Abstract
The literature from the last 15–20 years on the synthesis of heteroatomic pyridine derivatives through the formation of pyridine carbon-heteroatom bonds is reviewed.
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References
M. A. Yurovskaya, O. D. Mit'kin, and F. V. Zaitseva,Khim. Geterotsikl. Soedin., No. 8, 1013 (1998).
S. L. Taylor, D. Y. Lee, and J. C. Martin,J. Org. Chem.,48, 4156 (1983).
D. Comis and N. B. Mantlo,Tetrahedron Lett.,24, 3683 (1983).
Y. Hamamoto and A. Yanagi,Heterocycles,19, 41 (1982).
Y. Yamamoto and A. Yanagi,Chem. Pharm. Bull.,30, 2003 (1982).
Y. Yamamoto, T. Tanaka, H. Ouchi, M. Miyakawa, and Y. Morita,Heterocycles,41, 817 (1995).
E. Ya. Lukevics and I. D. Segal, Preprint. Parts 1 (63 pp.) and 2 (70 pp.), Institute of Organic Synthesis, Latvian SSR Academy of Sciences, Riga (1986).
E. Ya. Lukevics and I.D. Segal,Khim. Geterotsikl. Soedin., No. 1, 5 (1987).
E. Lukevics and I. D. Segal, in:Organic Chemistry Reviews, G. Davies et al. (eds.), J. Organomet. Chem. Library, Vol. 20, Elsevier, Amsterdam etc. (1988), p. 69.
J. Verbeek, A. V. E. George, R. L. P. De Jong, and L. V. Brandsma,J. Chem. Soc., Chem. Commun., No. 4, 257 (1984).
A. G. M. Barrett, D. Dauzonne, I. A. O'Neil, and A. Renaud,J. Org. Chem.,49, 4409 (1984).
F. Marsais, F. Trecourt, P. Breant, and G. Queguiner,J. Heterocycl. Chem.,25, 81 (1988).
D. Comis and Y. Ch. Myoung,J. Org. Chem.,55, 292 (1990).
M. Zeldin and J.-M. Xu,J. Organomet. Chem.,320, 267 (1987).
F. Trecourt, M. Mallet, F. Marsais, and G. Queguiner,J. Org. Chem.,53, 1367 (1988).
N. Furakawa, T. Shibutani, and H. Fujihara,Tetrahedron Lett.,30, 7091 (1989).
C. Quesnelle, T. Iihama, T. Aubert, H. Perrier, and V. Snieckus,Tetrahedron Lett.,33, 2625 (1992).
A. R. Katritzky, J. M. Aurrecoechea, and L. M. Vazquez de Miguel,Heterocycles,26, 427 (1987).
M. Tsukazaki and V. Snieckus,Heterocycles,35, 689 (1993).
S. G. Davies and M. R. Shipton,J. Chem. Soc. Perkin Trans. 1, No. 3, 501 (1991).
S. G. Ang and W. L. Kwik,J. Organomet. Chem.,361, 27 (1989).
P. Jutzi and U. Gilge,J. Organomet. Chem.,246, 163 (1983).
A. Shih-Yuan and W.-C. Dai,Tetrahedron Lett.,37, 495 (1996).
Y. Yamamoto and A. Yanagi,Heterocycles,16, 1161 (1981).
F. Friedel,Ber.,45, 428 (1912).
H. Suzuki, T. Murashima, and K. Tsukamoto, Jpn. Pat. 04282368;Chem. Abstr.,108, 101821 (1988).
H. Suzuki, I. Kozai, and T. Murashima,J. Chem. Res., Synop., No. 4, 156 (1993).
H. Suzuki, M. Iwaya, and T. Mori,Tetrahedron Lett.,38, 5647 (1997).
J. M. Bakke, I. Hegbom, E. Overleide, and K. Aaby,Acta Chem. Scand.,48, 1001 (1994).
J. M. Bakke and E. Rames,Synthesis, No. 3, 281 (1997).
J. M. Bakke, E. Ranes, J. Rina, and H. Svensen, in:Abstracts of the 7th Blue Danube Symposium on Heterocyclic Chemistry, Eger, Hungary (1998), PO7.
