Summary
Data on the deuteration, alkylation and acylation reactions of potentially tautomeric methyl and methylidene derivatives of pyridine, pyrimidine and pyrazine in media of varying acidity and basicity have been collated. Whether these reactions occur via the aromatic tautomers, the more reactive methylidene tautomers or predominantly by generation of mesomeric anions from both tautomers is examined.
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References
J. Elguero, C. Marzin, A. R. Katritzky and P. Linda, The Tautomerism of Heterocycles, Academic Press, New York (1976), p.179.
V. V. Lapachev, O. P. Petrenko and V. P. Mamaev, Usp. Khim.,59, 457 (1990).
A. R. Katritzky and C. W. Rees (eds.), Comprehensive Heterocyclic Chemistry, Pergamon, Oxford (1984), Vol. 2, Part 2A, pp. 1–365; Vol. 3, Part 2B, pp. 1–199.
D. J. Brown, The Pyrimidines in: The Chemistry of Heterocyclic Compounds, A. Weissberger and E. C. Taylor (eds.), Vol. 52, Interscience, New York (1994), p. 264.
A. R. Katritzky and R. Taylor, Electrophilic Substitution in Heterocycles, Adv. Heterocycl. Chem.,47, 276 (1990).
A. F. Pozharskii, Theoretical Basis of Heterocyclic Chemistry [in Russian], Khimiya, Moscow (1985), p. 186.
P. Molina, P. M. Fresneda and M. C. Lajara, J. Heterocycl. Chem.,22, 113 (1985).
M. Drobnic-Kosorok, K. Jernejc-Pfundner, J. Peternel, B. Stanovnic and M. Tisler, J. Heterocycl. Chem.,13, 1279 (1976).
J. Ezquerra and J. Alvarez-Builla, J. Heterocycl. Chem.,23, 1151 (1986).
Z. Huang and H. Wamhoff, Chem. Ber.,117, 1856 (1984).
M. J. Cook, A. R. Katritzky, P. Linda and R. D. Tack, J. Chem. Soc. Perkin2, No. 10, 1295 (1972).
Yu. B. Vysotskii, B. P. Zemskii, T. V. Stupkinov, R. S. Sagitullin, A. N. Kost and P. P. Shvaika, Khim. Geterotsikl. Soedin., No. 11, 1496 (1979).
P. W. Hickmott, Tetrahedron,40, 2989 (1984).
D. T. Hurst, Austral. J. Chem.,36, 1659 (1983).
T. V. Stupnikova, B. P. Zemskii, R. S. Sagitullin and A. N. Kost, Khim. Geterotsikl. Soedin., No. 3, 291 (1982).
V. I. Minkin, L. P. Olekhnovich and Yu. A. Zhdanov, Molecular Diazine Tautomeric Systems [in Russian], Rostov Univ. Press, Rostov on Don (1977), p. 48.
P. Molina and A. Lorenzo, Tetrahedron. Lett.,24, 5805 (1983).
A. R. Katritzky and R. Awartani, Tetrahedron,38, 2505 (1982).
O. R. Rodig, Pyridine and Its Derivatives: The Chemistry of Heterocyclic Compounds, R. A. Abramovitch (ed.), Vol. 14, Supplement, Part 1, Interscience, New York (1974), p. 351.
L. I. Belen'kii, Khim. Geterotsikl. Soedin., No. 6, 749 (1986).
M. I. Terekhova, E. S. Petrov, O. P. Shkurko, M. A. Mikhaleva, V. P. Mamaev and A. I. Shatenshtein, Zh. Org. I: Khim.,19, 465 (1983).
R. R. Fraser, T. S. Mansour and S. Savard, J. Org. Chem.,50, 3232 (1985).
N. N. Zatsepina and I. F. Tupitsyn, Khim. Geterotsikl. Soedin., No. 12, 1587 (1974).
A. R. Katritzky, N. Z. Kucharska and J. D. Rowe, J. Chem. Soc., No. 5, 3093 (1965).
A. R. E. Carey, S. Eustace, R. A. M. O'Ferrall and B. A. Murray, J. Chem. Soc. Perkin2, No. 11, 2285 (1993).
V. V. Lapachev, O. A. Zagulyaeva and V. P. Mamaev, Dokl. Akad. Nauk SSSR.,236, 113 (1977).
F. W. Krock and F. Krohne, Chem. Ber,102, 669 (1969).
S.-O. Chua, M. J. Cook and A. R. Katritzky, J. Chem. Soc., Perkin 2, No. 15, 2111 (1973).
