Abstract
The review considers the synthetic potential of 4,4-alkoxybutan-2-ones which are promising synthons available from diacetylene-containing industrial gases. The reactivity of 4,4-dialkoxybutan-2-ones toward mono- and difunctional reagents, as well as in cycloaddition processes, is discussed.
Similar content being viewed by others
REFERENCES
Temkin, O.N., Shestakov, T.K., and Treger, Yu.A., Atsetilen. Khimiya. Mekhanizmy reaktsii. Tekhnologiya (Acetylene: Chemistry, Reaction Mechanisms, and Technology), Moscow: Khimiya, 1991.
Shostakovskii, M.F. and Bogdanova, A.V., Khimiya diatsetilena (Chemistry of Diacetylene), Moscow: Nauka, 1971.
Maretina, I.A., Zh. Prikl. Khim., 1996, vol. 69, p. 353.
Maretina, I.A., Zh. Prikl. Khim., 2000, vol. 73, p. 659.
Maretina, I.A. and Tsil’ko, A.E., Khim. Promst., 2003, vol. 81, p. 19.
Maretina, I.A., Khim. Promst., 2004, vol. 82, p. 3.
Mitrosyan, G.V., Matsoyan, V.A., Asratyan, G.V., and Maretina, I.A., USSR Inventor’s Certificate no. 1 770 318, 1992; Byull. Izobret., 1992, no. 39.
Rittinger, S. and Rieber, N., Ger. Offen. no. 4 308 073, 1994; Chem. Abstr., 1994, vol. 121, no. 255 823.
Rittinger, S. and Rieber, N., Eur. Patent no. 594 100, 1994; Chem. Abstr., 1994, vol. 121, no. 107 973 p.
Rittinger, S. and Rieber, N., Eur. Patent no. 607 811, 1994; Chem. Abstr., 1994, vol. 121, no. 133 533 q.
Rittinger, R. and Rieber, N., Ger. Offen. no. 4 308 080, 1994; Chem. Abstr., 1994, vol. 121, no. 255 250.
Kaestner, R., Rittinger, R., Paessler, P., and Nieber, N., Ger. Offen. no. 4137011, 1993; Chem. Abstr., 1993, vol. 119, no. 28 138 a.
Michel, H.J., Lang, S., Grabarse, M., Lemnitzer, B., and Thieme, H., Ger. Offen. no. 4 237 687, 1994; Chem. Abstr., 1994, vol. 121, no. 83 331.
Maretina, I.A. and Trofimov, B.A., Usp. Khim., 2000, vol. 69, p. 642.
Rybinskaya, M.I., Nesmeyanov, A.N., and Kochetkov, N.K., Usp. Khim., 1969, vol. 38, p. 961.
Franke, W. and Kuther, J., Fette Seifen Anstrichmittel, 1980, vol. 82, p. 82.
Franke, W., Fenkler, R.D., and Kuther, J., Fette Seifen Anstrichmittel, 1980, vol. 82, p. 370.
Takami, M., Ninagava, Y., and Omura, Y., Heterocycles, 1981, vol. 16, p. 146.
Maretina, I.A., Tsil’ko, A.E., and Zaichenko, Yu.A., Usp. Khim., 1981, vol. 50, p. 1249.
Shrot, B., Khim. Geterotsikl. Soedin., 1985, p. 1443.
Maretina, I.A., Usp. Khim., 1991, vol. 60, p. 103.
Maretina, I.A. and Trofimov, B.A., Adv. Heterocycl. Chem., 2002, vol. 82, p. 157.
Catalog Handbook of Fine Chemicals (Aldrich), Milwaukee, WI: Aldrich Chemical Company, 2003–2004.
Nishihira, K., Tanaka, S., and Kodo, M., US Patent no. 5 276 200, 1994; Chem. Abstr., 1994, vol. 120, no. 298 076.
Guidotti, B.R., Herzog, E., Bangerter, F., and Caseri, W., J. Colloid Interface Sci., 1997, vol. 191, p. 209; Chem.Abstr., 1997, vol. 127, no. 225 587.
Tagushi, S., Yoshida, Y., and Nezu, H., Eur. Patent no. 814 130, 1996; Chem. Abstr., 1998, vol. 128, no. 76 680.