W. Orth and W. Fickert, Ger. Offen. Pat. 3308449;Chem. Abstr.,101, 23354 (1984).
T. Clausen and E. Konrad, Ger. Offen. Pat. 3706565;Chem. Abstr.,110, 13383 (1989).
H. Ritter and H. H. Licht,J. Heterocycl. Chem.,32, 585 (1995).
J. Loreno and Z. Talik,Pr. Nauk Akad. Ekon. im. Oskara Langego Wroclawiu,313, 131 (1985);Chem. Abstr.,107, 84354 (1986).
T. Talik and Z. Talik,Pr. Nauk Akad. Ekon. im. Oskara Langego Wroclawiu,313, 121 (1985);Chem. Abstr.,106, 84353 (1987).
M. Wandas and T. Talik,Pr. Nauk Akad. Ekon. im. Oskara Langego Wroclawiu,435, 129 (1988);Chem. Abstr.,112, 178598 (1990).
B. Palasek and T. Talik,Pr. Nauk Akad. Ekon. im. Oskara Langego Wroclawiu,435, 119 (1988);Chem. Abstr.,112, 178597 (1990).
I. F. Falyakhov, R. Z. Gil'manov, G. P. Sharnin, and T. G. Bol'shakova,Khim. Geterotsikl. Soedin., No. 7, 958 (1998).
T. Talik and Z. Talik,Pr. Nauk Akad. Ekon. im. Oskara Langego Wroclawiu,313, 115 (1985);Chem. Abstr.,106, 82352 (1987).
A. Puszko,Pr. Nauk Akad. Ekon. im. Oskara Langego Wroclawiu,278, 169 (1984);Chem. Abstr.,103, 104819 (1985).
A. N. Osman and M. Khalifa,Egypt. J. Chem.,27, 705 (1985).
W. Hallenbach and H. Lindel, Ger. Offen. Pat. 3707361;Chem. Abstr.,113, 38900 (1990).
A. A. Nazibulin and M. V. Klyuev,Zh. Org. Khim.,31, 1068 (1995).
M. Malinowski and I. Kaczmarek, Pol. Pat. 149751;Chem. Abstr.,113, 230409 (1990).
M. Malinowski,Bull. Soc. Chim. Belg.,97, 51 (1988).
G. L. Rusinov, I. E. Filatov, and K. I. Pashkevich,Izv. Ross. Akad. Nauk, Ser. Khim., No. 2, 365 (1993).
L. Kaczmarek, R. Balicki, and M. Malinowski,J. Prakt. Chem.,332, 423 (1990).
C. K. McGill and J. J. Sutor, U.S. Pat. 4386209;Chem. Abstr.,100, 6343 (1984).
Reilly Tar and Chem. Corp., Jpn. Pat. 58208266;Chem. Abstr.,100, 120901 (1984).
C. K. McGill and T. D. Bailey, U.S. Pat. 4405790;Chem. Abstr.,100, 22584 (1984).
S. Enomoto and H. Kashiwagi, Jpn. Rat. 7995576;Chem. Abstr.,92, 6424 (1980).
H. Kashiwagi and S. Enomoto,Yakugaku Zasshi,100, 140 (1980);Chem. Abstr.,93, 25483 (1980).
D. J. Buurman and H. C. van der Plas,J. Heterocycl. Chem.,23, 1015 (1986).
R. A. Hollins, L. H. Merwin, R. A. Nissan, W. S. Wilson, and R. Gilardi,J. Heterocycl. Chem.,33, 895 (1996).
F. E. Janssens, G. S. M. Diels, J. L. G. Torremans, and F. M. Sommen, Eur. Pat. 282133;Chem. Abstr.,110, 75503 (1989).
A.-G. Degussa, Belg. Pat. 890331;Chem. Abstr.,97, 6159 (1982).