J. A. Berson, E. M. Evleth and Z. Hamlet, J. Am, Chem. Soc.,87, 2887 (1965).
G. V. Boyd and A. D. Ezekiel, J. Chem. Soc. Part C, No. 19, 1866 (1967).
S. Golding, A. R. Katritzky and H. Z. Kucharska, J. Chem. Soc., No. 5, 3090 (1965).
S. Restle and C. G. Wermuth, Tetrahedr. Lett., No. 50, 4837 (1979).
O. A. Zagulyaeva, O. A. Grigorkina, V. I. Mamatyuk and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 3, 397 (1982).
I. V. Oleinik, O. Ya. Zagulyaeva, A. Yu. Denisov and V. A. Mamaev, Khim. Geterotsikl. Soedin., No. 7, 960 (1990).
V. V. Lapachev, O. A. Zagulyaeva, O. P. Petrenko, S. F. Bychkov and V. A. Mamaev, Khim. Geterotsikl. Soedin., No. 6, 827 (1984).
A. R. Katritzky, Handbook of Heterocyclic Chemistry, Pergamon, Oxford (1985), p. 161.
Y. Nakashima, M. Fukunaga, K. Suzuki and K. Takhashi, Bull. Chem. Soc. Jpn.,66, 2143 (1993).
A. I. Shatenshtein and E. N. Zvyagintseva, Dokl. Akad. Nauk SSSR,117, 852 (1957).
T. I. Abramovich, I. P. Gragerov and V. V. Perekalin, Dokl. Akad. Nauk SSSR,121, 295 (1958).
Y. Kawazoe, M. Ohnishi and Y. Yashioka, Chem. Pharm. Bull.,15, 1225 (1967).
H. Yamanaka, H. Abe, T. Sakamoto, M. Hiranuma and A. Kamata, Chem. Pharm. Bull.,25, 1821 (1977).
Y. Kawazoe, Y. Yoshioka, M. Yamada and H. Igeta, Chem. Pharm. Bull.,15, 2000 (1967).
A. Ohsawa, T. Uezu and H. Igeta, Chem. Pharm. Bull.,26, 2428 (1978).
T. J. Batterham, D. J. Brown and M. N. Paddon-Row, J. Chem. Soc., Part B, No. 3, 171 (1967).
O. P. Petrenko, V. G. Storozhenko, V. V. Lapachev, V. I. Mamatyuk and V. P. Mamaev, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1032 (1983).
J. A. Zoltewicz and L. W. Deady, Heterocycl. Chem., A. R. Katritzky (ed.), 22, 79 (1978).
W. Sliwa, G. Matusiak and A. Postawka, Heterocycles,23, 1513 (1985).
W. Sliwa, Heterocycles,24, 181 (1986).
W. Sliwa, Heterocycles29, 557 (1989).
W. Sliwa, L. Chrzastek and M. Mielniczak, Heterocycles,36, 1645 (1993).
W. Sliwa, Khim. Geterotsikl. Soedin., No. 2, 147 (1994)
W S. Bale, A. B. Simmonds and W. F. Trager, J. Chem. Soc. Part B, No. 9, 867 (1966).
M. V. Deichmeister and A. M. Platoshkin, Khim. Geterotsikl. Soedin., No. 1, 333 (1967).
E. A. Oostven, H. C. van der Plas and H. Jongejan, Rec. Trav. Chim.,93, 114 (1974).
L. W. Deady and J. A. Zoltewicz, J. Am. Chem. Soc.,93, 5475 (1971).
T. J. Curphey and K. S. Prasad, J. Org. Chem.,37, 2259 (1972).
O. A. Zagulyaeva, 0. A. Grigorkina, V. I. Mamatyuk and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 11, 1537 (1984).