Nogami, G., Ykemoto, K., and Aoyama, T., JPN Patent no. 188 361, 2001; Chem. Abstr., 2001, vol. 135, no. 99 838.
Priddy, D.B., US Patent no.5 187 249, 1993; Chem. Abstr., 1993, vol. 118, no. 255 992.
Myamoto, Y. and Minami, M., JPN Patent no. 06-271 531, 1994; Chem. Abstr., 1995, vol. 122, no. 105 524.
Kawai, A., Kawai, M., Murata, Y., and Takada, Y., PCT WO 98-02 430, 1998; Chem. Abstr., 1998, vol. 128, no. 140 613.
Popjak, G., Edmond, J., Anet, F.A.L., and Easton, N.R., J. Am. Chem. Soc., 1977, vol. 99, p. 931.
Danishefsky, S.J., Larson, E., Askin, D., and Kato, N., J. Am. Chem. Soc., 1985, vol. 107, p. 1246.
Danishefsky, S.J., Aldrichim. Acta, 1986, vol. 19, p. 59.
Bednarski, M. and Danishefsky, S.J., J. Am. Chem. Soc., 1986, vol. 108, p. 7060.
Kozmin, S.A., Janey, J.M., and Vires, H., J. Org. Chem., 1999, vol. 64, p. 3039.
Tanaka, K. and Fu, G.C., J. Am. Chem. Soc., 2002, vol. 124, p. 10 296.
Tanaka, K. and Fu, G.C., J. Am. Chem. Soc., 2001, vol. 123, p. 11 492.
Enders, D. and Meyer, O., Justus Liebigs Ann. Chem., 1996, p. 1023.
Paterson, I. and Osborne, S., Tetrahedron Lett., 1990, vol. 31, p. 2213.
Kozmin, S.A., Iwama, T., Huang, J.R., and Virech, H., J. Am. Chem. Soc., 2002, vol. 124, p. 4628.
Kozmin, S.A., Org. Lett., 2001, vol. 3, p. 755.
Kozmin, S.A. and Rawal, V.H., J. Org. Chem., 1997, vol. 62, p. 5252.
Kozmin, S.A. and Rawal, V.H., J. Am. Chem. Soc., 1997, vol. 119, p. 7165.
Berger, D., Wilhelm, P., and Neuenschwander, M., Helv. Chim. Acta, 1999, vol. 82, p. 326.
Petrov, A.A., Maretina, I.A., Tsil’ko, A.E., Ostroumov, I.G., Asratyan, G.V., Morlyan, N.M., and Matevosyan, R.O., Katalog po produktam sinteza na osnove 1,1-dialkoksibutan-3-ona (Synthetic Products from 1,1-Dialkoxybutan-3-ones. Catalog), Erevan: LTI, AF IREA Reakhrom, 1991.
Ham, W.H., Yang, J.G., Lee, M.S., and Song, J.N., Arch. Pharmacol. Res., 1993, vol. 16, p. 257; Chem. Abstr., 1994, vol. 121, no. 56 946.
Kii, S. and Maruoka, K., Tetrahedron Lett., 2001, vol. 42, p. 1935.
Seltser, S., J. Org. Chem., 1995, vol. 60, p. 1189.
Seltser, S., J. Am. Chem. Soc., 1994, vol. 116, p. 9383.
Hecquet, L., Bolte, J., and Demuynck, C., Tetrahedron, 1994, vol. 50, p. 8677.
Wong, C.H., Durrwachter, J.R., and Pederson, R., US Patent no. 5 143 831, 1992; Chem.Abstr., 1993, vol. 118, no. 21 060.
Yamano, Y, Tode, C., and Ito, M., J. Chem Soc., Perkin Trans 1, 1998, p. 2569.
Ono, M., Yoshida, N., and Akita, H., Chem. Pharm. Bull., 1997, vol. 45, p. 1740; Chem. Abstr., 1998, vol. 128, no. 75 213.
Jacobs, H.A.M., Berg, M.H., Brandsma, L., and Arens, J.F., Recl. Trav. Chim. Pays-Bas, 1965, vol. 84, p. 1113.
