Abstract
Data on the synthesis and chemical properties of the phosphorus-containing derivatives of indoles and pyrroles, published in 1976-1998, are reviewed. The introduction of substituents containing tri- and tetracoordinated phosphorus atom into the heterocycle and the side chain is discussed. Information on the biological activity is presented.
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REFERENCES
R. J. Sundberg, The Chemistry of Indoles, Academic Press, New York, London (1970), p. 489.
W. J. Houlihan, Indoles, Wiley-Interscience, Part 1 (1972), p. 587; Part 2 (1972), p. 615; Part 3 (1979), p. 586.
G. I. Zhungietu, V. A. Budylin, and A. N. Kost, Preparative Chemistry of Indole [in Russian], Shtiintsa, Kishinev (1975), p. 262.
G. I. Zhungietu and M. A. Rekhter, Isatin and its Derivatives [in Russian], Shtiintsa, Kishinev (1977), p. 288.
A. Hofmann, R. Heim, and A. Brack, Helv. Chim. Acta, 42, 1557 (1959).
D. L. J. Hughes, Org. Prep. Proc. Int., 25, 609 (1993).
O. Mingoia, Gazz. Chim. Ital., 60, 144 (1930).
D. Redmore, Chem. Rev., 71, 315 (1971).
A. I. Razumov, P. A. Gurevich, and S. Yu. Baigil'dina, Khim. Geterotsikl. Soedin., 867 (1976).
P. A. Gurevich, V. V. Moskva, and V. V. Kiselev, Advances of Science and Technology. Organic Chemistry [in Russian], VINITI, Moscow, 30, 3 (1993).
T. V. Komina, Thesis for Candidate of Chemical Sciences [in Russian], Kazan (1982).
P. A. Gurevich, A. I. Razumov, T. V. Komina, G. Yu. Klimentova, and T. V. Zykova, Zh. Obshch. Khim., 55, 1257 (1985).
V. V. Moskva, P. A. Gurevitch, T. V. Komina, and A. I. Rasumov, Conf. Internat. de Chimie du Phosphore. Resumes, Nice, France (1983), Abstr. 71.
P. A. Gurevich, V. V. Moskva, T. V. Komina, P. A. Stepanov, V. V. Kiselev, and V. I. Molostov, Advances in the Chemistry of Nitrogen Heterocycles [in Russian], Izd. Rost. Un-ta, Rostov-on-Don (1982), p. 229.
A. I. Razumov, P. A. Gurevich, V. V. Moskva, T. V. Komina, V. V. Kiselev, P. A. Stepanov, and G. Yu. Klimentova, Abstracts of the Seventh All-Union Conference on the Chemistry of Organophosphorus Compounds [in Russian], Leningrad (1982), p. 239.
A. I. Razumov, P. A. Gurevich, S. Yu. Baigil'dina, T. V. Zykova, and R. A. Salakhutdinov, Zh. Obshch. Khim., 44, 2587 (1974).
S. Yu. Baigil'dina, Thesis for Candidate of Chemical Sciences [in Russian], Kazan (1975).
G. Z. Akhmetova, P. A. Gurevich, V. V. Moskva, and V. P. Arkhipov, Zh. Obshch. Khim., 69, 160 (1999).
Z. R. Musabekova, Thesis for Candidate of Chemical Sciences [in Russian], Kazan (1994).
A. M. Kibardin, P. I. Gryaznov, T. Kh. Gazizov, and A. N. Pudovik, Izv. Akad. Nauk SSSR. Ser. Khim., 1826 (1987).
P. A. Gurevich, V. V. Kiselev, V. V. Moskva, S. F. Maksyutova, and T. V. Zykova, Zh. Obshch. Khim., 53, 238 (1983).
P. A. Gurevich, V. V. Kiselev, V. V. Moskva, T. V. Zykova, and S. F. Maksyutova, Zh. Obshch. Khim., 53, 696 (1983).
P. A. Gurevich, V. V. Kiselev, V. V. Moskva, T. V. Zykova, and R. A. Salakhutdinov, Zh. Obshch. Khim., 53, 2145 (1983).
I. Lafaille, F. Mathis, and R. Burgada, Compt. Rend. Acad. Sci., 270C, 1138 (1970).
Z. R. Musabekova, P. A. Gurevich, I. A. Aleksandrova, and T. Kh. Gazizov, Zh. Obshch. Khim., 62, 708 (1992).
D. Purdela and R. Vylchanu, Chemistry of Organophosphorus Compounds [in Russian], Nauka, Moscow (1972), p. 752.
S. B. Khrebtova, L. K. Vasyanina, A. A. Nasarov, M. P. Koroteev, and E. E. Nifant'ev, XI International Conference on the Chemistry of Phosphorus Compounds [in Russian], Kazan (1996), p. 113.