Koei Kagaku Kogyo K. K., Jpn. Pat. 8265756;Chem. Abstr.,97, 111294 (1982).
P. C. Jain and N. Anand, Ind. Pat. 101837;Chem. Abstr.,92, 76552 (1979).
W. G. Lobeck, Jr., J. S. New, and J. P. Yevich, Ger. Offen. Pat. 3601143;Chem. Abstr.,105, 172510 (1986).
K. Matsumoto, H. Minatogawa, M. Munakata, M. Toda, and H. Tsukube,Tetrahedron Lett.,31, 3923 (1990).
A. M. Sipyagin and V. G. Kartsev,Zh. Org. Khim.,23, 2187 (1987).
V. Hagen, A. Hagen, S. Heer, R. Mitzner, and H. Niedrich,Pharmazie,44, 20 (1989).
M. A. Hassan, E. A. Soliman, and A. A. Hamed,Rev. Roum. Chim.,27, 963 (1982);Chem. Abstr.,98, 89133 (1983).
A. R. Katritzky, S. Rachwal, T. P. Smith, and P. J. Steel,J. Heterocycl. Chem.,32, 179 (1995).
P. Bamfield, E. D. Harvey, and N. Hughes, G. Brit. Pat. 2144740;Chem. Abstr.,104, 34009 (1986).
I. Yokomichi, T. Haga, K. Nagatani, and T. Nakajima, U.S. Pat. 4349681;Chem. Abstr.,97, 216025 (1982).
T. Haga, K. Fujikawa, T. Koyanagi, T. Nakajima, and K. Hayashi,Heterocycles,22, 117 (1984).
T. R. Perrior, A. J. Whittle, and D. J. Tapolczay, Eur. Pat. 357201;Chem. Abstr.,113, 172036 (1990).
N. Matsuo, H. Takeda, T. Yano, S. Nishida, and K. Tsushima, Jpn. Pat. 6172754;Chem. Abstr.,105, 97337 (1986).
K. Matsumoto, T. Uryu, and M. Munakata,Chem. Express,3, 739 (1988).
E. Hang and D. C. Baker,Synthesis, No. 12, 905 (1989).
M. Mamaghani and R. E. Banks,J. Sci. Islamic Repub. Iran,5, 98 (1994);Chem. Abstr.,123, 285715 (1995).
W. S. Saari, U.S. Pat. 4456604;Chem. Abstr.,101, 130718 (1984).
W. S. Saari, U.S. Pat. 4442103;Chem. Abstr.,101, 60140 (1984).
N. Kaishi, K. Araki, and S. Shiraishi,Bull. Chem. Soc. Jpn.,57, 2121 (1984).
L. M. Litvinenko, G. D. Titskii, and E. S. Mitchenko,Zh. Org. Khim.,19, 1970 (1983).
L. M. Litvinenko, G. D. Titskii, and E. S. Mitchenko,Zh. Org. Khim.,20, 1704 (1984).
G. D. Titskii and E. S. Mitchenko,Zh. Org. Khim.,24, 2161 (1988).
M. Sammes, K. W. Ho, M. Tam, and A. R. Katritzky,J. Chem. Soc., Perkin Trans 1, No. 5, 973 (1983).
D. A. De Bie, B. Geurtsen, and H. C. van der Plas,J. Org. Chem.,50, 484 (1985).
D. A. De Bie, B. Geurtsen, I. E. Berg, and H. C. van der Plas,J. Org. Chem.,51, 3209 (1986).
J. W. Streef, H. J. den Hertog, and H. C. van der Plas,J. Heterocycl. Chem.,22, 985 (1985).
R. J. Ife, Eur. Pat. 113572;Chem. Abstr.,102, 6529 (1985).
Toyo Soda Mfg. Co., Ltd., Jpn. Pat. 60112768;Chem. Abstr.,103, 215186 (1985).
Toyo Soda Mfg. Co., Ltd., Jpn. Pat. 60112769;Chem. Abstr.,103, 215187 (1985).
