Abstract
Data on methods of transforming furans into heterocycles containing oxygen, nitrogen, sulfur, and selenium are discussed and summarized.
Similar content being viewed by others
References
A. P. Dunlop and F. N. Peters, The Furans, Reinhold, New York (1953).
A. A. Ponomarev, Syntheses and Reactions of Furan Substances [in Russian], Izd. SGU, Saratov (1960).
É. Ya. Lukevits (ed.), Advances in the Chemistry of Furans [in Russian], Zinatne, Riga (1978).
F. M. Dean, Adv. Heterocycl. Chem.,30, 167 (1982).
F. M. Dean, Adv. Heterocycl. Chem.,31, 237 (1982).
I. F. Bel'skii and V. M. Shostakovskii, Catalysis in the Chemistry of Furan [in Russian], Nauka, Moscow (1972).
M. B. Shimanskaya (ed.), Catalytic Reactions of Furan Compounds [in Russian], Zinatne, Riga (1985).
B. Bossard and C. H. Eugster, Adv. Heterocycl. Chem.,7, 377 (1966).
H. C. Van der Plas, Ring Transformation of Heterocycles, Academic Press, London-New York (1973).
Yu. K. Yur'ev, Uch. Zap. MGU,79, 7 (1945).
Yu. K. Yur'ev, Uch. Zap. MGU,175, 159 (1956).
R. B. Bishop and W. J. Denton, U. S. Patent No. 2,478,452; Chem. Abs.,44, 665 (1969).
T. Kawagushi, T. Kita, and H. Naito, Japanese Patent No. 6,819,940; Chem. Abs.,70, 68133 (1969).
M. Nomura, T. Tomogane, and S. Kikkawa, Sekiyu Gakkai Shi,20, 419 (1977).
A. A. Avots, A. Aizbalts, and I. Ya. Lazdyn'sh, Inventor's Certificate No. 467,069; Byul. Izobr., No. 14, 43 (1975).
A. A. Avots, I. Ya. Lazdyn'sh, M. K. Sile, and V. S. Aizbalts, Izv. Akad. Nauk LatvSSR. Ser. Khim., No. 3, 333 (1978).
A. Baranski and G. Hejnar, Przem. Chem.,72, 270 (1993).
B. Buchholz, T. E. Deger, and R. H. Goshorn, German Patent No. 1,228,273; Chem. Abs.,66, 18665 (1967).
E. Worbs, H. Magerlein, and G. Meyer, German Patent No. 1,936,565, Ref. Zh. Khim.,15H, 189 (1978).
A. V. Mashkina and A. Kh. Sharipov, Inventor's Certificate No. 1,498,768, Ref. Zh. Khim.,2H, 97 (1990).
Yu. K. Yur'ev and I. S. Levi, Vestnik MGU, Khimiya, No. 2, 153 (1956).
T. Javamoto and M. Jwasaki, Japanese Patent No. 01,301,658; Chem. Abs.,112, 191731 (1990).
M. Jwasaki and T. Javamoto, Japanese Patent No. 01,268,681; Chem. Abs.,112, 158049 (1990).
H. Sugiyama, T. Mori, N. Shimada, F. Morita, and K. Miyaji, Japanese Patent No. 04,342,578, Chem. Abs.,118, 212869 (1993).
K. V. Topchieva, A. A. Kubasov, Van Dao Tyong, and N. N. Kogai, Modern Problems of Physical Chemistry [in Russian], Vol. 8, MGU, Moscow (1975), Vol. 8, p. 326.
K. Hatada, M. Shimada, K. Fujita, Y. Ono, and T. Keii, Chem. Lett.,5, 439 (1974).
K. Fujita, K. Hatada, Y. Ono, and T. Keii, J. Catalysis,35, 325 (1974).
M. Kubo and K. Yasuda, Japanese Patent No. 75,112,361; Chem. Abs., 59181 (1984).
Daicel Chem. Industries, Japanese Patent No. 5,890,548; Chem. Abs., 99, 105121 (1983).
M. Kubo and K. Yasuda, Japanese Patent No. 75,112,362, Chem. Abs.,84, 59180 (1976).
J. Ono, K. Hatada, and K. Fujita, J. Catalysis,41, 322 (1976).
Van Dao Tyong, A. A. Kubasov, and K. B. Topchieva, Vestnik MGU Khimiya,14, 146 (1973).