A. A. Tolmachev, S. P. Ivonin, A. V. Kharchenko, and E. S. Kozlov, Zh. Obshch. Khim., 60, 1668 (1990).
B. Bogdan, Phosphorus and Sulfur, 113, 209 (1996).
A. A. Tolmachev, S. P. Ivonin, A. A. Chaikovskaya, T. E. Terekovskaya, S. I. Dovgopoly, and A. N. Kostjuk, XI International Conference on the Chemistry of Phosphorus Compounds [in Russian], Kazan (1996), p. 87.
A. A. Tolmachev, A. V. Kharchenko, and A. D. Mitrokhin, St. Petersburg Meetings, IX International Symposium on the Chemistry of Phosphorus [in Russian], St. Petersburg (1993), p. 96.
A. A. Tolmachev, S. P. Ivonin, A. A. Yurchenko, and E. V. Zarudnitskii, St. Petersburg Meetings 98. Chemistry and Application of Organophosphorus, Organosulfur, and Organosilicon Compounds [in Russian], St. Petersburg (1998), p. 32.
P. A. Stepanov, P. A. Gurevich, A. I. Razumov, and T. V. Zykova, Zh. Obshch. Khim., 61, 86 (1991).
P. A. Gurevich, A. I. Razumov, and P. A. Stepanov, Zh. Obshch. Khim., 52, 1928 (1982).
P. A. Stepanov, Thesis for Candidate of Chemical Sciences [in Russian], Kazan (1983).
A. P. Terent'ev, G. Van-Lun', and M. N. Preobrazhenskaya, Zh. Obshch. Khim., 32, 1335 (1962).
M. N. Preobrazhenskaya, M. F. Fedotova, N. P. Sorokina, O. B. Ogareva, N. V. Uvarova, and N. N. Suvorov, Zh. Obshch. Khim., 34, 1310 (1964).
P. A. Gurevich, P. A. Stepanov, T.V. Zykova, and A. I. Razumov, Zh. Obshch. Khim., 53, 2395 (1983).
G. L. Matevosyan, S. N. Vodovatova, and P. M. Zavlin, Zh. Obshch. Khim., 50, 2803 (1980).
P. A. Gurevich, A. I. Razumov, T. V. Komina, G. Yu. Klimentova, and T. V. Zykova, Zh. Obshch. Khim., 55, 1327 (1985).
P. A. Gurevich, T. V. Komina, G. Yu. Klimentova, T. V. Zykova, and G. I. Ruzal', Khim.-Farm. Zh., 833 (1984).
M. B. Gazizov and R. A. Khairullin, Advances of Science and Technology. Organic Chemistry [in Russian], VINITI, Moscow, 15, 1 (1990).
A. I. Razumov, P. A. Gurevich, S. Kh. Nurtdinov, S. A. Muslimov, and L. M. Tyl'nova, Zh. Obshch. Khim., 47, 1421 (1977).
P. A. Gurevich, Thesis for Doctor of Chemical Sciences [in Russian], Moscow (1985).
G. Z. Akhmetova, P. A. Gurevich, V. V. Moskva, and V. P. Arkhipov, Zh. Obshch. Khim., 68, 2057 (1998).
A. A. Tolmachev, S. O. Ivonin, and A. A. Yurchenko, Phosphorus and Sulfur, 113, 209 (1996).
A. I. Razumov, P. A. Gurevich, and S. A. Muslimov, Zh. Obshch. Khim., 46, 2749 (1976).
A. I. Razumov, P. A. Gurevich, S. A. Muslimov, T. V. Komina, T. V. Zykova, and R. A. Salakhutdinov, Zh. Obshch. Khim., 50, 778 (1980).
S. A. Muslimov, Thesis for Candidate of Chemical Sciences [in Russian], Kazan (1978).
E. S. Batyeva, V. A. Al'fonsov, G. U. Zamaletdinova, and A. N. Pudovik, Zh. Obshch. Khim., 46, 2204 (1976).
B. E. Ivanov and S. V. Samurina, Izv. Akad. Nauk SSSR. Ser. Khim., 2075 (1974).
A. I. Razumov, P. A. Gurevich, and S. A. Muslimov, USSR Inventor's Certificate 614111; Byull. Izobr., No. 25 (1978).
A. I. Razumov, P. A. Gurevich, V. V. Moskva, B. I. Buzykin, T. V. Komina, G. Yu. Klimentova, and P. A. Stepanov, V All-Union Colloquium “Chemistry, Biochemistry, and Pharmacology of Indole Derivatives” [in Russian], Izd. Tbilisskogo Un-ta, Tbilisi (1981), p. 34.