D. Nisato and P. Carminati, Fr. Pat. 2467849;Chem. Abstr.,96, 35101 (1982).
A. Gilbert and S. Krestonosich,J. Chem. Soc., Perkin Trans. 1, No. 11, 2531 (1980).
Toyo Soda Mfg. Co., Ltd., Jpn. Pat. 60113762;Chem. Abstr.,102, 220761 (1985).
G. Scheffler, J. Engel, V. Jakovlev, B. Nickel, and K. Thiemer, Eur. Pat. 149088;Chem. Abstr.,103, 215189 (1985).
Toyo Soda Mfg. Co., Ltd., Jpn. Pat. 60112767;Chem. Abstr.,103, 196012 (1985).
Toyo Soda Mfg. Co., Ltd., Jpn. Pat. 60137631;Chem. Abstr.,102, 220760 (1985).
K. Tsuzuki, T. Uotani, and M. Hashihama, Jpn. Pat. 60169463;Chem. Abstr.,104, 50798] (1986).
Toyo Soda Mfg. Co., Ltd., Jpn. Pat. 59122468;Chem. Abstr.,102, 6214 (1985).
P. E. Cross and R. P. Dickinson, Eur. Pat. 291210;Chem. Abstr.,110, 154160 (1989).
K. Samula and B. Rostafinska,Pol. Chem. J.,55, 1667 (1981).
A. Greiner,Synthesis, No. 4, 312 (1989).
S. Cacchi, A. Carangio, G. Fabrizi, L. Moro, and P. Pace,Synlett, No. 12, 1400 (1997).
H. Haeuser and G. Walter, Ger. Offen. Pat. 3241429;Chem. Abstr.,101, 72621 (1984).
J. M. Greene, A. J. Pike, E. R. Lavagnino, and E. C. Taylor, Eur. Pat. 149537;Chem. Abstr.,103, 215190 (1985).
R. Bernardi, T. Caronna, S. Morrocchi, M. Ursini, and B. M. Vittimberga,J. Chem. Soc., Perkin Trans. 1, No. 1, 97 (1990).
A. S. Kiselyov and L. Strekowski,Synth. Commun.,24, 2387 (1994).
K. Yamauchi, K. Nakao, F. Nishimura, and K. Tamaoki, Jpn. Pat. 0138072;Chem. Abstr.,111, 57552 (1989).
B. Narasaiah, A. Sivaprasad, and R. V. Venkataratnan,J. Fluorine Chem.,67, 87 (1994).
D. Quarroz, Eur. Pat. 90173;Chem. Abstr.,100, 68178 (1984).
Yu. V. Kurbatov and M. A. Solekhova,Zh. Org. Khim.,19, 663 (1983).
Yu. V. Kurbatov and M. A. Solekhova,Khim. Geterotsikl. Soedin., No. 7, 936 (1986).
E. B. Lifshits, Yu. M. Karpova, and M. N. Ushomirskii,Khim. Geterotsikl. Soedin., No. 9, 1278 (1989).
T. Hisano, T. Matsuoka, M. Ichikawa, and M. Hamana,Heterocycles,14, 19 (1980).
R. A. Abramovitch, J. Pilski, A. Konitz, and P. Tomasik,J. Org. Chem.,48, 4391 (1983).
W. Czuba and J. Wodzinska,Pol. J. Chem.,68, 1343 (1994).
Y. Tamura, M. Fujita, C. L. Ching, H. Kiyokawa, K. Ueno, and Y. Kita,Heterocycles,15, 871 (1981).
J. B. Campbell, E. R. Lavagnino, and A. J. Pike, Eur. Pat. 159112;Chem. Abstr.,104, 148751 (1986).
N. Ple and G. Queguiner,J. Heterocycl. Chem.,26, 475 (1989).
B. R. Eric, W. J. Jondi, and A. E. Tipping,J. Fluorine Chem.,77, 87 (1996).
V. G. Kartsev, E. M. Gizatullina, and Z. G. Aliev,Khim. Geterotsikl. Soedin., No. 3, 369 (1992).
Ishihara Sangyo Kaisha Ltd., Jpn. Pat. 58213776;Chem. Abstr.,100, 209853 (1984).
