Oxidative Dehydrogenation of 4-Arylurazoles

Oxidative Dehydrogenation of 4-Arylurazoles Russian Journal of Applied Chemistry, Vol. 75, No. 2, 2002, p. 332. Translated from Zhurnal Prikladnoi Khimii, Vol. 75, No. 2, 2002, p. 342. Original Russian Text Copyright C 2002 by Wamhoff, Zlotskii, Saprygina. BRIEF ˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝ ˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝ COMMUNICATIONS H. Wamhoff, S. S. Zlotskii, and V. A. Saprygina Kekulé Institut fu 1r Organische Chemie und Biochemie der Universitat 1 Bonn, Bonn, Germany Ufa State of University of Petroleum Engineering, Ufa, Bashkortostan, Russia Reaktiv Research Institute, Ufa, Bashkortostan, Russia Received July 9, 2001 Abstract-4-Arylurazoles are selectively oxidized with Fe (NO ) . 9H O to the corresponding D -1,2,4-tri- 2 3 3 2 azoline-3,5-diones. Recently there has been growing interest inD -1,2,4- HCl was added to pH < 2, and the resulting bright red triazoline-3,5-diones, which are extremely active di- liquid was diluted with an equal volume of ice-cold enophiles and are successfully used in syntheses of water. The precipitate was filtered off, washed with fused and polysubstituted heterocycles [133]. Also, water, and vacuum-dried. Target compounds IIa3IIc these compounds react with olefins to form the cor- were obtained in 65 375% yields; their constants responding secondary amines [4, 5]. The most ver- agreed with published data [9, 10]. satile and widely used route to D -1,2,4-triazoline-3,5- ACKNOWLEDGMENTS diones is oxidation of the corresponding urazoles (1,2,4-triazolidine-3,5-diones). The study was performed within the framework Along with the use of powerful oxidants, such as of the Academic Exchange Program of the German tert-butyl hypochlorite [6], trichloroacetyl isocyanate Academy (DAAD), grant A/99/09 940. [7], or nitrogen dioxide [8], procedures have been developed for oxidation with N-bromosuccinimide REFERENCES [9, 10] and halogens [11]: 1. The Chemistry of Heterocyclic Compounds, Mont- O O i i i i gomery, J.A., Ed., New York: Wiley, 1981, vol. 37. NH 3C N 3C f [O] f g g g c c 2. Adam, W. and Lucchi, O. de, Angew. Chem., 1980, N R N R, g g g g g g vol. 92, no. 10, pp. 815 3 832. h h NH 3C N 3C e e 3. Wagner, Th.J., Synthesis, 1980, no. 7, pp. 165 3214, e e O O 769 3798. Ia3Ic IIa3IIc 4. Adam, W., Pastor, A., and Wirth, T., Org. Lett., 2000, vol. 5, pp. 1295 31297. where R = Ph (a), 4-ClC H (b), 3,4-Cl C H (c). 6 4 2 6 3 5. Vassilikogiannakis, G., Stratakis, V., Orfanopoulus, M., In addition to the known procedures, we found that and Foote, C.S.D., J. Org. Chem., 1999, vol. 64?, 4-arylurazoles Ia3Ic can be oxidized to 4-aryl-D -1,2,4- no. 11, pp. 4130 3 4139. triazoline-3,5-diones IIa3IIc with iron(III) nitrate un- 6. Cookson, R.C., Gupte, S.S., Stevens, J.D.R., and der mild conditions in high yields (65 375%). The re- Watts, C.T., Org. Synth., 1971, vol. 51, pp. 1213127. action occurs in the solid phase, which considerably 7. Moore, J.A., Muth, R., and Sorace, R., J. Org. Chem., simplifies the isolation and purification of the target 1974?, vol. 39, no. 25, pp. 3799 33800. diones IIa3IIc. A similar procedure has been used 8. Stickler, J.C. and Pirkle, W.H., J. Org. Chem., 1966, previously to prepare substituted semicarbazides [12]. vol. 31, no. 10, pp. 3444 33445. 9. Wamhoff, H. and Wald, K., Org. Prep. Proced. Int., EXPERIMENTAL 1975, vol. 7, pp. 2513253. 10. Fieser M. and Fieser, L.F., Reagents of Organic Syn- 4-Aryl- D -1,2,4-triazoline-3,5-diones IIa 3IIc. thesis, New York: Wiley, 1977, vol. 6. A mixture of triazolidinedione Ia3Ic with Fe (NO ) . 11. Wamhoff, H. and Kunz, G., Angew. Chem., 1981, 2 3 3 9H O (molar ratio 1 : 2) was ground in an agate mor- vol. 93, no. 9, pp. 8323833. tar for 53 8 min. The mixture was transferred into dry 12. Wang, C., Wang, J., and Li, J., Synth. Commun., 1999, acetone (15 ml per millimole of Ia3Ic), concentrated vol. 29, no. 15, pp. 2597 32599. 1070-4272/02/7502-0332 $27.00 C 2002 MAIK [Nauka/Interperiodica] http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Russian Journal of Applied Chemistry Springer Journals