Valla, A. and Pierre, J.P., PCT WO 02-34 710, 2002; Chem. Abstr., 2002, vol. 136, no. 340 852.
Thuenemann, A.F. and Beyermann, J., Macromolecules, 2000, vol. 33, p. 6878; Chem. Abstr., 2000, vol. 133, no. 252 928.
Paczkowski, R., Maichle-Moessmer, C., and Maier, M.E., Org. Lett., 2000, vol. 2, p. 3967; Chem. Abstr., 2000, vol. 134, no. 86 394.
Cromber, L., Narper, S.H., and Sleep, K.S., J. Chem. Soc., 1957, p. 2743.
Ito, N., Kinoshita, K., and Eto, T., JPN Patent no. 04-41 455, 1992; Chem. Abstr., 1992, vol. 112, no. 48 950.
Schulz, S., Seffensky, M., and Roisin, J., Justus Liebigs Ann. Chem., 1996, p. 941.
Kucherov, V.F., Yanovskaya, L.A., and Kovalev, V.G., Dokl. Akad. NaukSSSR, 1960, vol. 133, p. 370.
Chen, J., Sakamoto, K., Orita, A., and Otera, J., Tetrahedron, 1998, vol. 54, p. 8411.
Zaichenko, Yu.A., Tsil’ko, A.E., and Maretina, I.A., Zh. Org. Khim., 1984, vol. 20, p. 963.
Markova, N.K., Zaichenko, Yu.A., Tsil’ko, A.E., and Maretina, I.A., USSR Inventor’s Certificate no. 1 122 652, 1983; Chem. Abstr., 1985, vol. 102, no. 203 877.
Kukhar’, V.P., Vdovenko, S.I., and Gerus, I.I., Dokl. Akad. Nauk Ukrainy, 1991, p. 129.
Vdovenko, S.I., Gerus, I.I., and Wojcik, D., J. Phys. Org. Chem., 2001, vol. 14, p. 533.
Vdovenko, S.I., Gerus, I.I., and Gorbunova, M.G., J. Fluorine Chem., 1997, vol. 82, p. 167.
Sauer, J.D., Smith, K.R., and Borland, J.E., US Patent no.5 103 053, 1991; Chem.Abstr., 1992, vol. 116, no. 235 068.
Gerus, I.I., Kacharova, L.M., and Vdovenko, S.I., Synthesis, 2001, p. 431.
Campos, P.J., Tan, Ch. Q., and Rodriquez, M.A., Tetrahedron Lett., 1995, vol. 36, p. 5257.
Katritzky, A.R., Blitzke, T., and Li, J., Synth. Commun., 1996, vol. 26, p. 3773.
Tomcufcik, A.S., Meyer, W.D., and Marsico, J.W., Eur. Patent no. 446 604, 1991; Chem. Abstr., 1992, vol. 116, no. 235 068.
McAlonan, H. and Murphy, J.P., J. Chem. Soc., Perkin Trans 1, 1992, p. 69.
Cook, G.R., Beholz, L.G., and Still, J.R., J. Org. Chem., 1994, vol. 59, p. 3575.
Quintanilla-Licca, R. and Teuber, H.J., Arch. Pharm., 1992, vol. 325, p. 557; Chem. Abstr., 1992, vol. 117, no. 251 250.
Teuber, H.J., Angew. Chem., 1965, vol. 77, p. 224.
Laronze, J.Y., Laronze, J., and Wemba-Lenga, F., Heterocycles, 1992, vol. 34, p. 1101.
Teuber, H.J., Glosauer, U., and Hochmuth, O., Chem. Ber., 1964, vol. 97, p. 557.
Rosenmund, P., Hosseini-Merescht, M., and Bub, C., Justus Liebigs Ann. Chem., 1994, p. 151.
Teuber, H.J. and Quintanilla-Licea, R., Chem. Z., 1994, vol. 336, p. 452.
Bajawa, J.S. and Sykes, P.J., J. Chem. Soc., Perkin Trans 1, 1979, p. 3085.
Juh-Wen Ho, J. Chin. Chem. Soc., 1999, vol. 46, p. 955; Chem. Abstr., 2000, vol. 132, no. 194 356.