L. R. Hatton, E. W. Parnell, and D. A. Roberts, Ger. Offen. Pat. 3408727;Chem. Abstr.,102, 45922 (1985).
Ishihara Sangyo Kaisha Ltd., Jpn. Pat. 58198469;Chem. Abstr.,100, 156508 (1984).
A. M. Sipygin and Z. G. Aliev,Khim. Geterotsikl. Soedin., No. 11, 1495 (1993).
T. Talik, J. Lorenc, and M. Pupin,Pr. Nauk Akad. Ekon. im. Oskara Langego Wroclawiu,255, 131 (1984).
L. Davis, G. E. Olsen, J. T. Klein, K. J. Kapples, F. P. Huger, C. P. Smith, W. W. Petko, M. Confoldt, and R. C. Effland,J. Med. Chem.,39, 582 (1996).
J. B. Campbell, J. M. Greene, E. R. Lavagnino, D. N. Gardner, A. J. Pike, J. Snoddy, and E. C. Taylor,J. Heterocycl. Chem.,23, 669 (1986).
N. R. Ayyangar, S. Madan Kumar, and K. V. Srinivasan,Synthesis, No. 7, 616 (1987).
H. A. Al-Lohedan,Tetrahedron,46, 3593 (1990).
R. B. Rogers, B. C. Gerwick, and E. A. Egli, U.S. Pat. 4474599;Chem. Abstr.,102, 45956 (1985).
A. A. Tolmachev and E. S. Kozlov,Khim. Geterotsikl. Soedin., No. 12, 1587 (1986).
Wenhao Hu, C. C. Pai, C. C. Chen, Guopin Xue, and A. S. C. Chan,Tetrahedron: Asymmetry,9, 3241 (1998).
Ya. A. Dofman and L. V. Levina,Khim. Geterotsikl. Soedin, No. 1, 128 (1992).
E. Anders and F. Markus,Tetrahedron Lett.,28, 2675 (1987).
E. Anders and F. Markus,Chem. Ber.,120, 2675 (1987).
D. Fukuoka, K. Takahashi, and I. Hashimoto, Ch. Pat. 88100659;Chem Abstr.,110, 173099 (1989).
Ishihara Sangyo Kaisha Ltd., Jpn. Pat. 81123970;Chem. Abstr.,96, 6602 (1982).
V. M. Petrichenko and M. E. Konshin, in:Synthetic Methods of Basic Hetero-Organic Compounds [in Russian], I. I. Lapkin (ed.), Perm State Univ., Perm (1982), p. 69.
R. Nishiyama, K. Fujikawa, T. Haga, T. Toki, T. Komoyoji, N. Sakashita, and K. Maeda, Can. Pat. 1176637;Chem. Abstr., 102, 149119 (1985).
M. Boger and J. Ehrenfreund, Eur. Pat. 40179;Chem. Abstr.,96, 85429 (1982).
H. Rempfler, R. Schurter, and W. Foery, U.S. Pat. 4325729;Chem. Abstr.,97, 23638 (1982).
Ishihara Sangyo Kaisha Ltd., Jpn. Pat. 57145861;Chem. Abstr.,98, 71950 (1983).
T. P. Selby, Eur. Pat. 61913;Chem. Abstr.,98, 71949 (1983).
Ishihara Sangyo Kaisha Ltd., Jpn. Pat. 82102865;Chem. Abstr.,97, 182218 (1982).
H. Rempfler and B. Bohner, Eur. Pat. 50097;Chem. Abstr.,97, 144777 (1982).
Ishihara Sangyo Kaisha Ltd., Jpn. Pat. 8277674;Chem. Abstr.,97, 127508 (1982).
