Nitrenium ions and problem of direct electrophilic amination of aromatic compounds

Russian Journal of Organic Chemistry

Volumn 41, Issue 4, 2005, Pages 473-504

  Borodkin, G I ^a,b   Shubin, V G ^a  

^a N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b NOVOSIBIRSK STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AROMATIC COMPOUND; AZIDE; ESTER; HYDRAZINE; ION; POLYCYCLIC AROMATIC HYDROCARBON; PYRIDINIUM DERIVATIVE; REAGENT; SULFONIUM DERIVATIVE;

AB INITIO CALCULATION; AMINATION; ATOM; CHEMICAL STRUCTURE; CYCLIZATION; ELECTRON; QUANTUM CHEMISTRY; RADIOCHEMISTRY; REACTION ANALYSIS; REVIEW; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 21544432729     PISSN: 10704280     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11178-005-0193-z     Document Type: Review

References (184)

1. Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Moscow: Novaya Volna, 2002, vols. 1, 2.
2. Soldatenkov, A.T., Kolyadina, N.M., and Shendrik, I.V., Osnovy organicheskoi khimii lekarstvennykh veshchestv (Principles of the Organic Chemistry of Drugs), Moscow: Mir, 2003, p. 8.
3. Lednicer, D., Strategies for Organic Drug Synthesis and Design, New York: Wiley, 1998, p. 1.
4. Belan, S.R., Grapov, A.F., and Mel'nikova, G.M., Novye pestitsidy. Spravochnik (New Pesticides. Handbook), Moscow: VNIIKhSZR, 2001, p. 1.
5. Gaile, A.A., Somov, V.E., and Varshavskii, O.M., Aromaticheskie uglevodorody: vydelenie, primenenie, rynok (Aromatic Hydrocarbons: Isolation, Application, and Market), St. Petersburg: Khimizdat, 2000.
6. Krasovitskii, B.M. and Afanasiadi, L.M., Mono- i bifluorofory (Mono- and Bifluorophores), Khar'kov: Inst. Monocryst., 2002.
7. Lehn, J.-M., Supramolecular Chemistry: Concepts and Perspectives, Weinheim: VCH, 1995.
8. Translated under the title Supramolekulyarnaya khimiya, Novosibirsk: Nauka, Sib. Predpr. Ross. Akad. Nauk, 1998, pp. 111, 167.