Bamaung, N.J., Basha, A., Djuric, S.W., Gubbins, F.G., and Luly, Y.R., US Patent no. 44 445, 2001; Chem. Abstr., 2002, vol. 136, no. 5986.
Hogenkamp, D.J., Nguyen, P., and Jang, G., PCT WO 01-72 714, 2001; Chem. Abstr., 2001, vol. 135, no. 272 968.
Hogenkamp, D.J., Nguyen, P., and Shao, B., PCT WO 01-68 612, 2001; Chem. Abstr., 2001, vol. 135, no. 257 270.
Selleri, S., Bruni, F., Costagly, E., Costanzo, A., Guerrini, G., and Ciciani, G., Bioorg. Med. Chem., 2001, vol. 9, p. 2661; Chem. Abstr., 2001, vol. 136, no. 79 252.
Bunnage, M.E., Mathias, J.P., Street, S.D., and Dereck, A., PCT WO 99-54 333, 1998; Chem. Abstr., 1999, vol. 131, no. 310 644.
Kuroki, Y., Takamura, S., Ueno, H., and Nakakoshi, I., JPN Patent no. 06-09 638, 1994; Chem. Abstr., 1994, vol. 121, no. 108 820.
Zvilichovsky, G. and Gurvich, V., J. Chem. Soc., Perkin Trans. 1, 1995, p. 2509.
Guerret, P., Jacquier, R., and Maury, G., Bull. Soc. Chim. Fr., 1972, p. 3503; Chem. Abstr., 1972, vol. 78, p. 4206.
Chambers, M.S., Goodacre, S.C., Hallet, D.I., and Jennings, A.Y., PCT WO 02-74 772, 2002; Chem. Abstr., 2002, vol. 137, no. 263 047.
Chambers, M.S., Goodacre, S.C., Hallet, D.I., and Jennings, A.Y., PCT WO 02-74 773, 2002; Chem. Abstr., 2002, vol. 137, no. 263 948.
Alanin, A., Buettelmann, B., Heitz, N., and Jaeschke, G., PCT WO 02-60 877, 2002; Chem. Abstr., 2002, vol. 137, no. 154 932.
Kleschick, W.A., Gerwick, B., and Clefford, Synth. Chem. Agrochem III, ACS. Symp. Ser. 1992, vol. 504, p. 26; Chem. Abstr., 1993, vol. 118, p. 38 888.
Mori, I., Kimura, Y., Matsunaga, S., and Nakano, T., PCT WO 95-18 818, 1995; Chem. Abstr., 1995, vol. 123, no. 286 292.
Vel’chinskaya, E.V., Kuzmenko, I.I., and Kulik, L.S., Pharm. Chem. J., 1999, vol. 33, p. 155; Chem. Abstr., 2000, vol. 132, no. 13 735.
Pilkington, B.L. and Worthington, P.A., Eur. Patent no. 495 662, 1990; Chem. Abstr., 1992, vol. 116, no. 128 954.
Kasahara, I., Ihama, T., Hashimito, A., and Sano, S., JPN Patent no. 05-213 878, 1993; Chem. Abstr., 1993, vol. 119, no. 264 649.
Nasarina, M., Sharifian, A., and Shafiee, A., J. Heterocycl. Chem., 1995, vol. 32, p. 223.
Bunnage, M.E. and Mathias, J.P., PCT WO 99-54 333, 1998; Chem. Abstr., 1999, vol. 131, no. 3106 44.
Shan, P.W., Cottrell, I.F., and Moloney, M.G., J. Chem. Soc., Perkin Trans. 1, 2001, p. 2297.
Nazarina, M., Sharifian, A., and Shafice, A., J. Heterocycl. Chem., 1995, vol. 32, p. 223.
Baba, M., Ooya, E., Kondo, J., and Navamaki, T., JPN Patent no. 06-25 177, 1994; Chem. Abstr., 1994, vol. 121, no. 83 326.
Takashima, J., Nasuno, I., and Yamamoto, H., PCT WO 96-31 507, 1996; Chem. Abstr., 1997, vol. 126, no. 7984.
Hill, R.L., Rack, M., and Gotz, N., PCT WO 98-29 932, 1998; Chem. Abstr., 1998, vol. 129, no. 95 490.