Ishihara Sangyo Kaisha Ltd., Jpn. Pat. 57109768;Chem. Abstr.,98, 89175 (1983).
R. C. Krauss, Eur. Pat. 66827;Chem. Abstr.,98, 198027 (1983).
R. C. Krauss, U.S. Pat. 4410701;Chem. Abstr.,100, 34417 (1984).
R. Kirsten, R. Andree, U. Busse, A. Marhold, H. J. Santel, R. R. Schmidt, K. Luerssen, and H. Strang, Ger. Offen. Pat. 3729071;Chem. Abstr.,109, 149365 (1988).
T. J. Adaway, Eur. Pat. 128658;Chem. Abstr.,102, 166617 (1985).
P. A. Cain, U.S. Pat. 4521425;Chem. Abstr.,103, 160402 (1985).
Ishihara Sangyo Kaisha Ltd., Jpn. Pat. 60112765;Chem. Abstr.,104, 5792 (1986).
T. Oe, Y. Ono, K. Kawasaki, and T. Nakajima, Eur. Pat. 359547;Chem. Abstr.,113, 115095 (1982).
R. Becker, W. Hoffmann, H. G. Oeser, W. Rohr, and J. Varwig, Ger. Offen. Pat. 3151589;Chem. Abstr.,100, 103180 (1984).
R. Schurter, U. Siegrist, H. Rempfler, and P. Baumeister, Eur. Pat. 178260;Chem. Abstr.,105, 97327 (1986).
R. L. Burson, Eur. Pat. 136593;Chem. Abstr.,103, 104856 (1985).
H. Johnston, U.S. Pat. 4360524;Chem. Abstr.,98, 125892 (1983).
L. D. Markley, Y. C. Tong, J. K. Dulworth, D. L. Steward, C. T. Goralski, H. Johnston, S. G. Wood, A. P. Vinogradoff, and T. M. Bargar,J. Med. Chem.,29, 427 (1986).
S. L. Pendalwar, D. T. Chaudhari, and M. R. Patel,Bull. Haffkine Inst.,8, 33 (1980);Chem. Abstr.,97, 55722 (1982).
J. J. Baldwin and G. S. Ponticello, U.S. Pat. 4329351;Chem. Abstr.,97, 72256 (1982).
J. Macor and M. Newman,Heterocycles,31, 805 (1990).
L. Schroeder, R. Mengel, W. Stransky, G. Linden, and S. Lust, Ger. Offen. Pat. 3242519;Chem. Abstr.,101, 90778 (1984).
K. J. Hwang and S. K. Park,Synth. Commun.,20, 949 (1990).
T. Kagawa, T. Uotani, and K. Tsuzuki, Jpn. Pat. 01153677;Chem. Abstr.,111, 173997 (1989).
Seitetsu Kagaku Co., Ltd., Jpn. Pat. 58154561;Chem. Abstr.,100, 120891 (1984).
P. Ballesteros, R. M. Claramunt, and J. Elguero,Tetrahedron,43, 2557 (1987).
M. I. Attalla, G. R. Burnett, and L. A. Summers,J. Heterocycl. Chem.,22, 319 (1985).
R. S. Dainter, H. Suschitzky, B. J. Wakefield, M. Hughes, and J. Nelson,Tetrahedron Lett.,25, 5693 (1984).
S. K. Kotovskaya, G. A. Mokrushina, and I. Ya. Postovskii,Khim. Geterotsikl. Soedin., No. 3, 373 (1983).
K. Rajyalakshmi and V. R. Srinivasan,Indian J. Chem., Sect. B,18, 226 (1979).
R. S. Dainer, L. Julia, H. Suschitzky, and B. J. Wakefield,J. Chem. Soc., Perkin Trans. 1, No. 12, 2897 (1982).
R. E. Banks, W. Jondi, and A. E. Tipping,J. Chem. Soc., Chem. Commun., No. 17, 1268 (1989).
A. Nahara and Y. Maki, Eur. Pat. 174726;Chem. Abstr., 105, 133883 (1986).
L. Eggers and W. Grahn,Synthesis, No. 6, 763 (1996).
T. Talik and Z. Talik,Pr. Nauk. Akad. Ekon. im. Oskara Langego Wroclawiu,278, 163 (1984);Chem. Abstr.,103, 104818 (1985).