P. A. Gurevich, A. I. Razumov, T. V. Komina, G. Yu. Klimentova, and S. Yu. Baigil'dina, XII Mendeleev Congress on General and Applied Chemistry [in Russian], Nauka, Moscow, No. 4, 214 (1981).
G. F. Smith, Adv. Heterocycl. Chem., 2, 287 (1963).
W. E. Noland and C. F. Hammer, J. Org. Chem., 25, 1525 (1960).
O. Schmitz, Ber., 63, 323 (1930).
J. I. G. Cadogan, D. J. Sears, and D. M. Smith, J. Chem. Soc. C, 1314 (1969).
F. Troxler, F. Seemann, and A. Hofmann, Helv. Chim. Acta, 42, 2073 (1959).
L. M. Morozovskaya, M. A. Kolesnikova, and N. N. Suvorov, Zh. Obshch. Khim., 38, 2788 (1968).
H. Timmler, Ger. Offen 2030508; Chem. Abstr., 76, 85920 (1972).
G. Z. Akhmetova, P. A. Gurevich, V. V. Moskva, and V. P. Arkhipov, Zh. Obshch. Khim., 68, 2055 (1998).
E. F. Janson and E. K. Fields, J. Org. Chem., 27, 402 (1962).
E. A. Torralba and T. C. Myers, J. Org. Chem., 22, 972 (1957).
N. F. Albertson, US Patent 2980692; Chem. Abstr., 56, 457 (1962).
J. Szmuszkoviez, J. Am. Chem. Soc., 80, 3782 (1958).
H. Hellman and O. Schumacher, Ann., 640, 79 (1961).
J. A. Enkhoorn, S. Silva, D. Osmund, and V. Snieckus, Can. J. Chem., 5, 792 (1973).
A. Chakh and K. Kel'ner, Chemistry and Application of Organophosphorus Compounds [in Russian], Nauka, Moscow (1974), p. 184.
P. I. Yagodinets, I. N. Chernyuk, E. M. Volynskaya, I. I. Shevchuk, and V. N. Kushnir, Zh. Obshch. Khim., 54, 772, (1984).
D. Magarathnam and P. C. Srinivasan, Synthesis, 926 (1982).
H. Fischer and G. Ort, Chemistry of Pyrrole [Russian translation], ONTI, Leningrad (1937), p. 122.
A. Arcoria, S. Fisichella, E. Maccarone, and G. Scarlata, J. Heterocycl. Chem., 12, 215 (1975).
D. Kh. Yarmukhametova, B. V. Kudryavtsev, and L. I. Anpilova, Izv. Akad. Nauk SSSR. Ser. Khim., 435 (1974).
I. A. Tovannidis, Phosphorus and Sulfur, 12, 249 (1982).
G. I. Zhungietu, F. N. Chukhrai, and A. I. Tolmachev, Zh. Vses. Khim. Obshch. D. I. Mendeleeva, 15, 590 (1970).
G. Z. Akhmetova, V. V. Moskva, P. A. Gurevich, and V. P. Arkhipov, Zh. Obshch. Khim., 67, 1212 (1997).
A. Mustafa, M. M. Sidky, and F. M. Soliman, Tetrahedron, 22, 393 (1966).
Kh. I. Riisalu, V. V. Vasil'ev, and B. I. Ionin, Zh. Obshch. Khim., 54, 563 (1984).
M. R. H. Mahran, M. D. Khidre, and W. M. Abdou, Phosphorus, Sulfur, Silicon, Relat. Elem., 101, 17 (1995).
E. E. Nifant'ev, T. S. Kukareva, and O. V. Davydochkina, IV Conference “Bioantioxidant” [in Russian], Moscow, 1, 207 (1993).
P. A. Gurevich, G. Z. Akhmetova, A. T. Gubaidullin, V. V. Moskva, and I. A. Litvinov, Zh. Obshch. Khim., 68, 1570 (1998).
G. Z. Akhmetova, Thesis for Candidate of Chemical Sciences [in Russian], Kazan (1998).
A. N. Pudovik and I. V. Gur'yanova, Chemistry and Application of Organophosphorus Compounds. Proceedings of IV Conference [in Russian], Nauka, Moscow (1972), p. 164.
A. I. Razumov, P. A. Gurevich, and S. Yu. Baigil'dina, Zh. Obshch. Khim., 44, 2586 (1974).
A. I. Razumov, P. A. Gurevich, and S. Yu. Baigil'dina, USSR Inventor's Certificate 422740; Byull. Izobr., No. 13 (1974).
Yu. E. Utkin, A. S. Sergeeva, V. N. Tarasov, V. K. Promonenkov, and S. V. Ivin, Zh. Obshch. Khim., 37, 2710 (1967).