Manning, D.T, Pilato, M., and Wu, T., PCT WO 98-28 279, 1998; Chem. Abstr., 1998, vol. 129, no. 95 489.
Phillips, J., Pilato, M., and Wu, T., PCT WO 98-28 277, 1998; Chem. Abstr., 1998, vol. 129, 109 087.
Fukami, T., Fukuroda, T., Kanatani, A., and Jhara, M., Ger. Offen. no. 19 653 586, 1998; Chem. Abstr., 1998, vol. 129, no. 81 725.
Ooe, T., Sueoka, H., Kobayashi, H., and Kudome, M., JPN Patent no. 07-02 786, 1995; Chem. Abstr., 1995, vol. 122, no. 239 697.
Moeller, H. and Hoeffkes, H., Ger. Offen. no. 4 314 317, 1995; Chem. Abstr., 1995, vol. 122, no. 38 518.
Pronin, V.A., Usol’tseva, M.V., Shastina, Z.N., Volkov, A.N., and Seraya, V.N., Zh. Neorg. Khim., 1976, vol. 19, p. 800.
Pronin, V.A., Usol’tseva, M.V., Shastina, Z.N., Volkov, A.N., and Sokolyanskaya, L.V., Zh. Anal. Khim., 1976, vol. 31, p. 1767.
Sigridur, S. and Thompson, J.S., PCT WO 95-11 319, 1994; Chem. Abstr., 1995, vol. 123, no. 14 301.
Shcherbinina, N.I., Myasoedova, G.V., Kolobov, S.S., and Druzhinina, T.V., Zh. Anal. Khim., 1995, vol. 50, p. 795.
Sun, Z. and An, J., Gangtie, 1994, vol. 29, p. 57; Chem. Abstr., 1994, vol. 121, no. 184 346.
Brender, E. and Roewer, G., Eur. Patent no. 610 809,1994; Chem. Abstr., 1994, vol. 121, no. 256 035.
Pogorzhel’skaya, N.A., Maretina, I.A., and Petrov, A.A., Zh. Org. Khim., 1969, vol. 5, p. 223.
Chrimishi, S. and Cosimellii, B., Synth. Commun., 1992, vol. 22, p. 2902.
Ohkawa, S., Naruo, K., Mivwatashi, S., and Kimura, H., PCT WO 02-62 792, 2002; Chem. Abstr., 2002, vol. 137, no. 169 523.
Gonzalez, B., Gonzalez, A., and Pulido, F., Synth. Commun., 1995, vol. 25, p. 1005.
Vicentini, C.B., Veronese, A., and Guarneri, M., Eur. Patent no. 190 457, 1986; Chem. Abstr., 1986, vol. 105, no. 226 578.
Diadone, G., Bajarch, M., and Rafa, D., Synth. Commun., 1995, vol. 25, p. 1441.
Kaiser, A. and Stingelin, W., Eur.Patent no. 591 103, 1994; Chem. Abstr., 1994, vol. 121, no. 233 064.
Guethner, T. and Graml, B., Ger. Offen. no. 10 002 832, 2001; Chem. Abstr., 2001, vol. 136, no. 20 085.
Murugan, R., Schriven, F.V., Hillstrom, G.F., and Ghoshal, P.K., PCT WO 02-90 328, 2002; Chem. Abstr., 2002, vol. 137, no. 352 895.
Alberti, M.J., Chamberlain, S.D., and Chueng, M., PCT WO, 02-78 700, 2002; Chem. Abstr., 2002, vol. 137, no. 294 963.
Boyd, F.L. and Goodmundsson, K.J., PCT WO 02-78 701, 2002; Chem. Abstr., 2002, vol. 137, no. 288 973.
Chen, G., Adams, J., Bemis, J., and Booker, S., PCT WO 02-66 470, 2002; Chem. Abstr., 2002, vol. 137, no. 201 332.
Maretina, I.A. and Ostroumov, I.G., Khim. Geterotsikl. Soedin., 1992, p. 867.
Klimko, V.T., Mikhalev, V.A., and Skoldinov, A.P., Zh. Obshch. Khim., 1960, vol. 30, p. 1258.
