, Journal of the Chinese Chemical Society, 2013, 60, 1, 35  crossref(new windwow)
Synthesis of Bis-spiro Cyclopropanes Based on Meldrum’s Acid by Milling, Journal of the Chinese Chemical Society, 2015, 62, 3, 249  crossref(new windwow)
Regioselective One-pot Synthesis of New Unsymmetric Spiro Dihydrofurans in the Reaction of Mixed Two Different Cyclic β-Dicarbonyl Compounds with BrCN and Aldehydes in the Presence of Et3N, Journal of the Chinese Chemical Society, 2015, 62, 3, 234  crossref(new windwow)
Cody, V.; Galitsky, N.; Luft, JR.; Pangborn, W.; Gangjee, A.; Devraj, R.; Queener, S. F.; Blakley, R. L. Acta Crystallogr., Sect. D 1997, 53, 638. crossref(new window)

Melik-Ogandzhanyan, R. G.; Khachatryan, V. E.; Gapoyan, A. S. Russ. Chem. Rev. 1985, 54, 262. crossref(new window)

Figueroa-Villar, J. D.; Carneiro, C. L.; Cruz, E. R. Heterocycles 1992, 34, 891. crossref(new window)

Campaigne, E.; Ellis, R. L.; Bradford, M.; Ho, J. J. Med. Chem. 1969, 12, 339. crossref(new window)

Blume, F.; Arndt, F.; Ress, R. Ger. Patent, 3712782, 1988.

Krasnov, K.; Kartsev, V. Russ. J. Org. Chem. 2005, 41, 901. crossref(new window)

Kotha, S.; Deb, A. C.; Kumar, R. V. Bioorg. Med. Chem. Lett. 2005, 15, 1039. crossref(new window)

Gerkens, J. F. Eur. J. Pharmacol. 1987, 134, 293. crossref(new window)

Duan, J.; Lu, Z. US Patent 6 936 620 B2, 2005.

Brown, D. J. Comprehensive heterocyclic chemistry; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon, Oxford: 1984; Vol. 3.

Wamhoff, H.; Dzenis, J.; Hirota, K. Adv. Heterocycl. Chem. 1992, 55, 129. crossref(new window)

Naya, S. I.; Miyama, H.; Yasu, K.; Takayasu, T.; Nitta, M. Tetrahedron 2003, 59, 1811. crossref(new window)

Capella-Peiro, M.-E.; Carda-Broch, S.; Monferrer-Pons, L.; Esteve-Romero, J. Anal. Chim. Acta 2004, 517, 81. crossref(new window)

Pelletier, O.; Campbell, J. A. J. Pharm. Sci. 1962, 51, 594. crossref(new window)

Pelletier, O.; Campbell, J. A. J. Pharm. Sci. 1961, 50, 926. crossref(new window)

Jursic, B. S.; Stevens, E. D. Tetrahedron Lett. 2003, 44, 2203. crossref(new window)

Moskvin, A. V.; Reznikova, N. R.; Ivin, B. A. Russ. J. Org. Chem. 2002, 38, 463. crossref(new window)

Jursic, B. S.; Douelle, F.; Stevens, E. D. Tetrahedron 2003, 59, 3427. crossref(new window)

Spange, S.; Bauer, M.; Walfort, B.; Lang, H. J. Org. Chem. 2006, 71, 7850. crossref(new window)

Jursic, B. S.; Neumann, D. M.; Martin, K. L.; Stevens, E. D. Org. Lett. 2002, 4, 811. crossref(new window)

Jursic, B. S.; Neumann, D. M.; Moore, Z.; Stevens, E. D. J. Org. Chem. 2002, 67, 2372. crossref(new window)

McClenaghan, N. D.; Absalon, C.; Bassani, D. M. J. Am. Chem. Soc. 2003, 125, 13004. crossref(new window)

Renard, A.; Lhomme, J.; Kotera, M. J. Org. Chem. 2002, 67, 1302. crossref(new window)

Paramonov, I. V.; Belyaev, N. A.; Glukhareva, T. V.; Volkov, A. S.; Deeva, E. V. Chem. Heterocycl. Compd. 2006, 42, 127. crossref(new window)

Naya, S.-I.; Yoda, K.; Nitta, M. Tetrahedron 2005, 61, 8616. crossref(new window)

Kumar, V. Synlett 2005, 10, 1638.