Oxidative Dehydrogenation of 4-Arylurazoles

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Chemistry; Chemistry/Food Science, general
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Abstract

Russian Journal of Applied Chemistry, Vol. 75, No. 2, 2002, p. 332. Translated from Zhurnal Prikladnoi Khimii, Vol. 75, No. 2, 2002, p. 342. Original Russian Text Copyright C 2002 by Wamhoff, Zlotskii, Saprygina. BRIEF ˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝ ˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝ COMMUNICATIONS H. Wamhoff, S. S. Zlotskii, and V. A. Saprygina Kekulé Institut fu 1r Organische Chemie und Biochemie der Universitat 1 Bonn, Bonn, Germany Ufa State of University of Petroleum Engineering, Ufa, Bashkortostan, Russia Reaktiv Research Institute, Ufa, Bashkortostan, Russia Received July 9, 2001 Abstract-4-Arylurazoles are selectively oxidized with Fe (NO ) . 9H O to the corresponding D -1,2,4-tri- 2 3 3 2 azoline-3,5-diones. Recently there has been growing interest inD -1,2,4- HCl was added to pH < 2, and the resulting bright red triazoline-3,5-diones, which are extremely active di- liquid was diluted with an equal volume of ice-cold enophiles and are successfully used in syntheses of water. The precipitate was filtered off, washed with fused and polysubstituted heterocycles [133]. Also, water, and vacuum-dried. Target compounds IIa3IIc these compounds react with olefins to form the cor- were obtained in 65 375% yields; their constants responding secondary amines [4, 5]. The most ver- agreed with published data [9, 10]. satile and widely used route to D -1,2,4-triazoline-3,5- ACKNOWLEDGMENTS diones is oxidation of the corresponding urazoles (1,2,4-triazolidine-3,5-diones). The study was performed within the framework Along with the use of powerful oxidants, such as of the Academic Exchange Program of the German tert-butyl hypochlorite [6], trichloroacetyl isocyanate Academy (DAAD), grant A/99/09 940. [7], or nitrogen dioxide [8], procedures have been developed for oxidation with N-bromosuccinimide REFERENCES [9, 10] and halogens [11]: 1. The Chemistry of Heterocyclic Compounds, Mont- O O i i i i gomery, J.A., Ed., New York: Wiley, 1981, vol. 37. NH 3C N 3C f [O] f g g g c c 2. Adam, W. and Lucchi, O. de, Angew. Chem., 1980, N R N R, g g g g g g vol. 92, no. 10, pp. 815 3 832. h h NH 3C N 3C e e 3. Wagner, Th.J., Synthesis, 1980, no. 7, pp. 165 3214, e e O O 769 3798. Ia3Ic IIa3IIc 4. Adam, W., Pastor, A., and Wirth, T., Org. Lett., 2000, vol. 5, pp. 1295 31297. where R = Ph (a), 4-ClC H (b), 3,4-Cl C H (c). 6 4 2 6 3 5. Vassilikogiannakis, G., Stratakis, V., Orfanopoulus, M., In addition to the known procedures, we found that and Foote, C.S.D., J. Org. Chem., 1999, vol. 64?, 4-arylurazoles Ia3Ic can be oxidized to 4-aryl-D -1,2,4- no. 11, pp. 4130 3 4139. triazoline-3,5-diones IIa3IIc with iron(III) nitrate un- 6. Cookson, R.C., Gupte, S.S., Stevens, J.D.R., and der mild conditions in high yields (65 375%). The re- Watts, C.T., Org. Synth., 1971, vol. 51, pp. 1213127. action occurs in the solid phase, which considerably 7. Moore, J.A., Muth, R., and Sorace, R., J. Org. Chem., simplifies the isolation and purification of the target 1974?, vol. 39, no. 25, pp. 3799 33800. diones IIa3IIc. A similar procedure has been used 8. Stickler, J.C. and Pirkle, W.H., J. Org. Chem., 1966, previously to prepare substituted semicarbazides [12]. vol. 31, no. 10, pp. 3444 33445. 9. Wamhoff, H. and Wald, K., Org. Prep. Proced. Int., EXPERIMENTAL 1975, vol. 7, pp. 2513253. 10. Fieser M. and Fieser, L.F., Reagents of Organic Syn- 4-Aryl- D -1,2,4-triazoline-3,5-diones IIa 3IIc. thesis, New York: Wiley, 1977, vol. 6. A mixture of triazolidinedione Ia3Ic with Fe (NO ) . 11. Wamhoff, H. and Kunz, G., Angew. Chem., 1981, 2 3 3 9H O (molar ratio 1 : 2) was ground in an agate mor- vol. 93, no. 9, pp. 8323833. tar for 53 8 min. The mixture was transferred into dry 12. Wang, C., Wang, J., and Li, J., Synth. Commun., 1999, acetone (15 ml per millimole of Ia3Ic), concentrated vol. 29, no. 15, pp. 2597 32599. 1070-4272/02/7502-0332 $27.00 C 2002 MAIK [Nauka/Interperiodica]

Journal

Russian Journal of Applied ChemistrySpringer Journals

Published: Oct 13, 2004

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