Bredereck, H., Effenberger, F., and Botsch, R., Chem. Ber., 1965, vol. 98, p. 1081.
Sokolyanskaya, L.V., Volkov, A.N., and Tsetlina, E.O., Zh. Org. Khim., 1976, vol. 12, p. 2063.
Chen, L., Mao, S., and Simon, J., J. Biol. Chem., 1992, vol. 267, p. 12380; Chem. Abstr., 1993, vol. 119, no. 45 457.
Ohkanda, J., Tokumitsu, T., and Katoch, A., Bull. Chem. Soc. Jpn., 1993, vol. 66, p. 841; Chem. Abstr., 1993, vol. 119, no. 139 187.
Kanoch, A., Inokawa, M., and Ohkanda, J., Chem. Pharm. Bull., 1994, vol. 42, p. 1514; Chem. Abstr., 1995, vol. 122, no. 161 267.
Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Khar’kov: Torsing, 1991.
Hodge, C.N., Aldrich, L.E., and Wasserman, Z.R., J. Med. Chem., 1999, vol. 42, p. 819: Chem. Abstr., 1999, vol. 130, no. 320 358.
South, M.S., Parlow, J.J., Jones, D.E., and Case, B., PCT WO 01-87 854, 2001; Chem. Abstr., 2002, vol. 136, no. 6006.
Hucke, A., Michel, H.J., Niclas, H.J., and Kristof, H.A., Ger. Offen. no. 10 024 622, 2001; Chem. Abstr., 2001, vol. 135, no. 371 864.
Sato, M., Parlow, J.J., Jones, D.E., Case, B., and Ischii, T., Patent no. 354 656, 2001; Chem. Abstr., 2002, vol. 136, no. 48 447.
Gericke, R., Beier, N., and Wilm, C., PCT WO 01-79 186, 2001; Chem. Abstr., 2001, vol. 135, no. 318 514.
Amemiya, Y., Wakabayashi, K., Takaishi, S., and Fucuda, C., PCT WO 01-83 427, 2001; Chem. Abstr., 2001, vol. 135, no. 357 944.
Araldi, G.L.and Semple, J.E., PCT WO 01-79 193, 2001; Chem. Abstr., 2001, vol. 135, no. 331 443.
Semple, J.E., Cui, J.J., and Ho, J.Z., PCT WO 01-79 195, 2001; Chem. Abstr., 2001, vol. 135, no. 331 444.
Semple, J.E. and Araldi, G.L., PCT WO 01-79 262, 2001; Chem. Abstr., 2001, vol. 135, no. 331 445.
Kazimierczuk, Z., Lasek, W., and Sickorska, A., PCT WO 01-74 789, 2001; Chem. Abstr., 2001, vol. 135, no. 284 737.
Jinobo, Y. and Miyasako, T., JPN Patent no. 11-292 854, 1998; Chem. Abstr., 1999, vol. 131, no. 310 643.
Davis, J.M., Davis, P.D., Moffat, F.C., and Batchelor, M.J., PCT WO 98-28 281, 1998; Chem. Abstr., 1998, vol. 129, no. 95 505.
Peyman, A., Knolle, J., Weihner, V., and Breipohl, G., BRD Patent no. 19 653 646, 1998; Chem. Abstr., 1998, vol. 129, no. 95 606.
Igarashi, J-E., Nishimura, T, and Sunagawa, M., PCT WO 96-31 488, 1997; Chem. Abstr., 1997, vol. 126, no. 8135.
Crowley, P.J., Whittingham, W.E., and Eshelby, J.J., PCT WO 97-49 696, 1997; Chem. Abstr., 1998, vol. 128, no. 102 097.
Lorenz, H., Tennigkeit, J., and Kufner, F., Eur. Patent no. 663 204, 1995; Chem. Abstr., 1995, vol. 123, no. 179 083.
Lorenz, H., Tennigkeit, J., and Kufner, F., BRD Patent no. 4 400 757, 1995; Chem. Abstr., 1995, vol. 123, no. 179 084.
Henkel, K.G., Ger. Patent no.20 117 916, 2002; Chem. Abstr., 2002, vol. 136, no. 172 477.