9. Benigni, R., Giuliani, A., Franke, R., and Gruska, A., Chem. Rev., 2000, vol. 100, p. 3697.
10. McClelland, R.A., Ahmad, A., Dicks, A.P., and Licence, V.E., J. Am. Chem. Soc., 1999, vol. 121, p. 3303.
11. McClelland, R.A., Gadosy, T.A., and Ren, D., Can. J. Chem., 1998, vol. 76, p. 1327.
12. Novak, M. and Kennedy, S.A., J. Phys. Org. Chem., 1998, vol. 11, p. 71.
13. Hoffman, G.R. and Fuchs, R.P.P., Chem. Res. Toxicol., 1997, vol. 10, p. 347.
14. McClelland, R.A., Kahley, M.J., and Davidse, P.A., J. Phys. Org. Chem., 1996, vol. 9, p. 355.
15. McClelland, R.A., Tetrahedron, 1996, vol. 52, p. 6823.
16. Falvey, D.E., J. Phys. Org. Chem., 1999, vol. 12, p. 589.
17. Toteva, M.M and O'Donoghue, A.C., Annu. Rep. Prog. Chem., Sect B: Org. Chem., 2000, vol. 96, p. 291.
18. Comprehensive Organic Chemistry, Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon, 1979, vol. 2.
19. Translated under the title Obshchaya organicheskaya khimiya, Moscow: Khimiya, 1982, vol. 3, p. 168.
20. De Vos, D.E., Dams, M., Sels, B.F., and Jacobs, P.A., Chem. Rev., 2002, vol. 102, p. 3615.
21. Adams, J.P. and Paterson, J.R., J. Chem. Soc., Perkin Trans. 1, 2000, p. 3695.
22. Wolfe, J.P., Wagaw, S., Marcoux, J.-F., and Buchwald, S.L., Acc. Chem. Res., 1998, vol. 31, p. 805;
23. Hartwig, J.F., Angew. Chem., Int. Ed. Engl., 1998, vol. 37, p. 2046;
24. Belfield, A.J., Brown, G.R., and Foubister, A.J., Tetrahedron, 1999, vol. 55, p. 11399.
25. Simonova, T.P., Nefedov, V.D., Toropova, M.A., and Kirillov, N.F., Usp. Khim., 1992, vol. 61, p. 1061.
26. Ford, G.P. and Scribner, J.D., J. Am. Chem. Soc., 1981, vol. 103, p. 4281.
27. Glover, S.A. and Scott, A.P., Tetrahedron, 1989, vol. 45, p. 1763.
28. Ford, G.P. and Herman, P.S., J. Am. Chem. Soc., 1989, vol. 111, p. 3987.
29. Falvey, D.E. and Cramer, C.J., Tetrahedron Lett., 1992, vol. 33, p. 1705.
30. Barclay, V.J., Hamilton, I.P., and Jensen, P., J. Chem. Phys., 1993, vol. 99, p. 9709.
31. Gobbi, A. and Frenking, G., Chem. Commun., 1993, p. 1162.
32. Gobbi, A. and Frenking, G., Bull. Chem. Soc. Jpn., 1993, vol. 66, p. 3153.
33. Cramer, C.J., Dulles, F.J., Storer, J.W., and Worthington, S.E., Chem. Phys. Lett., 1994, vol. 218, p. 387.
34. Wright, T.G. and Miller, T.A., J. Phys. Chem., 1996, vol. 100, p. 4408.
35. Osmann, G., Bunker, P.R., Jensen, P., and Kraemer, W.P., J. Mol. Spectrosc., 1997, vol. 186, p. 319.
36. Milburn, R.K., Rodriquez, C.F., and Hopkinson, A.C., J. Phys. Chem. B, 1997, vol. 101, p. 1837.
37. Van Huis, T.J., Leininger, M.L., Sherrill, C.D., and Schaefer, H.F., Collect. Czech. Chem. Commun., 1998, vol. 63, p. 1107.
38. Gonzalez, C., Restrepo-Cossio, A., Marquez, M., Wiberg, K.B., and De Rosa, M., J. Phys. Chem. A, 1998, vol. 102, p. 2732.
39. Stephens, J.C., Yamaguchi, Y., Sherrill, C.D., and Schaefer, H.F., J. Phys. Chem. A, 1998, vol. 102, p. 3999.
40. Marquez, M., Mari, F., and Gonzalez, C.A., J. Phys. Chem. A, 1999, vol. 103, p. 6191.
41. Stephens, J.C., Yamaguchi, Y., and Schaefer, H.F., J. Mol. Struct. (Theochem), 1999, vols. 461-462, p. 41.
42. Osmann, G., Bunker, P.R., Kraemer, W.P., and Jensen, P., Chem. Phys. Lett., 2000, vol. 318, p. 597.
43. Dixon, D.A., Feller, D., and Peterson, K.A., J. Chem. Phys., 2001, vol. 115, p. 2576.
44. Bronzolino, N. and Gzandinetti, F., J. Mol. Struct. (Theochem), 2003, vol. 635, p. 221.
45. Ford, G.P. and Herman, P.S., J. Mol. Struct. (Theochem), 1990, vol. 204, p. 121.
46. Cramer, C.J. and Worthington, S.E., J. Phys. Chem., 1995, vol. 99, p. 1462.
47. Krogh-Jespersen, K., Tetrahedron Lett., 1980, vol. 21, p. 4553.
48. Smith, D.A. and Bitar, J., J. Org. Chem., 1993, vol. 58, p. 6.
49. Li, Q.S. and Cheng, L.P., J. Phys. Chem. A, 2003, vol. 107, p. 5561.
50. Ding, Y.-H., Li, Z.-S., Huang, X.-R., and Sun, C.-C., J. Phys. Chem. A, 2001, vol. 105, p. 7085.
51. Glover, S.A., Scott, A.P., and Tarrant, G.J., Abstracts of Papers, Electronic Conf. on Heterocyclic Chemistry, June 24-July 22, 1996, p. 1.