F. Sorm and Z. Arnold, Coll. Czech. Chem. Commun.,12, 467 (1947).
A. A. Ponomarev, N. P. Maslennikova, N. V. Alakina, and A. P. Kriven'ko, Dokl. Akad. Nauk,131, 1355 (1960).
A. A. Ponomarev and I. M. Skvortsov, Zh. Obshch. Khim.,32, 97 (1962).
A. A. Ponomarev, V. N. Dyukareva, and I. M. Skvortsov, Dokl. Akad. Nauk,178, 893 (1968).
A. A. Ponomarev and V. M. Levin, Khim. Geterotsikl. Soedin., No. 5, 939 (1969).
A. A. Ponomarev, I. M. Skvortsov, and A. A. Khorkin, Zh. Obshch. Khim.,33, 2687 (1963).
A. A. Ponomarev, I. M. Skvortsov, and L. N. Astakhova, Dokl. Akad. Nauk,155, 861 (1964).
L. N. Astakhova, I. M. Skvortsov, and A. A. Ponomarev, Zh. Obshch. Khim.,34, 2410 (1964).
I. M. Skvortsova and I. V. Antipova, Khim. Geterotsikl. Soedin., No. 6, 764 (1978).
I. M. Skvortsov and L. N. Astakhova, Khim. Geterotsikl. Soedin., No. 2, 147 (1992).
J. M. Patterson, J. Brasch, and P. Drenchko, J. Org. Chem.,27, 1652 (1962).
J. M. Patterson and S. Soedigdo, J. Org. Chem.,32, 2969 (1976).
I. F. Bel'skii, N. I. Shuikin, and G. K. Vasilevskaya, Dokl. Akad. Nauk,136, 491 (1961).
I. F. Bel'skii, I. M. Shuikin, G. K. Vasilevskaya, and G. K. Gaivoronskaya, Izv. Akad. Nauk SSSR. Ser. Khim., No. 9, 1650 (1962).
N. I. Shuikin, I. F. Bel'skii, A. T. Balaban, and K. D. Nenitzescu, Izv. Akad. Nauk SSSR. Ser. Khim., No. 3, 491 (1962).
I. F. Bel'skii, S. N. Khar'kov, and N. I. Shuikin, Dokl. Akad. Nauk,165, 821 (1965).
N. I. Shuikin, I. F. Bel'skii, and S. N. Khar'kov, Izv. Akad. Nauk SSSR. Ser. Khim., 2109 (1967).
É. A. Karakhanov and A. G. Dedov, Catalytic Hydrogenation of Heterocyclic Compounds [in Russian], Izd. MGU, Moscow (1986).
I. F. Bel'skii, F. I. Bel'skii, and V. M. Shostakovskii, Izv. Akad. Nauk SSSR. Ser. Khim., No. 6, 1364 (1977).
I. F. Bel'skii and N. I. Shuikin, Dokl. Akad. Nauk,137, 331 (1961).
I. F. Bel'skii, Zh. Obshch. Khim.,32, 2905 (1962).
I. F. Bel'skii, Izv. Akad. Nauk SSSR. Otd. Khim. Nauk, pp. 493, 1077 (1962).
I. F. Bel'skii, Zh. Obshch. Khim.,32, 2908 (1962).
I. F. Bel'skii, N.I. Shuikin, and G. E. Skobtseva, Izv. Akad. Nauk SSSR. Ser. Khim., pp. 163, 731 (1965).
G. E. Abgaforova, N. I. Shuikin, and I. F. Bel'skii, Izv. Akad. Nauk SSSR. Ser. Khim., No. 4, 734 (1965).
F. Sorm and J. Brandejs, Coll. Czech. Chem. Commun.,12, 444 (1947).
A. A. Ponomarev, A. P. Kriven'ko, and M. V. Noritsina, Dokl. Akad. Nauk,156, 102 (1964).
A. A. Ponomarev, M. V. Noritsina, and A. P. Kriven'ko, Khim. Geterotsikl. Soedin., No. 6, 923 (1966).
A. A. Ponomarev, A. P. Kriven'ko, and M. V. Noritsina, Khim. Geterotsikl. Soedin., No. 5, 850 (1967).
A. A. Ponomarev, A. P. Kriven'ko, and M. V. Noritsina, Inventor's Certificate No. 158,277; Byul. Izobr., No. 21, 15 (1963).
