Abstract
A new procedure was developed for the synthesis of 8-alkoxycarbonylangelicins by base-catalyzed cyclization of ortho-acyl(hydroxy)coumarins with haloacetic acid esters. The procedure was successfully applied to prepare a series of new 8-alkoxycarbonyl- and 8-acylangelicins.
Similar content being viewed by others
REFERENCES
Murray, R.D.H., The Natural Coumarins: Occurrence, Chemistry, and Biochemistry, New York: Wiley, 1982, pp. 290-311.
Edelson, R.L., J. Photochem. Photobiol., B: Biology, 1991, vol. 10, no. 1, pp. 165-174.
Van Iperen, H.P. and Van Henegouwen, G.M.J.B., J. Photochem. Photobiol., B: Biology, 1997, vol. 39, no. 2, pp. 99-109.
Dall'Acqua, F. and Caffieri, S., Photomed. Photobiol., 1988, vol. 10, no. 1, pp. 1-46.
Averbeck, D., Photochem. Photobiol., 1989, vol. 50, no. 5, pp. 859-882.
Averbeck, D. and Moustacchi, E., Photochem. Photobiol., 1980, vol. 31, no. 5, pp. 475-478.
Rodighiero, G., Dall'Acqua, F., and Pathak, M.A., Topics in Photomedicine, New York: Plenum, 1984, pp. 319-398.
Bordin, F., Carlassare, F., Baccichetti, F., Guiotto, A., Rodighiero, P., Vedaldi, D., and Dall'-Acqua, F., Photochem. Photobiol., 1979, vol. 29, no. 6, pp. 1063-1070.
Dall'Aqua, F., Vedaldi, D., Bordin, F., Carlassare, F., Baccichetti, F., Tamaro, M., Rodighiero, P., Pastorini, G., Guiotto, A., Recchia, G., and Cristofolini, M., J. Med. Chem., 1983, vol. 26, no. 6, pp. 870-876.
Guiotto, A., Rodighiero, P., Manzini, P., Pastorini, G., Bordin, F., Baccichetti, F., Carlassare, F., Vedaldi, D., Dall'Acqua, F., Tamaro, M., Recchia, G., and Cristofolini, M., J. Med. Chem., 1984, vol. 27, no. 8, pp. 959-967.
Knox, C.N., Land, E.J., and Truscott, T.G., J. Photochem. Photobiol., B: Biology, 1988, vol. 1, no. 3, pp. 315-321; Carlossare, F., Baccichetti, F., Guiotto, A., Rodighiero, P., Gia, O., Cappozzi, A., Pastorini, G., and Bordin, F., J. Photochem. Photobiol., B: Biology, 1990, vol. 5, no. 1, pp. 25–39; Magnos, S.M., Rodighiero, P., Gia, O., Bordin, F., Baccichetti, F., and Guiotto, A., Farmaco, Ed. Sci., 1981, vol. 36, no. 7, pp. 629–647; Iester, M., Fossa, P., Menozzi, G., Mosti, L., Baccichetti, F., Marzano, C., and Simonato, M., Farmaco, 1995, vol. 50, no. 10, pp. 669–687; Jones, S.G., Young, A.R., and Truscott, T.G., J. Photochem. Photobiol., B: Biology, 1993, vol. 21, nos. 2–3, pp. 223–227; Marciani, S., Guiotto, A., Rodighiero, P., Gia, O., Rodighiero, G., and Pathak, M.A., Farmaco, Ed. Sci., 1979, vol. 34, no. 3, pp. 234–244; Marzano, C., Caffieri, S., Iester, M., Bordin, F., and Averbeck, D., Med., Biol., Environ., 1994, vol. 22, no. 1, pp. 15–19; Mosti, L., Iester, M., Carlassare, F., Bordin, F., Simonato, M., and Baccichetti, F., Med., Biol., Environ., 1993, vol. 21, no. 2, pp. 595–598; Marzano, C., Caffieri, S., Fossa, P., and Bordin, F., J. Photochem. Photobiol., B: Biology, 1997, vol. 38, nos. 2–3, pp. 189–195.
Zawadowski, T. and Checinski, M., Roczn. Chem., 1977, vol. 51, nos. 7-8, pp. 1511-1514; Kawase, Y., Nakayama, M. and Tamatsukuri, H., Bull. Chem. Soc. Jpn., 1962, vol. 35, nos. 1–2, pp. 149–151; Salvi, V.S. and Sethna, S., J. Indian Chem. Soc., 1968, vol. 45, no. 5, pp. 439–445.
Traven, V.F., Kravtchenko, D.V., and Chibisova, T.A., Mendeleev Commun., 1995, no. 1, pp. 21-22; Traven, V.F., Kravtchenko, D.V., and Chibisova, T.A., Mendeleev Commun., 1997, no. 6, pp. 249–250; Traven, V.F., Kravtchenko, D.V., Chibisova, T.A., Shorshnev, S.V., Eliason, R., and Wakefield, D.H., Heterocycl. Commun., 1996, vol. 2, no. 4, pp. 345–354; Kravtchenko, D.V., Chibisova, T.A., and Traven, V.F., Heterocycl. Commun., 1997, vol. 3, no. 4, pp. 331–338; Traven, V.F., Rozhkov, R.V., Tolmachev, A.Yu., Kuznezova, N.A., Podhaluzina, N.Ya., and Carberry, E.A., Heterocycl. Commun., 1997, vol. 3, no. 4, pp. 339–344.
Thaker, N.N. and Trivedi, K.N., Indian J. Chem., Ser. A., 1981, vol. 20, no. 6, pp. 560-563.
Malhotra, U. and Joshi, S.S., J. Indian Chem. Soc., 1967, vol. 44, no. 1, pp. 80-81; Geetanjali, Y., Rajitha, B., and Kanakalingeswara, R., Indian J. Chem., Ser. B, 1983, vol. 22, no. 2, pp. 164–165; Geetanjali, Y., Rajitha, B., and Kanakalingeswara, R., Bull. Chem. Soc. Jpn., 1986, vol. 59, no. 4, pp. 1299–1301; Masur, J., Grabowska, M., Zawadowski, T., and Balicka, E., Acta Pol. Pharm., 1989, vol. 46, no. 1, pp. 1–4.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Tolmachev, A.Y., Podkhalyuzina, N.Y., Kuznetsova, N.A. et al. New Synthesis of 8-Alkoxycarbonylangelicins. Russian Journal of Organic Chemistry 37, 1008–1012 (2001). https://doi.org/10.1023/A:1012434702051
Issue Date:
DOI: https://doi.org/10.1023/A:1012434702051