52. Ford, G.P. and Herman, P.S., J. Mol. Struct. (Theochem), 1991, vol. 236, p. 269.
53. Cramer, C.J., Dulles, F.J., and Falvey, D.E., J. Am. Chem. Soc., 1994, vol. 116, p. 9787.
54. Shcherbinin, M.B., Erusalimskii, G.B., Bal'tser, A.E., Bazanov, A.G., and Ostrovskii, V.A., Russ. J. Org. Chem., 1995, vol. 31, p. 1622.
55. Cramer, C.J. and Falvey, D.E., Tetrahedron Lett., 1997, vol. 38, p. 1515.
56. Moran, R.J., Cramer, C., and Falvey, D.E., J. Org. Chem., 1997, vol. 62, p. 2742.
57. Sullivan, M.B., Brown, K., Cramer, C.J., and Truhlar, D.G., J. Am. Chem. Soc., 1998, vol. 120, p. 11778.
58. Simonova, T.P., Shurov, S.N., Nefedov, V.D., Toropova, M.A., and Avrorin, V.V., Russ. J. Org. Chem., 1998, vol. 34, p. 74.
59. Ford, G.P., Herman, P.S., and Thompson, J.W., J. Comput. Chem., 1999, vol. 20, p. 231.
60. Novak, M. and Lin, J., J. Org. Chem., 1999, vol. 64, p. 6032.
61. Sullivan, M.B. and Cramer, C.J., J. Am. Chem. Soc., 2000. vol. 122, p. 5588.
62. Pol'shakov, D.A., Tsentalovich, Yu.P., and Gritsan, N.P., Izv. Ross. Akad. Nauk, Ser. Khim., 2000, p. 49.
63. Novak, M. and Rajagopal, S., Adv. Phys. Org. Chem., 2001, vol. 36, p. 167.
64. Zhu, P., Ong, S.Y., Chan, P.Y., Leung, K.H., and Phillips, D.L., J. Am. Chem. Soc., 2001, vol. 123, p. 2645.
65. Zhu, P., Ong, S.Y., Chan, P.Y., Poon, Y.F., Leung, K.H., and Phillips, D.L., Chem. Eur. J., 2001, vol. 7, p. 4928.
66. Parks, J.M., Ford, G.P., and Cramer, C.J., J. Org. Chem., 2001, vol. 66, p. 8997.
67. Chan, P.Y., Ong, S.Y., Zhu, P., Leung, K.H., and Phillips, D.L., J. Org. Chem., 2003, vol. 68, p. 5265.
68. Chan, P.Y., Ong, S.Y., Zhu, P., Zhao, C., and Phillips, D.L., J. Phys. Chem. A, 2003, vol. 107, p. 8067.
69. O'Brien, S.E., Browne, H.L., Bradshaw, T.D., Westwell, A.D., Stevens, M.F.G., and Laughton, C.A., Org. Biomol. Chem., 2003, vol. 1, p. 493.
70. Ford, G.P. and Herman, P.S., J. Chem. Soc., Perkin Trans. 2, 1991, p. 607.
71. Novak, M., Kahley, M.J., Lin, J., Kennedy, S.A., and Swanegan, L.A., J. Am. Chem. Soc., 1994, vol. 116, p. 11626.
72. Cramer, C.J., Truhlar, D.G., and Falvey, D.E., J. Am. Chem. Soc., 1997, vol. 119, p. 12338.
73. Srivastava, S., Ruane, P.H., Toscano, J.P., Sullivan, M.B., Cramer, C.J., Chiapperino, D., Reed, E.C., and Falvey, D.E., J. Am. Chem. Soc., 2000, vol. 122, p. 8271.
