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Unexpected transformations of 1-aza-1,3,4-trienes in alcoholic potassium hydroxide. New classes of aza dienes

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References

  1. Barluenga, J. and Tomas, M., Adv. Heterocycl. Chem., 1993, vol. 57, p. 1; Behforouz, M. and Ahmadian, M., Tetrahedron, 2000, vol. 56, p. 5259; Al-Azmi, A., Elassar, A.-Z.A., and Booth, B.L., Tetrahedron, 2003, vol. 59, p. 2749; Barluenga, J. and Martínez, S., Arkivoc, 2006, part (vii), p. 129; Pinho e Melo, T.M.V.D., Eur. J. Org. Chem., 2006, p. 2873.

    Article  CAS  Google Scholar 

  2. Palacios, F., Gil, M.J., de Marigorta, E.M., and Rodríguez, M., Tetrahedron Lett., 1999, vol. 40, p. 2411; Palacios, F., Gil, M.J., de Marigorta, E.M., and Rodríguez, M., Tetrahedron, 2000, vol. 56, p. 6319; Orlewska, C., Shaker, R.M., Dees, M., and Otto, H.-H., Monatsh. Chem., 2000, vol. 131, p. 889; Martnez, R., Zapata, F., Caballero, A., Espinosa, A., Tárraga, A., and Molina, P., Org. Lett., 2006, vol. 8, p. 3235.

    Article  CAS  Google Scholar 

  3. Klötgen, S. and Würthwein, E.-U., Tetrahedron Lett., 1995, vol. 36, p. 7065; Campos, P.J., Caro, M., and Rodríguez, M.A., Tetrahedron Lett., 2001, vol. 42, p. 3575; Tanaka, K., Kamatani, M., Mori, H., Fujii, S., Ikeda, K., Hisada, M., Itagaki, Y., and Katsumura, S., Tetrahedron Lett., 1998, vol. 39, p. 1185; Kitamura, M., Kudo, D., and Narasaka, K., Arkivoc, 2006, part (iii), p. 148; Vincze, Z., Mucsi, Z., Scheiber, P., and Nemes, P., Eur. J. Org. Chem., 2008, p. 1092; Brandsma, L., Nedolya, N.A., and Trofimov, B.A., Eur. J. Org. Chem., 1999, p. 2663; Maynard, D.F. and Okamura, W.H., J. Org. Chem., 1995, vol. 60, p. 1763; Wang, C., Wang, Z., Liu, L., Wang, C., Liu, G., and Xi, Z., J. Org. Chem., 2006, vol. 71, p. 8565; Meketa, M.L. and Weinreb, S.M., Org. Lett., 2007, vol. 9, p. 853.

    Article  Google Scholar 

  4. Nedolya, N.A., Shlyakhtina, N.I., Sarapulova, G.I., and Brandsma, L., Russ. J. Org. Chem., 2004, vol. 40, p. 35; Nedolya, N.A. and Shlyakhtina, N.I., Russ. J. Org. Chem., 2007, vol. 43, p. 1124.

    Article  CAS  Google Scholar 

  5. Brandsma, L., Nedolya, N.A., Verkruijsse, H.D., Owen, N.L., Li Du, and Trofimov, B.A., Tetrahedron Lett., 1997, vol. 38, p. 6905; Nedolya, N.A., Brandsma, L., Tarasova, O.A., Verkruijsse, H.D., and Trofimov, B.A., Tetrahedron Lett., 1998, vol. 39, p. 2409; Nedolya, N.A., Schlyakhtina, N.I., Klyba, L.V., Ushakov, I.A., Fedorov, S.V., and Brandsma, L., Tetrahedron Lett., 2002, vol. 43, p. 9679; Nedolya, N.A. and Brandsma, L., Russ. J. Org. Chem., 2003, vol. 39, p. 609; Krivdin, L.B. and Nedolya, N.A., Tetrahedron Lett., 2005, vol. 46, p. 7367; Nedolya, N.A., Dmitrieva, L.L., Albanov, A.I., Klyba, L.V., Tarasova, O.A., and Ushakov, I.A., Russ. J. Org. Chem., 2006, vol. 42, p. 465; Nedolya, N.A. and Brandsma, L., Russ. J. Org. Chem., 2006, vol. 42, p. 607; Nedolya, N.A., Tarasova, O.A., Albanov, A.I., Ushakov, I.A., and Brandsma, L., Russ. J. Org. Chem., 2007, vol. 43, p. 463; Nedolya, N.A., Tarasova, O.A., Albanov, A.I., Volostnykh, O.G., Brandsma, L., and Trofimov, B.A., Mendeleev Commun., 2008, vol. 18, p. 164.

