Secondary amides as ortho-directed metallation groups for arenes; a useful construction way of the polysubstituted aromatic and heteroaromatic system

Current Organic Chemistry

Volumn 10, Issue 14, 2006, Pages 1817-1848

  Epsztajn, Jan ^a   Jóźwiak, Andrzej ^a   Szcześniak, Aleksandra K ^a  

^a UNIVERSITY OF LODZ   (Poland)

Author keywords

Amide metallation; Lithiation electrophilic substitution sequence; N methylisonicotinamide; Single electron transfer; Tetrahydrofuran

Indexed keywords

AMIDES; AROMATIZATION; CARBOXYLIC ACIDS;

AMIDE METALLATION; ELECTROPHILIC SUBSTITUTIONS; LITHIATION; LITHIATION ELECTROPHILIC SUBSTITUTION SEQUENCE; METALLATION; N-METHYLISONICOTINAMIDE; SECONDARY AMIDES; SINGLE ELECTRON TRANSFER; TETRA-HYDROFURAN; TETRAHYDROFURANS;

AROMATIC COMPOUNDS;

1 OXO 3,3 DIPHENYL 1,3 DIHYDROISONENZOFURAN 5 CARBOXYLIC ACID METHYLAMIDE; 2 BEZOYLNICOTINIC ACID; 2 BROMO 4 CHLOROBENZANILIDE; 3 HDYROXYPIROLOPYRIDINE DERIVATIVE; 3 HYDROXY 4 ARYLISOCHROMAN DERIVATIVE; 3 HYDROXYIZOINDOLINONE DERIVATIVE; 3,5 BISTRIMETHYLSILANYLPYRIDAZINE 4 CARBOXYLIC ACID TERTBUTYLAMIDE; 4 BEZOYLNICOTINIC ACID; 5 (HYDROXYPHENYLMETHYL)PYRIDAZINE 4 CARBOXYLIC ACID BENZYLAMIDE; AMIDE; ANTIBIOTIC AGENT; AROMATIC CARBOXYLIC ACID; AROMATIC COMPOUND; AURAMINE; BENZOIC ACID DERIVATIVE; BERNINAMYCINE; BERNINAMYCINIC ACID; COUMARIN DERIVATIVE; EUPOAURAMINE; HEXAHYDROBENZO[C]PHENANTHRENEDIOL DERIVATIVE; INDOLE DERIVATIVE; ISOCHROMAN DERIVATIVE; ISOCOUMARIN DERIVATIVE; LITHIUM; NICOTINIC ACID DERIVATIVE; OXAZOLINE DERIVATIVE; PHTHALIDE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALKYLATION; CARBONYLATION; CHEMICAL PROCEDURES; HYDROXYLATION; LITHIATION; METALLATION; METHODOLOGY; REVIEW; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33748498246     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527206778249883     Document Type: Review

References (132)