74. Grandinetti, F., Hrusak, J., Schroder, D., Karrass, S., and Schwarz, H., J. Am. Chem. Soc., 1992, vol. 114, p. 2806.
75. Cacace, F. and Pepi, F., J. Phys. Chem., 1994, vol. 98, p. 8009.
76. Cacace, F., Grandinetti, F., and Pepi, F., Inorg. Chem., 1995, vol. 34, p. 1325.
77. Hiraoka, K., Nasu, M., Fujimaki, S., and Yamabe, S., J. Phys. Chem., 1995, vol. 99, p. 15822.
78. Ricca, A., Chem. Phys. Lett., 1998, vol. 294, p. 454.
79. Aschi, M., Grandinetti, F., and Vinciguerra, V., Chem. Eur. J., 1998, vol. 4, p. 2366.
80. Aschi, M. and Grandinetti, F., J. Mol. Struct. (Theochem), 2000, vol. 497, p. 205.
81. Grandinetti, F. and Vinciguerra, V., Int. J. Mass. Spectrom., 2002, vol. 216, p. 285.
82. Schoeller, W.W. and Busch, T., Chem. Ber., 1990, vol. 123, p. 971.
83. Nguyen, M.T. and Ha, T.-K., Chem. Phys. Lett., 2000, vol. 317, p. 135.
84. Vij, A., Wilson, W.W., Vij, V., Tham, F.S., Sheehy, J.A., and Christe, K.O., J. Am. Chem. Soc., 2001, vol. 123, p. 6308.
85. Kerkines, I.S.K., Papakondylis, A., and Mavridis, A., J. Phys. Chem. A, 2002, vol. 106, p. 4435.
86. Dixon, D.A., Feller, D., Christe, K.O., Wilson, W.W., Vij, A., Vij, V., Jenkins, H.D.B., Olson, R.M., and Gordon, M.S., J. Am. Chem. Soc., 2004, vol. 126, p. 834.
87. Liu, Y.D., Zhao, J.F., and Li, Q.S., Theor. Chem. Acc., 2002, vol. 107, p. 140.
88. Li, Q.S. and Zhao, J.F., J. Phys. Chem. A, 2002, vol. 106, p. 5928.
89. Li, Q.S., Wang, L.J., and Xu, W.G., Theor. Chem. Acc., 2000, vol. 104, p. 67.
90. Cacace, F., Grandinetti, F., and Pepi, F., Angew. Chem., Int. Ed. Engl., 1994, vol. 33, p. 123.
91. Aschi, M., Cacace, F., Grandinetti, F., and Pepi, F., J. Phys. Chem., 1994, vol. 98, p. 2713.
92. Gibson, S.T., Greene, J.P., and Berkowitz, J., J. Chem. Phys., 1985, vol. 83, p. 4319.
93. Kabbadj, Y., Huet, T.R., Uy, D., and Oka, T., J. Mol. Spectrosc., 1996, vol. 175, p. 277.
94. McIlroy, S., Cramer, C.J., and Falvey, D.E., Org. Lett., 2000, vol. 2, p. 2451.
95. Boche, G., Andrews, P., Harms, K., Marsch, M., Rangappa, K.S., Schimeczek, M., and Willeke, C., J. Am. Chem. Soc., 1996, vol. 118, p. 4925.
96. Boche, G., Rangappa, K., Harms, K., and Marsch, M., Z. Crystallogr., 1996, vol. 211, p. 581.
97. Boche, G., Marsch, M., Willeke, C., and Harms, K., Z. Crystallogr., 1996, vol. 211, p. 583.
98. Wirschun, W. and Jochims, J.C., Synthesis, 1997, p. 233.
99. Sridhar, M.A., Lokanath, N.K., Shashidhara, P.J., Bhadre, G.D.G., and Rangappa, K.S., Z. Crystallogr. New Cryst. Struct., 1997, vol. 212, p. 33.
100. Wirschun, W., Winkler, M., Lutz, K., and Jochims, J.C., J. Chem. Soc., Perkin Trans. 1, 1998, p. 1755.
101. Al-Soud, Y.A., Shrestha-Dawadi, P.B., Winkler, M., Wirschun, W., and Jochims, J.C., J. Chem. Soc., Perkin Trans. 1, 1998, p. 3759.