P. A. Gurevich, V. V. Kiselev, V. V. Moskva, and G. I. Ruzal', Khim.-Farm. Zh., 51 (1983).
G. E. Lathourakis and K. E. Litinas, J. Chem. Soc. Perkin Trans. 1, 491 (1996).
G. Z. Akhmetova, P. A. Gurevich, V. V. Moskva, N. V. Kokhan, and V. P. Arkhipov, Zh. Obshch. Khim., 67, 877 (1997).
A. N. Pudovik, I. V. Gur'yanova, and E. A. Ishmaeva, Reactions and methods of Investigation of Organic Compounds [in Russian], Khimiya, Moscow, 19, 59 (1968).
E. E. Nifant'ev, Chemistry of Hydrophosphoryl Compounds [in Russian], Nauka, Moscow (1983), p. 78.
H. Gross, L. Brennecke, and B. Costisella, J. Prakt. Chem., 318, 277 (1976).
B. A. Arbuzov, E. N. Dianova, A. V. Fuzhenkova, and A. F. Lisin, Izv. Akad. Nauk SSSR. Ser. Khim., 1825 (1975).
S. V. Fridland, L. B. Kashevarova, and L. V. Ryapisova, XI International Conference on Chemistry of Phosphorus Compounds [in Russian], Kazan (1996), p. 139.
L. V. Ryapisova, L. B. Kashevarova, I. G. Shaikhiev, and S. V. Fridland, Zh. Obshch. Khim., 67, 2061 (1997).
E. N. Koz'minykh, E. S. Berezina, and V. O. Koz'minykh, Zh. Obshch. Khim., 66, 1128 (1996).
A. A. Sobanov, A. V. Zolotukhin, and V. I. Galkin, Abstracts of Conference in Memory of I. M. Shermergorn [in Russian], Kazan (1996), p. 46.
A. I. Razumov, P. A. Gurevich, and S. Yu. Baigil'dina, USSR Inventor's Certificate 437771; Byull. Izobr., No. 28 (1974).
A. I. Razumov, P. A. Gurevich, S. Yu. Baigil'dina, and M. V. Alparova, Zh. Obshch. Khim., 44, 2585 (1974).
A. I. Razumov, P. A. Gurevich, R. I. Tarasova, and S. Yu. Bail'gildina, Zh. Obshch. Khim., 46, 33 (1976).
N. V. Kolotilo, P. P. Onysko, and A. A. Sinitsa, Zh. Obshch. Khim., 65, 1221 (1995).
A. I. Razumov, P. A. Gurevich, G. I. Ruzal', S. Yu. Baigil'dina, and S. A. Muslimov, Kazan; Dep. TsNIINTI, No. DR-169 (1980).
E. A. Muzafarova, G. Z. Akhmetova, P. A. Gurevich, and V. V. Moskva, Zh. Obshch. Khim., 66, 523 (1996).
P. A. Gurevich, V. V. Moskva, G. Z. Akhmetova, and E. Muzafarova, All-Russian Conference Chemistry of Organophosphorus Compounds and Prospects for their Development at the Threshold of the XXI Century [in Russian], Moscow (1998), p. 47.
P. A. Gurevich, V. V. Moskva, G. Yu. Klimentova, V. V. Kiselev, Kazan; Dep. NIITEKHIM, No. 207-khp-87 (1987).
P. A. Gurevich, V. V. Kiselev, V. V. Moskva, and N. A. Moskva, Zh. Obshch. Khim., 54, 471 (1984).
P. A. Gurevich, G. Yu. Klimentova, V. V. Moskva, T. V. Zykova, F. Sh. Shagvaleev, and V. V. Kiselev, Zh. Obshch. Khim., 57, 2316 (1987).
B. S. Drach and E. P. Sviridov, Zh. Obshch. Khim., 43, 1648 (1973).
P. A. Gurevich, V. V. Moskva, V. V. Kiselev, and G. Yu. Klimentova, VIII All-Union Conference on the Chemistry of Organophosphorus Compounds, dedicated to the 80th Anniversary of the Arbuzov Reaction [in Russian], Kazan (1985), p. 9.
M. R. Gratchev, G. I. Kurochkina, V. V. Negrebetsky, Phosphorus, Sulfur, Silicon, Relat. Elem., 88, 257 (1994).
Q. Mingoia, Gazz. Chim. Ital., 62, 333 (1932).
A. I. Razumov, P. A. Gurevich, and S. Yu. Baigil'dina, USSR Inventor's Certificate 458558; Byull. Izobr., No. 4 (1975).
B. A. Khaskin, Reactions and Methods of Investigation of Organic Compounds [in Russian], Khimiya, Moscow, 20, 129 (1969).
G. I. Ruzal', A. I. Razumov, P. A. Gurevich, and S. A. Muslimov, Aspects of Epidemiology and Applied Immunology [in Russian], Leningrad, 3, 24 (1977).