T. Fujii, T. Hiraga, and M. Ohba,Chem. Pharm. Bull.,29, 2503 (1981).
A. R. Katritzky, R. C. Patel, and M. Shanta,J. Chem. Soc., Perkin Trans. 1, No. 9, 1888 (1980).
P. Tomasik, A. Woszczyk, R. A. Abramovitch,J. Heterocycl. Chem.,16, 1283 (1979).
T. Umemoto and G. Tomizawa,Tetrahedron Lett.,28, 2705 (1987).
S. Rosen, D. Hebel, and D. Zamiz,J. Am. Chem. Soc.,109, 3789 (1987).
S. Rosen and D. Hebel,Heterocycles,28, 249 (1989).
D. Hebel and S. Rosen,J. Org. Chem.,53, 1123 (1988).
M. Ueki, M. Honda, Y. Kazama, and T. Katoh,Synthesis, No. 1, 21 (1994).
C. O. Okafor,J. Org. Chem.,47, 592 (1982).
Z. Weglinski,Pr. Nauk. Akad. Ekon. im. Oskara Langego Wroclawiu,435, 149 (1988);Chem. Abstr.,112, 76911 (1990).
J. Becher and J. Lundsgaard,Phosphorus Sulfur Relat. Elem.,14, 131 (1983).
J. Becher and J. Lundsgaard,Sulfur Lett.,1, 5 (1982).
J. M. Teulon, Eur. Pat. 162776;Chem. Abstr.,104, 109668 (1986).
V. N. Knyazev, V. N. Drozd, and T. Ya. Mozhaeva,Izv. Timiryazevsk. S-kh. Akad., No. 1, 182 (1983).
R. G. Suhr and J. L. Miesel, U.S. Pat. 4264605;Chem. Abstr.,96, 52182 (1982).
C. T. Redemann, U.S. Pat. 4490380;Chem. Abstr.,102, 166625 (1985).
M. Ueki and T. Watanabe, Jpn. Pat. 06228098;Chem. Abstr.,121, 300773 (1994).
W. W. Brand and J. M. Gullo, Eur. Pat. 36638;Chem. Abstr.,96, 142709 (1982).
K. C. Pugh, L. Gera, and J. M. Stewart,Peptide Chemistry 1992, Proc. Jpn. Symp. 2nd 1992, (1993), p. 37;Chem. Abstr.,121, 9114 (1994).
K. A. Memoli,Tetrahedron Lett.,37, 3617 (1996).
S. V. Amosova, V. I. Gostevskaya, G. M. Gavrilova, and A. V. Afonin,Zh. Org. Khim.,29, 1501 (1993).
Yu. C. Tong, U.S. Pat. 4558134;Chem. Abstr.,105, 6409 (1986).