Ulrich, P., Fang, S.D., and Brines, M., PCT WO 02-62 301, 2002; Chem. Abstr., 2002, vol. 137, no. 169 535.
Olima, I. and Kumagi, M., Chem. Lett. 1978, p. 575; Chem. Abstr., 1978, vol. 89, no. 129 021.
Overman, L.E. and Wolfe, J.P., J. Org. Chem., 2001, vol. 66, p. 3167; Chem. Abstr., 2001, vol. 135, no. 61 294.
McKenna, J.M., Halley, F., and Sounes, J., J. Med. Chem., 2002, vol. 45, p. 2173; Chem. Abstr., 2002, vol. 137, no. 242 104.
Joseph-McCarthy, D., Tsang, S.K., and Filman, D.Y., J. Am. Chem. Soc., 2001, vol. 123, p. 12 758; Chem. Abstr., 2002, vol. 136, no. 128 664.
Dodd, J.H., Henry, J.R., and Rupert, R.C., PCT WO 01-34 605, 2001; Chem. Abstr., 2001, vol. 134, no. 366 888.
Claiborn, C.F., Claremon, D.A., and Liverton, N.J., PCT WO 01-22 965, 2001; Chem. Abstr., 2001, vol. 134, no. 280 841.
Liverton, N.Y., Claremone, D.A., and Butcher, J.W., PCT WO 01-00 208, 2001; Chem. Abstr., 2001, vol. 134, no. 81 270.
Lukovits, L., Kalman, E., and Zucchi, F., Corrosion, 2001, vol. 57, p. 3; Chem. Abstr., 2001, vol. 134, no. 214 097.
Cho, S., Gong, L., and Muchowsky, J., J. Org. Chem., 1991, vol. 56, p. 7288.
Misak, M., Takada, S., Ychirashi, M., and Fukumoto, S., PCT WO 00-75 515, 2000; Chem. Abstr., 2001, vol. 134, no. 29 326.
Mlakar, B., Stefane, B., Kocevar, M., and Polanc, S., Tetrahedron, 1998, vol. 54, p. 4387.
Mlakar, B., Stefane, B., and Kocevar, M., Heterocycles, 1998, vol. 48, p. 961.
Gupton, B.F., PCT WO 02-30 901,2002; Chem. Abstr., 2002, vol. 136, no. 309 855.
Gorbunova, M.G., Gerus, J.J., and Kukhar’, V.P., J. Fluorine Chem., 1994, vol. 65, p. 25; Chem. Abstr., 1994, vol. 120, no. 191 472.
Fayet, C. and Gelas, J., Carbohydr. Res., 1993, vol. 239, p. 177; Chem. Abstr., 1993, vol. 119, no. 203 681.
Ishimaru, K., JPN Patent no. 04-211 389, 1992; Chem. Abstr., 1993, vol. 118, no. 79 477.
Hanayama, N., Ishimaru, K., and Kamezono, J., JPN Patent no. 05-17 492, 1993; Chem. Abstr., 1993, vol. 119, no. 28 536.
Ishimaru, K. and Kamezono, J., JPN Patent no.05-161 498, 1993; Chem. Abstr., 1993, vol. 119, no. 158 397.
Hanayama, N., Ishimaru, K., and Kamezono, J., Biotechnol. Appl. Biochem., 1992, vol. 56, p. 1136; Chem. Abstr., 1992, vol. 117, no. 192 193.
Donnelly, D., Finet, J.P., and Guiry, P.J., J. Chem. Soc., Perkin Trans. 1, 1992, p. 1365.
Jnaneshwara, G.K., Barhate, N.B., Suctalai, A., and Deshande, V.N., J. Chem Soc., Perkin Trans. 1, 1998, p. 965.
Gajare, A.S., Shingare, M.S., and Bandgar, B.P, J. Chem. Res., Synop., 1999, p. 172.
Berkaoui, M., Outurquin, F., and Paulmier, C., Tetrahedron, 1998, vol. 54, p. 9055.
JPN Patent no. 173 483, 2002; Chem. Abstr., 2002, vol. 137, no. 33 224.
JPN Patent no. 173 482, 2002; Chem. Abstr., 2002, vol. 137, no. 33 223.