P. A. Gurevich, A. I. Razumov, S. A. Muslimov, T. V. Komina, S. Yu. Baigil'dina, T. V. Zykova, and R. A. Salakhutdinov, Advances in the Chemistry of Nitrogen-Containing Heterocycles [in Russian], Zinatne, Riga, 2, 28 (1979).
V. G. Rozinov, G. A. Pensionerova, L. V. Izhboldina, V. I. Donskikh, V. E. Kolbina, A. I. Mikhaleva, and K. E. Korostova, VII All-Union Conference on the Chemistry of Organophosphorus Compounds [in Russian], Kazan (1982), p. 147.
V. G. Rozinov, G. A. Pensionerova, V. I. Donskikh, L. M. Sergienko, O. V. Petrova, A. V. Kalabina, and A. I. Mikhaleva, Zh. Obshch. Khim., 54, 2241 (1984).
G. A. Pensionerova, V. G. Rozinov, A. V. Kalabina, V. I. Donskikh, G. V. Ratovskii, and M. Yu. Dmitrichenko, Zh. Obshch. Khim., 52, 2491 (1982).
L. N. Harris, Tetrahedron Lett., 4465 (1966).
V. G. Rozinov, L. V. Izhboldina, G. A. Pensionerova, L. M. Sergeenko, V. I. Donskikh, S. F. Malysheva, N. G. Glukhikh, and G. V. Ratovskii, Zh. Obshch. Khim., 54, 1051 (1984).
R. S. Greenley, M. L. Nielsen, and L. Parts, J. Org. Chem., 29, 1009 (1964).
J. J. Pappas, and E. Gancher, J. Heterocycl. Chem., 86, 265 (1969).
S. Hunig and H. Steinmetzer, Tetrahedron Lett., 643 (1972).
H. Tolkmith, E. C. Britton, and C. F. Holoway, US Patent 2802823; Chem. Abstr., 52, 2065 (1958).
H. Tolkmith, E. C. Britton, and C. F. Holoway, US Patent 2802824; Chem. Abstr., 52, 2083 (1958).
S. R. Wilson and M. F. Price, Synth. Commun., 12, 657 (1982).
T. Koizumi, V. Kobayashi, H. Amitani, and A. Voshii, J. Org. Chem., 42, 3459 (1977).
A. F. Grapov, L. V. Razvodskaya, and N. N. Mel'nikov, Chemistry and Application of Organophosphorus Compounds. Proceedings of V All-Union Conference [in Russian], Nauka, Moscow (1974), p. 254.
H. Pohlemann, H. Schroeder, H. Stummeyer, and H. Adolphi, US Patent 2865912; Chem. Abstr., 53, 11420 (1959).
N. P. Grechkin and L. N. Grishina, Zh. Obshch. Khim., 48, 2203 (1978).
N. P. Grechkin and L. N. Grishina, Zh. Obshch. Khim., 52, 1113 (1982).
L. N. Grishina, G. A. Kashafutdinov, and N. P. Grechkin, Zh. Obshch. Khim., 48, 558 (1978).
M. C. J. Hewson and R. Schmutzler, Phosphorus and Sulfur, No. 8, 9 (1980).
R. Schmutzler, Angew. Chem., 76, 893 (1964).
A. F. Grapov, L. V. Razvodskaya, and N. N. Mel'nikov, Zh. Obshch. Khim., 44, 281 (1974).
K. Issleib and K. P. Dopfe, Z. Chem., 22, 215 (1982).
B. Marianne, J. Xian-Yun, and W. Halina, Synthesis, 1074 (1995).
N.P. Chizhov and F. S. Noskov, Abstracts of Conference of the Military Medical Academy [in Russian], Leningrad (1972), p. 116.
A. N. Grinev, Khim.-Farm. Zh., No. 5, 6 (1970).
N. V. Khromov-Borisov, L. S. Efros, and A. B. Tomchin, Zh. Obshch. Khim., 44, 1641 (1974).
P. A. Gurevich, A. I. Razumov, S. A. Muslimov, T. V. Komina, and R. L. Yafarova, Kazan, Dep TsNIINTI, No. DR-170 (1980).
A. I. Razumov, P. A. Gurevich, and L. A. Monakhova, USSR Inventor's Certificate 362025; Byull. Izobr., No. 2, (1973).
I. V. Zakonnikova, A. V. Val'dman, M. M. Kozlovskaya, and G. F. Rzhevskaya, Farmakologiya i Toksikologiya, No. 4, 6 (1980).
A. I. Razumov, P. A. Gurevich, S. A. Muslimov, and V. G. Usacheva, Zh. Obshch. Khim., 46, 2381 (1976).
A. I. Razumov, D. Kh. Yarmukhametova, P. A. Gurevich, B. V. Kudryavtsev, and S. A. Muslimov, Zh. Obshch. Khim., 48, 228 (1978).