    Article  CAS  Google Scholar 

  6. Tarasova, O.A., Nedolya, N.A., Brandsma, L., and Albanov, A.I., Tetrahedron Lett., 2004, vol. 45, p. 5881; Nedolya, N.A., Tarasova, O.A., Volostnykh, O.G., and Albanov, A.I., Khim. Geterotsikl. Soedin., 2008, p. 1380; Nedolya, N.A., Tarasova, O.A., Albanov, A.I., Klyba, L.V., and Trofimov, B.A., Russ. J. Gen. Chem., 2009, vol. 79, p. 1041.

    Article  CAS  Google Scholar 

  7. Nedolya, N.A., Brandsma, L., van der Kerk, A.H.T.M., Vvedensky, V.Yu., and Trofimov, B.A., Tetrahedron Lett., 1998, vol. 39, p. 1995; Nedolya, N.A., Brandsma, L., Verkruijsse, H.D., van der Kerk, A.H.T.M., and Trofimov, B.A., Tetrahedron Lett., 1998, vol. 39, p. 2631.

    Article  CAS  Google Scholar 

  8. Nedolya, N.A., Novel Chemistry Based on Isothiocyanates and Polar Organometallics, Thesis Utrecht University, Utrecht, The Netherlands, 1999.

  9. Brandsma, L. and Nedolya, N.A., Synthesis, 2004, p. 735; Nedolya, N.A., Khim. Geterotsikl. Soedin., 2008, p. 1443; Trofimov, B.A. and Nedolya, N.A., Comprehensive Heterocyclic Chemistry III, Katritzky, A.R., Ramsden, C.A., Scriven, E.F.V., and Taylor, R.J.K., Eds., Amsterdam: Elsevier, 2008, vol. 3, p. 45.

  10. Nedolya, N.A., Tarasova, O.A., Albanov, A.I., and Klyba, L.V., Materialy mezhdunarodnoi konferentsii po organicheskoi khimii “Organicheskaya khimiya ot Butlerova i Beil’shteina do sovremennosti” (Proc. Int. Conf. on Organic Chemistry “Organic Chemistry from Butlerov and Beilstein to Present”), St. Petersburg, June 26–29, 2006, p. 316.

  11. Tennant, J., Comprehensive Organic Chemistry, Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon, 1979, vol. 2. Translated under the title Obshchaya organicheskaya khimiya, Moscow: Khimiya, 1982, vol. 3, p. 476.

    Google Scholar 

  12. Baldwin, J.E., Urban, F.J., Cooper, R.D.G., and Jose, F.L., J. Am. Chem. Soc., 1973, vol. 95, p. 2401; Koppel, G.A. and Koehler, R.E., J. Am. Chem. Soc., 1973, vol. 95, p. 2403.

    Article  CAS  Google Scholar 

  13. Li, G., Fronczek, F.G., and Antilla, J.C., J. Am. Chem. Soc., 2008, vol. 130, p. 12 216.

    CAS  Google Scholar 

  14. Kokotos, C.G. and Aggarwal, V.K., Org. Lett., 2007, vol. 9, p. 2099; Conejo-García, A., Núñez, M.C., Marchal, J.A., Rodríguez-Serrano, F., Aránega, A., Gallo, M.A., Espinosa, A., and Campos, J.M., Eur. J. Med. Chem., 2008, vol. 43, p. 1742; Adam, M.S.S., Kühl, O., Kindermann, M.K., Heinicke, J.W., and Jones, P.G., Tetrahedron, 2008, vol. 64, p. 7960; Sizun, G., Dukhan, D., Griffon, J.-F., Griffe, L., Meillon, J.-C., Leroy, F., Storer, R., Sommadossi, J.-P., and Gosselin, G., Carbohydr. Res., 2009, vol. 344, p. 448.

    Article  CAS  Google Scholar 

  15. Hoff, S., Brandsma, L., and Arens, J.F., Recl. Trav. Chim. Pays-Bas, 1968, vol. 87, p. 916.

    Article  CAS  Google Scholar 

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Correspondence to N. A. Nedolya.

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Original Russian Text © N.A. Nedolya, O.A. Tarasova, O.G. Volostnykh, A.I. Albanov, B.A. Trofimov, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 1, pp. 146–149.

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Nedolya, N.A., Tarasova, O.A., Volostnykh, O.G. et al. Unexpected transformations of 1-aza-1,3,4-trienes in alcoholic potassium hydroxide. New classes of aza dienes. Russ J Org Chem 47, 146–149 (2011). https://doi.org/10.1134/S1070428011010209

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  • DOI: https://doi.org/10.1134/S1070428011010209

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