Tyvorskii, V.I., Bobrov, D.N., Kulinkovich, O.G., Kimpe, N.D., and Tehrani, K.A., Tetrahedron, 1998, vol. 54, p. 2819.
Tyvorskii, V.I. and Bobrov, D.N., Chem. Heterocycl. Compd., 1998, vol. 33, p. 995.
Ciufolini, M.A. and Xi, N., Chem. Commun., 1994, p. 1867.
Schaper, W., Synthesis, 1985, p. 861.
Mikis, S., Fukuoka, K., Akita, M., Kawakami, J., and Furuya, S., PCT WO 99-09 033, 1999; Chem. Abstr., 1999, vol. 130, no. 196 644.
Markova, N.K., Tsil’ko, A.E., Galisbev, V.A., Maretina, I.A., and Petrov, A.A., Zh. Org. Khim., 1983, vol. 19, p. 2281.
Markova, N.K., Tsil’ko, A.E., Galishev, V.A., and Maretina, I.A., Zh. Org. Khim., 1984, vol. 20, p. 449.
Markova, N.K., Tsil’ko, A.E., Galisbev, V.A., and Maretina, I.A., Zh. Org. Khim., 1984, vol. 20, p. 1589.
Galishev, V.A., Chistokletov, V.N., and Petrov, A.A., Usp. Khim., 1980, vol. 49, p. 1801.
Kozmin, S.A. and Rawal, V.H., J. Am. Chem. Soc., 1998, vol. 120, p. 13523.
Saito, S., Shimada, I., Takamori, Y., and Tanaka, M., Bull. Chem. Soc. Jpn., 1997, vol. 70, p. 1671; Chem. Abstr., 1997, vol. 127, no. 190 478.
Butz, T. and Sauer, J., Tetrahedron: Asymmetry, 1997, vol. 8, p. 703; Chem. Abstr., 1997, vol. 126, no. 305 545.
Van Broek, P.I., Van Doren, P.E., Toppet, S.M., and Hoornaert, G.J., J. Chem. Soc., Perkin Trans. 1, 1992, p. 415.
Ansorge, A., Brauer, D.J., Burger, H., Dorrenbach, H., Hagen, T., Pawelke, G., and Weuter, W., J. Organomet. Chem., 1990, vol. 396, p. 253.
Tominaga, Y., Ichihara, Y., Mori, T., Kamio, C., and Hosomi, A., J. Heterocycl. Chem., 1990, vol. 27, p. 263.
Voronkov, M.G., Trofimov, B.A., Kryuchkov, V.V., Skvortsov, Yu.M., Amosova, S.V., Volkov, A.N., and Mal’kina, A.G., Ger. Offen no. 2 818 580, 1978; Chem. Abstr., 1980, vol. 92, no. 94 228.
Petrov, A.A., Maretina, I.A., Tsil’ko, A.E., Asratyan, G.V., and Matevosyan, R.O., Abstracts of Papers, Vsesoyuznoe soveshchanie po perspektivam rasshireniya assortimenta reaktivov dlya obespecheniya vedushchikh otraslei narodnogo khozyaistva i nauchnykh issledovanii (All-Union Meeting on Prospects in the Extension of Assortment of Chemicals for Leading Branches of Industry and Agriculture and Scientific Research), Yaroslavl’, 1987, p. 26.
Maretina, I.A., Ostroumov, I.G., and Sukhova, L.N., Abstracts of Papers, X Vserossiiskaya konferentsiya “Reaktiv 97. Khimicheskie reaktivy, reagenty, protsessy malotonnazhnoi khimii” (Xth All-Russia Conf. “Chemicals 97. Chemical Reagents and Processes of Small-Scale Chemistry”), Moscow-Ufa, 1997, p. 173.
Author information
Authors and Affiliations
Additional information
__________
Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 1, 2005, pp. 9–32.
Original Russian Text Copyright © 2005 by Maretina.
Rights and permissions
About this article
Cite this article
Maretina, I.A. 4,4-Dialkoxybutan-2-ones as Synthons. Russ J Org Chem 41, 1–27 (2005). https://doi.org/10.1007/s11178-005-0114-1
Received:
Issue Date:
DOI: https://doi.org/10.1007/s11178-005-0114-1