102. Hoffmann, F. and Griehl, C., J. Mol. Struct., 1998, vol. 440, p. 113.
103. Katritzky, A.R., Zhang, G.-F., Pernak, J., and Fan, W.-Q., Heterocycles, 1993, vol. 36, p. 1253.
104. Robert, M., Neudeck, A., Boche, G., Willeke, C., Rangappa, K.S., and Andrews, P., New J. Chem., 1998, vol. 22, p. 1437.
105. Pause, L., Robert, M., Heinicke, J., and Kuhl, O., J. Chem. Soc., Perkin Trans. 2, 2001, p. 1383.
106. Trifonov, R.E., Alkorta, I., Ostrovskii, V.A., and Elguero, J., Heterocycles, 2000, vol. 52, p. 291.
107. Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, G., and Taylor, R., J. Chem. Soc., Perkin Trans. 2, 1987, p. S1.
108. Current Trends in Organic Synthesis, Scolastico, C. and Nicotra, F., Eds., New York: Plenum, 1998, p. 97.
109. Bock, H. and Kompa, K.-L., Chem. Ber., 1966, vol. 99, p. 1361.
110. Bock, H. and Kompa, K.-L., Chem. Ber., 1966, vol. 99, p. 1357.
111. Kovacic, P., Lange, R.M., Foote, J.L., Goralski, C.T., Hiller, J.J., and Levisky, J.A., J. Am. Chem., Soc., 1964, vol. 86, p. 1650.
112. Kovacic, P., Goralski, C.T., Hiller, J.J., Levisky, J.A., and Lange, R.M., J. Am. Chem. Soc., 1965, vol. 87, p. 1262.