S. Kondo, M. Nakanishi, and K. Tsuba,J. Heterocycl. Chem.,21, 1243 (1984).
R. Beugelmans, M. Bois-Choussy, and B. Boudet,Tetrahedron,39, 4153 (1983).
L. Testaferri, M. Tiecco, M. Tingoli, D. Chianelli, and M. Montanucci,Synthesis, No. 9, 751 (1983).
B. Boduszek and J. S. Wieczorek,Monatsh. Chem.,111, 1111 (1980).
A. M. Sipyagin, S. V. Pal'tsun, I. A. Pomytkin, and N. N. Aleinikov,Khim. Geterotsikl. Soedin., No. 1, 63 (1994).
N. K. Goswami,Indian J. Chem., Sect. B,21, 364 (1983).
S. G. Woods, B. T. Matyas, A. P. Vinogradoff, and Y. C. Tong,J. Heterocycl. Chem.,21, 97 (1984).
L. Testaferri, M. Tiecco, M. Tigoli, D. Bartoli, and A. Massoli,Tetrahedron,41, 1373 (1985).
N. Furukawa, S. Ogawa, T. Kawai, and S. Oae,Tetrahedron Lett.,24, 3243 (1983).
N. Furukawa, S. Ogawa, T. Kawai, and S. Oae,J. Chem. Soc., Perkin Trans. 1, No. 8, 1839 (1984).
C. Bieniarz and M. J. Cornwell,Tetrahedron Lett.,34, 939 (1993).
Ishihara Sangyo Kaisha Ltd., Jpn. Pat. 58170759;Chem. Abstr.,100, 209626 (1984).
A. M. Sipyagin and Z. G. Aliev,Khim. Geterotsikl. Soedin., No. 9, 1207 (1993).
A. Couture, P. Grandclaudon, and E. Huguerre,J. Heterocycl. Chem.,24, 1765 (1987).
J. B. Adams, Jr., U.S. Pat. 4456469;Chem. Abstr.,101, 191972 (1984).
M. Tiecco, L. Testaferri, M. Tingoli, D. Chianelli, D. Bartoli, and R. Balducci,Tetrahedron,44, 4883 (1988).
L. Syper and J. Mtochowski,Tetrahedron 44, 6119 (1988).
K. Smith, I. Mattheurs, and G. E. Martin,J. Chem. Soc., Perkin Trans. 1, No. 12, 2839 (1987).
J. Chen and G. T. Crisp,Synth. Commun.,22, 683 (1992).
H. J. Cristau, B. Chaband, R. Labandiniere, and H. Christol,Organometallics,4, 657 (1985).
Z. C. Chang, Q. Jiang, B. X. Xu, S. Z. Tu, Z. Y. Ma, P. Zhu, and Q. H. Yang,Yaoxue Xuebao,30, 263 (1995);Chem. Abstr.,123, 55666 (1995).
H. Ban-Oganowska,Chem. Pap.,49, 94 (1995);Chem. Abstr.,124, 55759 (1996).
A. M. Sipyagin, V. V. Kolchanov, and S. V. Pal'tsun,Khim. Geterotsikl. Soedin., No. 9, 1216 (1993).
A. M. Sipyagin, V. V. Kolchanov, and N. N. Sveshnikov,Tetrahedron Lett.,35, 3147 (1994).
L. Bauer and S. Prachayasittikul,Heterocycles,24, 161 (1986).
N. Sato and E. Nagano,J. Heterocycl. Chem.,30, 691 (1993).
Yoshitomi Pharmaceutical Industries, Ltd., Jpn. Pat. 5888362;Chem. Abstr.,99, 122318 (1983).
Yoshitomi Pharmaceutical Industries, Ltd., Jpn. Pat. 58152867;Chem. Abstr.,100, 103181 (1984).
Yoshitomi Pharmaceutical Industries, Ltd., Jpn. Pat. 59112968;Chem Abstr.,101, 210996 (1984).
J. Verbeek, A. V. E. George, R. L. P. De Jong, and L. Brandsma,J. Chem. Soc., Chem. Commun., No. 4, 257 (1984).
J. Verbeek and L. Brandsma,J. Org. Chem.,49, 3857 (1984).
P. Jacob, III, and A. T. Shulgin,Synth. Commun.,11, 957 (1981).
L. Engman and M. P. Cava,Organometallics,1, 470 (1982).
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Dedicated to Professor Henk van der Plas on his 70th birthday.
For No. 2, see [1].
M. V. Lomonosov Moscow State University, Moscow 119899
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 437–494, April, 1999.
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Yurovskaya, M.A., Mit'kin, O.D. Functionalization of pyridines. 3. Reactions forming a carbon-heteroatom bond with group IV, V, and VI elements. Chem Heterocycl Compd 35, 383–435 (1999). https://doi.org/10.1007/BF02319329
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DOI: https://doi.org/10.1007/BF02319329