P. A. Gurevich, A. I. Razumov, S. A. Muslimov, and G. Yu. Klimentova, Kazan, Dep. NIITEKHIM, No. 687-khp-D82 (1982).
A. N. Pudovik and G. E. Yastrebova, Usp. Khim., 39, 1190 (1970).
A. N. Pudovik, A. M. Shakirova, and V. I. Nikitina, Dokl. Akad. Nauk, 182, 1338 (1968).
S. F. Chen, S. D. Kumar, and M. Tishler, Tetrahedron Lett., 49, 5461 (1983).
P. A. Gurevich, S. Yu. Baigil'dina, L. F. Mal'tseva, and G. I. Ruzal', Kazan, Dep. NIITEKHIM, No. 49khp-85Dep. (1985).
P. A. Gurevich, T. V. Komina, and G. Yu. Klimentova, Zh. Obshch. Khim., 54, 2199 (1984).
M. N. Preobrazhenskaya, K. B. Kholodkovskaya, E. G. Balashova, and N. N. Suvorov, Khim. Geterotsikl. Soedin., Zinatne, Riga, Collection 1, 28 (1967).
A. I. Razumov, P. A. Gurevich, B. V. Kudryavtsev, and S. Yu. Baigil'dina, Zh. Obshch. Khim., 47, 2538 (1977).
I. L. Vladimirova, A. F. Grapov, and V. I. Lomakina, Reactions and Methods of Investigation of Organic Compounds [in Russian], Khimiya, Moscow, 16, 24 (1966).
L. I. Volovel'skii, S. Yu. Baigil'dina, P. A. Gurevich, and N. V. Popova, USSR Inventor's Certificate 488813; Byull. Izobr., No. 39 (1975).
P. M. Zavlin, Chemistry and Application of Organophosphorus Compounds. Proceedings of IV Conference [in Russian], Nauka, Moscow (1972), p. 134.
N. N. Suvorov and V. S. Shashkov, Chemistry and Pharmacology of Agents for Treatment of Radiation Sickness [in Russian], Atomizdat, Moscow (1975), p. 39.
P. A. Gurevich, A. I. Razumov, and P. A. Stepanov, Zh. Obshch. Khim., 53, 941 (1983).
K. V. Vatsuro and G. L. Mishchenko, Named Reactions in Organic Chemistry [in Russian], Khimiya, Moscow (1976), p. 528.
M. Somei, T. Hasegawa, and S. Kaneco, Heterocycles, 10, 1983 (1983).
V. I. Shvedov, E. K. Panisheva, T. F. Vlasova, and A. N. Grinev, Khim. Geterotsikl. Soedin., 1354 (1973).
S. A. Monti and W. O. Johnson, Tetrahedron, 26, 3685 (1970).
A. K. Sheinkman, Khim. Geterotsikl. Soedin., 3 (1974).
A. K. Sheinkman, G. V. Samoilenko, S. N. Baranov, and P. A. Gurevich, USSR Inventor's Certificate 407900; Byull. Izobr., No. 47 (1973).
G. V. Samoilenko and P. A. Gurevich, Symposium II on the Chemistry and Technology of Heterocyclic Compounds from Mineral Fuels [in Russian], Donetsk (1973), p. 10.
A. K. Sheinkman, G. V. Samoilenko, S. N. Baranov, P. A. Gurevich, and A. N. Prilepskaya, IV All-Union Colloquium Chemistry and Pharmacology of Indole Compounds [in Russian], Shtiintsa, Kishinev (1975), p. 71.
A. K. Sheinkman, G. V. Samoilenko, and S. N. Baranov, Chemistry and Application of Organophosphorus Compounds [in Russian], Nauka, Moscow (1974), p. 366.
R. T. Brown, J. A. Jouli, and P. G. Samms, General Organic Chemistry, Vol. 8, Khimiya, Moscow (1985), p. 488.
N. N. Suvorov, V. P. Mamaev, and V. M. Rodionov, Reactions and Methods of Investigation of Organic Compounds [in Russian], Khimiya, Moscow, 9, 21 (1959).
I. I. Grandberg and V. I. Sorokin, Usp. Khim., 43, 266 (1974).
A. E. Arbuzov and V. M. Tikhvinskii, in: A. E. Arbuzov, Selected Works on the Chemistry of Organophosphorus Compounds [in Russian], Nauka, Moscow (1976).