A. A. Ponomarev, M. V. Noritsina, and A. P. Kriven'ko, Inventor's Certificate No. 176,901; Byul. Izobr., No. 24, 22 (1965).
A. A. Ponomarev, A. P. Kriven'ko, and M. V. Noritsina, Khim. Geterotsikl. Soedin., No. 6, 787 (1970).
N. I. Shuikin, A. D. Petrov, V. G. Glukhovtsev, I. F. Bel'skii, and G. E. Skobtsova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 1682 (1964).
A. P. Kriven'ko and T. F. Kotenko, Khim. Geterotsikl. Soedin., No. 12, 1639 (1974).
T. G. Nikolaeva, Chemistry and Technology of Furan Compounds (in Russian], Izd. KPI, Krasnodar (1982) p. 65.
I. N. Klyukova, New Methods of Synthesis and Investigation of Organic Compounds [in Russian], LGU, Leningrad (1979), Part 2, p. 70.
A. P. Kriven'ko, T. G. Nikolaeva, A. A. Espenbetov, Yu. T. Struchkov, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 1, 66 (1985).
USSR Inventor's Certificate 1,049,482; I. N. Klochkova, M. V. Noritsina, and O. Yu. Rastegaev, Byul. Izobr., No. 39, 104 (1983).
M. V. Noritsina, I. N. Klochkova, and T. S. Bykovskaya, Khim. Geterotsikl. Soedin., No. 2, 186 (1976).
V. G. Kharchenko, A. P. Kriven'ko, I. A. Markushina, M. V. Noritsina, T. I. Gubina, G. E. Marinicheva, T. G. Nikolaeva, I. N. Klochkova, and N. V. Shulyakovskaya, Catalytic Reactions in the Liquid Phase. Fifth All-Union Conference on Catalytic Reactions in the Liquid Phase. Fifth All-Union Conference on Catalytic Reactions in the Liquid Phase [in Russian], Alma-Ata (1978), Part 2, p. 92.
N. S. Kozlov, L. I. Moisenok, and S. I. Kozintsev, Dokl. Akad. Nauk,252, 1132 (1980).
N. S. Kozlov, L. P. Dmitriev, and M. I. Kozlyak, Izv. Akad. Nauk BSSR. Ser. Khim.,6, 9 (1977).
S. I. Kozintsev, L. I. Basalaeva, L. V. Gladkikh, and N. S. Kozlov, Khim. Geterotsikl. Soedin., No. 1, 23 (1988).
V. G. Kharchenko, A. P. Kriven'ko, and T. G. Nikolaeva, Inventor's Certificate No. 1,030,359, Byul. Izobr., No. 27, 106 (1983).
V. G. Kharchenko, A. P. Kriven'ko, and T. G. Nikolaeva, Khim. Geterotsikl. Soedin., No. 11, 1561 (1983).
A. P. Kriven'ko, T. G. Nikolaeva, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 4, 435 (1987).
T. G. Nikolaeva and A. P. Kriven'ko, Advances in the Chemistry of Nitrogen-Containing Heterocycles [in Russian], Rostov-on-Don (1983), p. 55.
K. Aso, Bull. Inst. Chem. Res. Tokyo,18, 177 (1939); Chem. Abs.,34, 3273 (1940).
H. Shiff, Ann.,201, 355 (1880).
W. Konig, J. Pract. Chem.,72, 555 (1905).
H. Leditshka, Berichte,85, 483 (1952).
N. Pravdic-Sladovic, Bull. Scien. Concil. Acad. RSFY,8, 142 (1963); R. Zh. Khim, No. 5 (1965).
R. Petit and R. Pallaud, Compt. Rend. Acad. Sci.,258, 230 (1964).
S. I. Burmistrov and V. M. Sannikova, Aspects of Chemistry and Chemical Technologies [in Russian], Khar'kov, No. 54, 20 (1979).
É. Baum, T. E. Goldovskaya, V. G. Kul'nevich, and O. V. Mairova, Khim. Geterotsikl. Soedin., No. 8, 1062 (1981).
D. Weiss and N. Cromwell, J. Heterocycl. Chem.,11, 905 (1974).
J. Blount, D. Coffen, and D. Katonak, J. Org. Chem.,43, 3821 (1978).
W. Reppe, Annalen,596, 117 (1955).
V. G. Kharchenko, I. A. Markushina, T. I. Gubina, and S. P. Voronin, Inventor's Certificate No. 595,961, Byul. Izobr., No. 47, 347 (1980).