O. A. Zagulyaeva and V. P. Mamaev, Izv. Sib. Otdel. Akad. Nauk SSSR, Ser. Khim., No. 12, Pt. 5, 55 (1967).
H. C. Brown and W. A. Murphey, J. Am. Chem. Soc.,73, 3308 (1951).
H. C. Brown and B. Karner, U. S. Pat. 2,780,626; Chem. Abs.,51, 9710 (1957).
V. I. Cohen, B. Jin and R. C. Reba, Ann., No. 7, 809 (1993).
L. S. Hart, C. R. J. Killen and K. D. Saunders, J. Chem. Soc. Chem. Communs., No. 1, 24 (1979).
A. Katoh, Y. Omote and C. Kashima, J. Heterocycl. Chem.,21, 915 (1984).
J. D. Behan and R. Levine, J. Org. Chem.,26, 3379 (1961).
G. P. Rizzi, J. Org. Chem.,33, 1333 (1968).
T. Yamazaki, K. Matoba and S. Imoto, Heterocycles,4, 713 (1976).
R. C. Paul, D. Singh W S. S. Sandhu, J. Chem. Soc., No. 1, 315 (1959).
A. K. Sheinkman, S. I. Suminov and A. N. Kost, Usp. Khim.,42, 1415 (1973).
A. N. Kost and A. K. Sheinkman, Zh. Obshch. Khim.,33, 2077 (1963).
Yu. V. Kurbatov, A. S. Kurbatova, M. A. Solekhova, O. S. Otroshchenko and A. S. Sadykov, Nauch. Trudy Samarkand. Univ., Pt. 167, 192 (1969); Ref. Zh. Khim., 2Zh331 (1970).
C. D. Gutsche and H. W. Voges, J. Org. Chem.,32, 2685 (1967).
F. S. Babichev and Yu. M. Volovenko, Khim. Geterotsikl. Soedin., No. 7, 1005 (1975).
T. Suzuki and K. Mitsuhashi, J. Heterocycl. Chem.,22, 1487 (1985).
V. M. Cherkasov, L. P. Prikazchikova, B. M. Khutova, 1. F. Vladimirtsev and 1. V. Boldyrev, Khim. Geterotsikl. Soedin., No. 8, 1132 (1973)
L. P. Prikazchikova, B. M. Khutova and V. M. Cherkasov, Khim. Geterotsikl. Soedin., No. 8, 1146 (1974).
L. P. Prikazchikova, B. M. Khutova and E. A. Romanenko, Khim. Geterotsikl. Soedin., No. 9, 1256 (1978).
B. M. Kutova, S. V. Klyuchko, L. 1. Prikazchikova and V. M. Cherkasov, Khim. Geterotsikl. Soedin., No. 5, 687 (1982).
B. M. Khutova, L. I. Prikazchikova and V. M. Cherkasov, Khim. Geterotsikl. Soedin., No. 4, 531 (1983).
N. N. Goldberg, L. B. Barkley and R. Levine, J. Am. Chem. Soc.,73, 4301 (1951).
S. Raynolds and R. Levine, J. Am. Chem. Soc.,82, 472 (1960).
H. Yamanaka, H. Abe and T. Sakamoto, Chem. Pharm. Bull.,25, 3334 (1977).
A. Ohsawa, T. Uezu and H. Igeta, Chem. Pharm. Bull.,26, 3633 (1978).
B. R. Baker and F. J. McEvoy, J. Org. Chem.,20, 118 (1955).
P. W. Hickmott, Chem. Ind., No. 18, 731 (1974).
A. N. Vasil'ev and L. K. Mushkalo, Zh. Obshch. Khim.,62, 2087 (1992).
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Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk 630090. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 816–829, June, 1995. Original article submitted May 16, 1995.
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Zagulyaeva, O.A., Oleinik, I.V. Hydrogen exchange, alkylation and acylation of potentially tautomeric methyl and methylidene derivatives of pyridine and diazines (Review). Chem Heterocycl Compd 31, 715–725 (1995). https://doi.org/10.1007/BF01169069
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DOI: https://doi.org/10.1007/BF01169069