M. J. Gallagher and F. G. Mann, J. Chem. Soc., 4855 (1963).
K. C. Srivastava and K. D. Berlin, J. Org. Chem., 37, 4487 (1972).
K. Issleib, R. Wolff, and M. Lengies, J. Prakt. Chem., 318, 207 (1976).
A. I. Razumov, B. G. Liorber, V. V. Moskva, and M. P. Sokolov, Usp. Khim., 1199 (1973).
A. I. Razumov and P. A. Gurevich, USSR Inventor's Certificate 172796; Byull. Izobr., No. 14 (1965).
A. I. Razumov and P. A. Gurevich, Zh. Obshch. Khim., 37, 1615 (1967).
A. I. Razumov and P. A. Gurevich, Trudy Kazanskogo Khim.-Tekhnol. In-ta, 36, 480 (1967).
E. Fischer and T. Schmidt, Ber., 21, 1811 (1888).
V. A. Budylin, A. N. Kost, and E. D. Matveeva, Khim. Geterotsikl. Soedin., 55 (1972).
B. Miller and E. R. Matjeka, J. Am. Chem. Soc., 102, 4772 (1980).
J. Xian-Yun, X. Fa-Gao, C. Wan-Yi, and Hu Bing-Fang, Chin. J. Org. Chem., 59, 622 (1994).
A. Coutere, E. Deniau, Y. Gimbert, and P. Graddaudon, Tetrahedron, 49, 1431 (1993).
P. A. Gurevich, A. I. Razumov, R. L. Yafarova, T. V. Komina, and F. Kh. Kutumova, Zh. Obshch. Khim., 51, 1671 (1981).
P. A. Gurevich, Kazan, Dep. NIITEKHIM, No. 54-khp-85Dep. (1985).
Yu. P. Kitaev and B. I. Buzykin, Hydrazones [in Russian], Nauka, Moscow (1974), p. 257.
C. Y. Yuan, C. Z. Li, and G. H. Wang, Phosphorus, Sulfur, Silicon, Relat. Elem., 75, 147 (1993).
P. A. Gurevich, P. A. Stepanov, and A. I. Razumov, Zh. Obshch. Khim., 53, 2394 (1983).
E. N. Dolzhnikova, E. N. Tsvetkov, G. S. Petrova, R. V. Poponova, and B. V. Zhdanov, Zh. Obshch. Khim., 48, 525 (1978).
H. N. Rydon and S. Siddappa, J. Chem. Soc., 2462 (1951).
M. R. Tirakyan, G. A. Panosyan, and Yu. M. Dagnyan, Zh. Obshch. Khim., 62, 2684 (1992).
A. A. Tolmachev, Thesis for Candidate of Chemical Sciences [in Russian], Kiev (1986).
N. A. Polezhaeva, P. G. Sakhibullina, T. G. Kostyunina, A. V. Prosvirkin, N. I. Tiryshkin, and G. A. Chmutova, Zh. Obshch. Khim., 66, 1134 (1996).
A. V. Prosvirkin, N. A. Polezhaeva, G. A. Chmutova, and V. G. Sakhibullina, Chemistry and Application of Organophosphorus, Organosulfur, and Organosilicon Compounds. St. Petersburg Meetings 98, St. Petersburg (1998), p. 276.
B. A. Trofimov and A. I. Mikhaleva, N-Vinylpyrroles [in Russian], Nauka, Novosibirsk (1984), p. 262.
L. N. Yakhontov and R. G. Glushkov, Synthetic Medicinal Substances [in Russian], Meditsina, Moscow (1983), p. 272.
T. V. Moskovkina, Zh. Org. Khim., 33, 138 (1997).
M. N. Preobrazhenskaya, Usp. Khim., 36, 1760 (1967).
T. V. Golovko, N. P. Solov'eva, and V. G. Granik, Mendeleev Commun., No. 5, 191 (1995).
G. V. Ratovskii, S. L. Belaya, A. A. Tolmachev, and A. N. Kostyuk, Zh. Obshch. Khim., 62, 2046 (1992).
G. I. Zhungietu and G. N. Dorofeenko, Usp. Khim., 41, 1627 (1972).
N. N. Suvorov, Zh. Vses. Khim. Obshch. D. I. Mendeleeva, 21, 144 (1976).
B. Pullman and A. Pullman, Quantum Biochemistry [Russian translation], Mir, Moscow (1965), p. 654.
A. Sent-D'erd'i, Introduction to Submolecular Biology, Nauka, Moscow (1964), p. 139.
D. F. Downing, Quart. Rev., 16, 133 (1962).
N. N. Yarovenko, Zh. Vses. Khim. Obshch. D. I. Mendeleeva, 4, 448 (1964).
B. G. van den Bos, C. J. Schoot, M. J. Koopmans, and J. Meltzer, Rec. Trav. Chim., 80, 1040 (1961).
J. Meltzer, K. Wellinda, and B. G. van den Boss, US Patent 3111525; Chem. Abstr., 60, 9285 (1964).
C. van den Mestering and H. Veldstra, Rec. Trav. Chim., 77, 1096 (1958).
V. P. Shamshin, V. F. Shner, and N. N. Suvorov, Khim. Geterotsikl. Soedin., 498 (1972).
N. N. Suvorov, V. A. Chernov, L. M. Morozovskaya, and S. M. Volodarskaya, USSR Inventor's Certificate 168294; Byull. Izobr., No. 4 (1965).