113. Kovacic, P., Lowery, M.K., and Field, K.W., Chem. Rev., 1970, vol. 70, p. 639.
114. Belen'kaya, R.S., Verevkin, S.P., Zimichev, A.V., and Rozhnov, A.M., Zh. Org. Khim., 1993, vol. 29, p. 570.
115. Kikugawa, Y. and Kawase, M., J. Am. Chem. Soc., 1984, vol. 106, p. 5728.
116. Kawase, M., Kitamura, T., and Kikugawa, Y., J. Org. Chem., 1989, vol. 54, p. 3394.
117. Kikugawa, Y. and Shimada, M., Chem. Lett., 1987, p. 1771.
118. Kikugawa, Y., Shimada, M., and Matsumoto, K., Heterocycles, 1994, vol. 37, p. 293.
119. Glover, S.A., Goosen, A., McCleland, C.W., and Schoonraad, J.L., Tetrahedron, 1987, vol. 43, p. 2577.
120. Glover, S.A., Rowbottom, C.A., Scott, A.P., and Schoonraad, J.L., Tetrahedron, 1990, vol. 46, p. 7247.
121. Lee, S.J., Terrazas, M.S., Pippel, D.J., and Beak, P., J. Am. Chem. Soc., 2003, vol. 125, p. 7307.
122. Takeuchi, H., Taniguchi, T., and Ueda, T., J. Chem. Soc., Perkin Trans. 2, 2000, p. 295.
123. Takeuchi, H., Tateiwa, J.-i., Hata, S., Tsutsumi, K., and Osaki, Y., Eur. J. Org. Chem., 2003, p. 3920.
124. Shudo, K., Ohta, T., and Okamoto, T., J. Am. Chem. Soc., 1981, vol. 103, p. 645.
125. Spence, J.D., Raymond, A.E., and Norton, D.E., Tetrahedron Lett., 2003, vol. 44, p. 849.
126. Naicker, K.P, Pitchumani, K., and Varma, R.S., Catal. Lett., 1998, vol. 54, p. 165.
127. Miyazawa, E., Sakamoto, T., and Kikugawa, Y., J. Chem. Soc., Perkin Trans. 2, 1998, p. 7.
128. Novak, M. and Kazerani, S., J. Am. Chem. Soc., 2000, vol. 122, p. 3606.
129. Novak, M. and Rangappa, K.S., J. Org. Chem., 1992, vol. 57, p. 1285.
130. Novak, M., Rangappa, K.S., and Manitsas, R.K., J. Org. Chem., 1993, vol. 58, p. 7813.
131. Meier, C. and Boche, G., Tetrahedron Lett., 1990, vol. 31, p. 1693.
132. Kawase, M. and Kikugawa, Y., Chem. Pharm. Bull., 1981, vol. 29, p. 1615.
133. Kikugawa, Y. and Kawase, M., Chem. Commun., 1991, p. 1354.
134. Wardrop, D.J., Burge, M.S., Zhang, W., and Ortiz, J.A., Tetrahedron Lett., 2003, vol. 44, p. 2587.
135. Wardrop, D.J., Landrie, C.L., and Ortiz, J.A., Synlett, 2003, p. 1352.
136. Miyazawa, E., Sakamoto, T., and Kikugawa, Y., J. Org. Chem., 2003, vol. 68, p. 5429.
137. Miyazawa, E., Sakamoto, T., and Kikugawa, Y., Heterocycles, 2003, vol. 59, p. 149.
138. Kikugawa, Y., Nagashima, A., Sakamoto, T., Miyarawa, E., and Shiiya, M., J. Org. Chem., 2003, vol. 68, p. 6739.
139. Liard, A., Nguyen, T.-H., Smir, A.I.D., Vaultier, M., Derdour, A., and Mortier, J., Chem. Eur. J., 2003, vol. 9, p. 1000.
140. Mertens, A., Lammertsma, K., Arvanaghi, M., and Olah, G.A., J. Am. Chem. Soc., 1983, vol. 105, p. 5657.
141. Borodkin, G.I., Popov, S.A., and Shubin, V.G., Abstracts of Papers, Int. Conf. "Reaction Mechanisms and Organic Intermediates," St. Petersburg: Nauch.-Issled. Inst. Khim. Sankt-Peterburg Gos. Univ., 2001, p. 87.
142. Borodkin, G.I., Popov, S.A., Pokrovskii, L.M., and Shubin, V.G., Russ. J. Org. Chem., 2003, vol. 39, p. 747.
143. Borodkin, G.I., Elanov, I.R., Popov, S.A., Pokrovskii, L.M., and Shubin, V.G., Russ. J. Org. Chem., 2003, vol. 39, p. 672.
144. Borodkin, G.I., Bessonov, A.A., Popov, S.A., and Shubin, V.G., Materialy Vserossiiskoi nauchnoi molodezhnoi konferentsii "pod znakom sigma" (Proc. All-Russia Scientific Youth Conf. "Under the Sigma Sign"), Omsk, 2003, p. 55.
145. Borodkin, G.I., Bessonov, A.A., Andreev, R.V., and Shubin, V.G., Russ. J. Org. Chem., 2004, vol. 40, p. 755.
146. Takeuchi, H., Adachi, T., Nishiguchi, H., Itou, K., and Koyama, K., J. Chem. Soc., Perkin Trans. 1, 1993, p. 867.
147. Olah, G.A. and Ernst, T.D., J. Org. Chem., 1989, vol. 54, p. 1203.
148. Stevens, M.F.G., Shi, D.-F., and Castro, A., J. Chem. Soc., Perkin Trans. 1, 1996, p. 83.
149. Takeuchi, H. and Watanabe, K., J. Phys. Org. Chem., 1998, vol. 11, p. 478.
150. Abramovitch, R.A. and Shi, Q., Heterocycles, 1994, vol. 38, p. 2147.
151. Abramovitch, R.A., Ye, X., Pennington, W.T., Schimek, G., and Bogdal, D., J. Org. Chem., 2000, vol. 65, p. 343.
152. Abramovitch, R.A. and Ye, X., J. Org. Chem., 1999, vol. 64, p. 5904.
153. Abramovitch, R.A., Miller, J., and Souza, A.J.C., Tetrahedron Lett., 2003, vol. 44, p. 6965.
154. Lang, S., Kennedy, A.R., Murphy, J.A., and Payne, A.M., Org. Lett., 2003, vol. 5, p. 3655.
155. Zaltsgendler, I., Leblanc, Y., and Bernstein, M.A., Tetrahedron Lett., 1993, vol. 34, p. 2441.
156. Mitchell, H. and Leblanc, Y., J. Org. Chem., 1994, vol. 59, p. 682.
157. Leblanc, Y. and Boudreault, N., J. Org. Chem., 1995, vol. 60, p. 4268.
158. Dufresne, C., Leblanc, Y., Berthelette, C., and McCooeye, C., Synth. Commun., 1997, vol. 27, p. 3613.
159. Bombek, S., Lenarsic, R., Kocevar, M., Saint-Jalmes, L., Desmurs, J.-R., and Polanc, S., Chem. Commun., 2002, p. 1494.