Martin, D.; Bauer, M. Cyanic acid estersfrom phenols: phenyl cyanate; Org. Synth. Coll.: 1990; Vol. 7, p 435.

Gross, E.; Witkop, B. J. Am. Chem. Soc. 1961, 83, 1510. crossref(new window)

McCallum, P. B. W.; Grimmett, M. R.; Blackman, A. G.; Weavers, R. T. Aust. J. Chem. 1999, 52, 159. crossref(new window)

Tanner, D. D.; Lycan, G.; Bunce, N. J. Can. J. Chem. 1970, 48, 1492. crossref(new window)

Alberola, A.; Andres, C.; Ortega, A. G.; Pedrosa, R.; Vicente, M. Synth Commun. 1986, 16, 1161. crossref(new window)

Jalilzadeh, M.; Noroozi Pesyan, N.; Rezaee, F.; Rastgar, S.; Hosseini, Y.; Sahin, E. Mol. Divers. 2011, 15, 721. crossref(new window)

Hosseini, Y.; Rastgar, S.; Heren, Z.; Buyukgungor, O.; Noroozi Pesyan, N. J. Chin. Chem. Soc. 2011, 58, 309. crossref(new window)

Noroozi Pesyan, N.; Rastgar, S.; Hosseini, Y. Acta Crystallogr., Sect. E 2009, 65, o1444. crossref(new window)

Brown, D. J.; Mason, S. F. Chemistry of Heterocyclic Compounds: The Pyrimidines; John Wiley & Sons: New York, 1962; Vol. 16.

Huang, C-H. McClenaghan, N. D.; Kuhn, A.; Bravic, G.; Bassani, D. M. Tetrahedron 2006, 62, 2050. crossref(new window)

Adamson, J.; Coe, B. J.; Grassam, H. L.; Jeffery, J. C.; Coles, S. J.; Hursthouse, M. B. J. Chem. Soc. Perkin Trans 1 1999, 2483.

Figueroa-Villar, J. D.; Cruz, E. R. Tetrahedron 1993, 49, 2855. crossref(new window)

Zhdanov, Y. A.; Bogdanova, G. V. Chem. Heterocycl. Compd. 1966, 2, 41.

Krasnov, K. A.; Kartsev, V. G.; Santarovich, E. E. Chem. Heterocycl. Compd. 2002, 38, 702. crossref(new window)

Zoorob, H. H.; Abou-El Zahab, M. M.; Abdel-Mogib, M.; Ismail, M. A. Tetrahedron 1996, 52, 10147. crossref(new window)

Ahluwalia, V. K.; Sharma, M. K.; Aggarwal, R.; Chauchan, A.; Sharma, R. Indian J. Chem., Sec. B 1991, 30, 598.

Kato, S.; Poling, M.; van der Helm, D.; Dryhurst, G. J. Am. Chem. Soc. 1974, 96, 5255. crossref(new window)

Kato, S.; Dryhurst, G. J. Electroanal. Chem. 1975, 62, 415. crossref(new window)

Poling, M.; van der Helm, D. Acta Crystallogr., Sect. B. 1976, 32, 3349. crossref(new window)

Horcajada, R.; Batanero, B.; Barba, F.; Martyin, A. Tetrahedron Lett. 2007, 48, 6437. crossref(new window)

Asiri, A. M.; Khan, S. A.; Ng, S. W. Acta Crystallogr., Sect. E 2009, 65, o1860. crossref(new window)

Vogel, A. Vogel's textbook of practical organic chemistry, 4th ed.; Longman: New York, 1978.

Hartman, W. W.; Dreger, E. E. Org. Synth. Coll., Vol. 2; 1943; p 150.