V. G. Kharchenko, I. A. Markushina, and T. I. Gubina, Inventor's Certificate No. 677,330; Izobr. SSSR Rubezhom,55, No. 6, 2 (1981).
V. G. Kharchenko, I. A. Markushina, and S. P. Voronin, Inventor's Certificate No. 929,642; Byul. Izobr., No. 19, 100 (1982).
V. G. Kharchenko, I. A. Markushina, and T. I. Gubina, Dokl. Akad. Nauk,255, 1144 (1980).
V. G. Kharchenko, I. A. Markushina, and T. I. Gubina, Zh. Org. Khim.,18, 394 (1982).
T. I. Gubina, V. I. Labunskaya, A. N. Pankratov, S. A. Trushin, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 12, 1614 (1993).
V. G. Kharchenko, S. P. Voronin, T. I. Gubina, I. A. Markushina, and A. F. Oleinik, Khim. Geterotsikl. Soedin., No. 12, 1606 (1984).
V. G. Kharchenko, T. I. Gubina, S. P. Voronin, and I. A. Markushina, Khim. Geterotsikl. Soedin., No. 11, 1453 (1986).
T. I. Gubina, A. A. Rozhnov, S. P. Voronin, V. G. Kul'nevich, S. V. Zhuravlev, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 8, 1046 (1989).
V. G. Kharchenko, T. I. Gubina, and A. A. Rozhnov, Patent No. 1,685,938; Byul. Izobr., No. 39, 97 (1991).
V. G. Kharchenko, I. A. Markushina, T. I. Gubina, and S. P. Voronin, Khim. Geterotsikl. Soedin., No. 2, 219 (1983).
S. P. Voronin, T. I. Gubina, I. A. Markushina, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 10, 1333 (1989).
S. P. Voronin, T. I. Gubina, S. A. Trushin, I. A. Markushina, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 11, 1458 (1989).
N. Clauson-Kaas, F. Limborg, and K. Glens, Acta Chem. Scand.,6, 531 (1952).
N. Elming, Advances in Organic Chemistry [Russian translation], Vol. 2, Mir, Moscow (1964), p. 62.
K. Yu. Novitskii, N. K. Sadovaya, and A. V. Baskina, Khim. Geterotsikl. Soedin., No. 2, 57 (1970).
K. Yu. Novitskii and E. F. Kas'yanova, Khim. Geterotsikl. Soedin., No. 10, 1306 (1970).
P. Nedenskov, N. Elming, J. T. Nielson, and K. Clauson-Kaas, Acta Chem. Scand.,9, 17 (1955).
N. Elming and N. Clauson-Kaas, Acta Chem. Scand.,9, 23 (1955).
A. Josey and E. Jenner, J. Org. Chem.,27, 2466 (1962).
D. Lemal and I. Rave, Tetrahedron,19, 1119 (1963).
R. Epton, Chem. and Ind., No. 10, 425 (1965).
V. I. Shvedov, I. A. Kharizomenova, and A. N. Grinev, Khim. Farm. Zh., No. 4, 594 (1969) [sic].
A. A. Ponomarev, I. A. Markushina, and A. A. Rechinskaya, Khim. Geterotsikl. Soedin., No. 4, 594 (1969) [sic].
I. S. Monakhova and A. V. Malev, Khim. Geterotsikl. Soedin., No. 3, 358 (1975).
E. Garcia Edvard, Org. Prep. Proceed. Int.,6, 11 (1974).
A. Jaeggi Knut, F. Oster Mayer, and H. Schroeter, German Patent No. 2,409,313; Chem. Abs.,82, 85615 (1975).
Hayashi Shoji and Inagaki Keiichi, Chem. Express,1, 572 (1986).
Claude Bernard, Jean Pierre Gagnol, and Patrick Gautier, Inventor's Certificate No. 1,200,849; Chem. Abs.,105, 208759 (1986).