160. Lenarsic, R., Kocevar, M., and Polanc, S., J. Org. Chem., 1999, vol. 64, p. 2558.
161. Yadav, J.S., Reddy, B.V.S., Kumar, G.M., and Madan, C., Synlett, 2001, p. 1781.
162. Yadav, J.S., Reddy, B.V.S., Veerendhar, G., Rao, R.S., and Nagaiah, K., Chem. Lett., 2002, p. 318.
163. Kikugawa, Y., Aoki, Y., and Sakamoto, T., J. Org. Chem., 2001, vol. 66, p. 8612.
164. Ohwada, A., Li, H., Sakamoto, T., and Kikugawa, Y., Heterocycles, 1997, vol. 46, p. 225.
165. Ohwada, A., Nara, S., Sakamoto, T., and Kikugawa, Y., J. Chem. Soc., Perkin Trans. 1, 2001, p. 3064.
166. Takeuchi, H., Chem. Commun., 1987, p. 961.
167. Abramovitch, R.A., Evertz, K., Huttner, G., Gibson, H.H., and Weems, H.G., Chem. Commun., 1988, p. 325.
168. Takeuchi, H., Hayakawa, S., and Murai, H., Chem. Commun., 1988, p. 1287.
169. Takeuchi, H. and Koyama, K., J. Chem. Soc., Perkin Trans. 1, 1988, p. 2277.
170. Takeuchi, H., Hayakawa, S., Tanahashi, T., Kobayashi, A., Adachi, T., and Higuchi, D., J. Chem. Soc., Perkin Trans. 2, 1991, p. 847.
171. Takeuchi, H., Higuchi, D., and Adachi, T., J. Chem. Soc., Perkin Trans. 1, 1991, p. 1525.
172. Abramovitch, R.A. and Shi, Q., Heterocycles, 1994, vol. 37, p. 1463.
173. Srivastava, S., Kercher, M., and Falvey, D.E., J. Org. Chem., 1999, vol. 64, p. 5853.
174. Takeuchi, H., Taniguchi, T., Masuzawa, M., and Isoda, K., J. Chem. Soc., Perkin Trans. 2, 1998, p. 1743.
175. Bogdal, D., Heterocycles, 2000, vol. 53, p. 2679.
176. Chiapperino, D., McIlroy, S., and Falvey, D.E., J. Am. Chem. Soc., 2002, vol. 124, p. 3567.
177. McIlroy, S., Moran, R.J., and Falvey, D.E., J. Phys. Chem. A, 2000, vol. 104, p. 11154.
178. McIlroy, S. and Falvey, D.E., J. Am. Chem. Soc., 2001, vol. 123, p. 11329.
179. Beres, M., Hajos, G., Riedl, Z., Soos, T., Timari, G., and Messmer, A., J. Org. Chem. 1999, vol. 64, p. 5499.
180. Bogdal, D., ARKIVOC, 2001, vol. 6, p. 109.
181. Andreev, R.V., Borodkin, G.I., Gatilov, Yu.V., Shakirov, M.M., and Shubin, V.G., Russ. J. Org. Chem., 2004, vol. 40, p. 567.
182. Nefedov, V.D., Toropova, M.A., Simonova, T.P., Avrorin, V.V., and Vorontsov, A.M., Zh. Org. Khim., 1990, vol. 26, p. 1133.
183. Nefedov, V.D., Toropova, M.A., Simonova, T.P., Avrorin, V.V., and Kaso Pen'ya, R., Zh. Org. Khim., 1992, vol. 28, p. 2272.
184. Simonova, T.P., Nefedov, V.D., Toropova, M.A., Avrorin, V.V., and Kirillov, N.F., Russ. J. Org. Chem., 1995, vol. 31, p. 1499.