L. M. Morozovskaya, N. N. Suvorov, M. A. Kolesnikova, V. A. Chernov, and S. M. Volodarskaya, Chemistry of Organic Compounds of Phosphorus [in Russian], Nauka, Leningrad (1967), p. 223.
K. C. Tsou, H. C. F. Su, D. Rabiger, H. Heymann, and A. M. Seligman, J. Med. Chem., 10, 662 (1967).
J. P. Horwitz, C. V. Easwaran, and P. L. Volf, Biochim. Biophys. Acta (E), 276, 206 (1972).
S. Umezawa, K. Tatsuta, O. Izawa, and T. Tsuchija, Tetrahedron Lett., 97 (1972).
V. N. Konyukhov, T. A. Bandurina, G. M. Anoshina, and Z. V. Pushkareva, Chemotherapy of Tumors in the USSR [in Russian], Sb. Ural'skogo Politekhn. In-ta, No. 25-26, 45 (1978).
T. A. Bandurina, V. N. Konyukhov, and A. A. Koltysheva, Chemotherapy of Tumors in the USSR [in Russian], Sb. Ural'skogo Politekhn. In-ta, No. 31, 160 (1980).
U. Katsuko, I. Shiro, and A. Sanya, Chem. Pharm. Bull., 22, 1918 (1974).
A. Burger and H. Shelver, J. Med. Pharm. Chem., 4, 225 (1961).
H. Pohlemann and R. Windels, British Patent 869339; Chem. Abstr., 56, 10104 (1962).
N. P. Grechkin, L. N. Grishina, I. D. Neklesova, M. A. Kudrina, and N. N. Anisimova, USSR Inventor's Certificate 430102; Byull. Izobr., No. 20 (1974).
N. P. Grechkin, L. N. Grishina, and G. A. Kashafutdinov, USSR Inventor's Certificate 524803; Byull. Izobr., No. 30 (1976).
N. P. Grechkin and L. N. Grishina, Izv. Akad. Nauk SSSR. Ser. Khim., 1670 (1973).
N. P. Grechkin and L. N. Grishina, Izv. Akad. Nauk SSSR. Ser. Khim., 1898 (1974).
N. P. Grechkin, L. N. Grishina, I. D. Neklesova, M. A. Kudrina, and N. N. Anisimova, USSR Inventor's Certificate 433152; Byull. Izobr., No. 23 (1974).
P. A. Gurevich, S. Yu. Baigil'dina, and G. I. Ruzal', Kazan, Dep. NIITEKHIM, No. 51-khp-85Dep. (1985).
P. A. Gurevich, A. I. Razumov, V. V. Moskva, T. V. Komina, G. Yu. Klimentova, and V. V. Kiselev, Abstracts of All-Union Conference of Chemical Means for the Protection of Plants [in Russian], Ufa (1982), p. 17.
Y. Jin and G. Just, Tetrahedron Lett., 39, 6433 (1998).
R. K. Sharma, S. S. Kohle, and R. S. Tripathi, Indian J. Agron., 39, 479 (1994).
S. P. Ivonin, A. A. Tolmachev, T. E. Terikovska, and A. M. Pinchuk, XII International Conference on Chemistry of Phosphorus Compounds [in Russian], Kiev (1999), p. 73.
A. A. Tolmachev and A. M. Pinchuk, XII International Conference on Chemistry of Phosphorus Compounds [in Russian], Kiev (1999), p. 138.
T. A. Bandurina, V. N. Konyukhov, and A. A. Koltysheva, Chemotherapy of Tumors in the USSR [in Russian], Sb. Ural'skogo Politekhn. In-ta, No. 36, 105 (1982).
G. L. Matevosyan and P. M. Zavlin, Zh. Obshch. Khim., 68, 1536 (1998).
I. V. Galkina, É. R. Zvereva, V. I. Galkin, A. A. Sobanov, and R. A. Cherkasov, Zh. Obshch. Khim., 68, 1453 (1998).
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Gurevich, P.A., Yaroshevskaya, V.A. Phosphorus-containing Derivatives of Indole and Pyrrole. (Review). Chemistry of Heterocyclic Compounds 36, 1361–1401 (2000). https://doi.org/10.1023/A:1017562111215
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DOI: https://doi.org/10.1023/A:1017562111215