A. D. Abel, D. A. Hoult, and E. J. Jamieson, Tetrahedron Lett.,33, 5831 (1992).
S. Gil Gonzalez, An. R. Acad. Farm.,55, 339 (1989); Chem. Abs.,112, 191731 (1990).
G. Litkei, T. Patonay, and E. Peli, J. Org. Prep. Proceed. Int.,19, 44 (1987).
A. O. Pittet, J. V. Pascale, and D. E. Hruza, U. S. Patent No. 3,980,089; Chem. Abs.,85, 174492 (1976).
A. O. Pittet, J. V. Pascale, and D. E. Hruza, German Patent 2,312,996; Chem. Abs.,80, 14839 (1974).
M. M. Vartanyan, O. L. Eliseev, L. Yu. Brezhnev, and R. A. Karakhanov, Izv. Akad. Nauk SSSR. Ser. Khim., No. 1, 229 (1993).
K. Kondo, M. Suwa, A. Ozaki, and K. Takemoto, J. Electroanal. Chem.,333, 143 (1992).
A. M. Likhosherstov, L. S. Nazarova, V. N. Peresada, and A. P. Skoldinov, Advances in the Chemistry of Nitrogen Containing Heterocycles [in Russian], Rostov-on-Don (1983), p. 93.
W. Hoelderich, M. Hesse, and H. Siegel, European Patent No. 303,206; Chem. Abs.,111, 176725 (1989).
L. Yu. Brezhnev and M. M. Vartanyan, Khim. Geterotsikl. Soedin., No. 9, 1285 (1990).
A. A. Ponomarev, I. A. Markushina, and G. E. Marinicheva, Inventor's Certificate No. 253,806; Byul. Izobr., No. 31, 30 (1969).
G. E. Marinicheva and I. A. Markushina, Chemistry and Technology of Furan Compounds [in Russian], Izd. KPI, Krasnodar (1982), p. 60.
G. E. Marinicheva and I. A. Markushina, Dep. Nauchn. Rab. VINITI, No. 19, 140 (1986).
V. G. Kharchenko, I. A. Markushina, and T. I. Gubina, International Symposium on the Chemistry of Organic Compounds of Sulfur. Abstracts [in Russian], Riga (1980), p. 104.
U. Ohnsorge and H. Koenig, German Patent No. 2,447,252; Ref. Zh. Khim., 2N188 (1977).
K. Yu. Novitskii, N. K. Sadovaya, and A. N. Mentus, Khim. Geterotsikl. Soedin., No. 3, 48 (1971).
A. S. Onishchenko, The Diene Synthesis [in Russian], Izd. Akad. Nauk SSSR, Moscow (1963).
T. Wagner-Jautegg, Synthesis, No. 3, 165 (1980).
E. V. Adamskaya and A. F. Oleinik, Khim. Geterotsikl. Soedin., No. 10, 1299 (1985).
D. W. Jones, J. Chem. Soc. Perkin I, No. 21, 2728 (1972).
Yu. K. Yur'ev and N. S. Zefirov, Zh. Org. Khim.,29, 2954 (1959).
T. J. Kealy, J. Am. Chem. Soc.,84, 966 (1962).
K. N. Zelenin and I. P. Bezhan, Khim. Geterotsikl. Soedin., No. 2, 129 (1970).
C. J. B. Dobbin, D. Mackay, M. R. Penney, and L. H. Dao, J. Chem. Soc. Chem. Commun., No. 20, 703 (1977).
H. Prinzbach, M. Arguelles, and E. Druckrey, Angew. Chem.,78, 1057 (1966).
R. Ziegler, J. Am. Chem. Soc.,91, 446 (1969).
G. O. Schenck and R. Steinmetz, Angew. Chem.,70, 504 (1958).
E. Yoshi, T. Koizumi, E. Kitatsuji, T. Kawazoe, and T. Kaneko, Heterocycles,4, 1663 (1976).
T. L. Gilchrist, Topics in the Chemistry of Heterocyclic Compounds, Bratislava (1981), p. 32.
R. Faragher and T. L. Gilchrist, J. Chem. Soc. Perkin I, No. 1, 258 (1979).
Additional information
Scientific-Research Institute, N. G. Chernyshevskii Saratov State University. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1034–1052, August, 1995. Original article submitted November 24, 1994, revision submitted February 20, 1995.
Rights and permissions
About this article
Cite this article
Gubina, T.I., Kharchenko, V.G. Furan and its derivatives in the synthesis of other heterocycles (review). Chem Heterocycl Compd 31, 900–916 (1995). https://doi.org/10.1007/BF01170318
Issue Date:
DOI: https://doi.org/10.1007/BF01170318