1. Smith, M. B.; March, J. March's Advanced Organic Chemistry, Reactions, Mechanisms, and Structure, Fifth Edition, John Wiley & Sons, Inc. 2001.
2. Gilman, H.; Bebb, R.L. J Am. Chem. Soc., 1939, 61, 109.
3. Wittig, G.; Fuhrman, G. Chem. Ber., 1940, 13, 1197.
4. Gilman, H.; Morton, J. W. Org. React. (N.Y.) 1954, 8, 258.
5. Puterbaugh, W. H.; Hauser, C. R. J. Org. Chem., 1964, 29, 853.
6. Slocum, D. W.; Sugarman, D. I. Adv. Chem. Ser., 1974, No. 130, 227.
7. Gschwend, H. W.; Hamdan, A. J. Org. Chem., 1975, 40, 2008.
8. Meyers, A. I.; Mihelich, E. D. J. Org. Chem., 1975, 40, 3158.
9. Beak, P.; Brown, R. A. J. Org. Chem., 1977, 42, 1823.
10. Snieckus, V. Chem. Rev., 1990, 90, 970.
11. Schlosser M. Structure und Reaktivitat Polar Organometalle, Springer-Verlag, Berlin 1973.
12. Wakefield, B. J. The Chemistry of Organolithium Compounds, Pergamon Press, New York, 1974.
13. Gschwend, H. W.; Rodriguez H. R. Org. React. (N.Y.), 1979, 26, 1.
14. Setzer, W. N.; Schleyer, P. v. R. Adv. Organomet. Chem., 1995, 24, 353.
15. Brandsma, L. In Houben-Weyl, Methoden der Organischen Chemie, vol. E19d (Dd. Hanack, M.) Thieme Verlag Stuttgart, 1993, pp. 369.
16. Klumpp, G. Recl. Trav. Chim. Pays-Bas, 1986, 105, 1.
17. Beak, P.; Meyers, A. I. Acc. Chem. Res., 1986, 19, 356.
18. Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem. Int. Ed., 2004, 43, 2206.
19. Schlosser, M.; Mongin, F.; Porwisiak, J.; Dmowski, W.; Büker, H. H.; Nibbering, N. M. M. Chem. Eur. J., 1998, 4, 1281.
20. Schlosser M. Angew. Chem. Int. Ed., 1998, 37, 1497.
21. Maggi, R.; Schlosser, M. Tetrahedron Lett., 1999, 40, 8797.
22. Snieckus, V. Heterocycles, 1980, 14, 1649.
23. Beak, P.; Snieckus, V. Acc. Chem. Res., 1982, 10, 306.
24. Narasimhan, N. S.; Mali, R. S. Synthesis, 1983, 957.
25. Narasimhan, N. S.; Mali, R. S. Top. Curr. Chem., 1987, 138, 63.
26. Reumon, M; Meyers, A. J. Tetrahedron, 1985, 41, 837.
27. Hartung, C. G.; Snieckus, V. In Moder Arene Chemistry (Ed. Astruc, D.), Wiley-VCH Verlag GmbH Br KgaA, Weinheim, 2002, pp. 330.
28. Eikema Hommes, N. J. R.; Schleyer, P. v. R. Angew. Chem. Int. Ed., 1992, 31, 755.
29. Eikema Hommes, N. J. R.; Schleyer, P. v. R. Tetrahedron, 1994, 50, 5903.
30. Chadwick, S. T.; Rennels, R. A.; Rutherford, J. L.; Collum, D. B. J. Am. Chem. Soc., 2000, 122, 8640.
31. Arvidsson, P. I.; Hilmersson, G.; Davidsson Ö. Helv. Chim. Acta, 2002, 85, 3914.
32. Arvidsson, P. I.; Hilmersson, G.; Davidsson Ö. Chem.-Eur. J., 1999, 5, 2348.
33. Arvidsson, P. I.; Davidsson, Ö.; Hilmersson, G. Tetrahedron Asymmetry, 1990, 10, 527.
34. Brown, T. L. Pure Appl. Chem., 1970, 23, 447.
35. Guthrie, R. D. In Comprehensive Carbanion Chemistry, Part A; Buncel, E., Durst, T., Ed., Elsevier: Amsterdam, 1980, pp. 197.
36. Ashby, E. C.; Pham, T. N. J. Org. Chem., 1987, 52, 1291.
37. Liotta, D.; Saindane, M.; Waykole, L. J. Am. Chem. Soc., 1983, 105, 2922.
38. Arnett, E. M.; Molter, K. E.; Marchot, E. C.; Donovan, W. H.; Smith P. J. Am. Chem. Chem. Soc., 1987, 109, 3788.
39. Yamataka, H.; Fujimura, N.; Kawafuji, Y.; Hanafusa, T. J. Am. Chem. Chem. Soc., 1987, 109, 4305.
40. Slocum, D. W.; Jennings, C. A. J. Org. Chem., 1976, 41, 3653.
41. Beak, P.; Brown, R. A. J. Org. Chem., 1979, 44, 4463.
42. Beak, P.; Brown, R. A. J. Org. Chem., 1982, 47, 34.
43. Beak, P.; Tse, A.; Hawkins, J.; Chen, C.-W.; Mills, S. Tetrahedron, 1983, 39, 1983.
44. Meyers, A. I.; Lutomski, K. J. Org. Chem., 1979, 44, 4464.
45. Ref. 117a, In the Review by Snieckus, V. No citation 10.
46. Iwao, M.; Iihama, T.; Mahalanabis, K. K.; Perrier, H.; Snieckus, V. J. Org. Chem., 1989, 54, 24.
47. Quesnelle, C.; Iihama, T.; Aubert, T.; Perrier, H.; Snieckus, V. Tetrahedron Lett., 1992, 33, 2625.
48. Meyers, A. I.; Avila, W. B. Tetrahedron Lett., 1989, 21, 3335.
49. Epsztajn, J.; Jóźwiak, A.; Krysiak, J. K.; tucka, D. Tetrahedron, 1996, 52, 11025.
50. Beak, P., Kerrick, S. T.; Gallagher, D. J. J. Am. Chem. Soc., 1993, 115, 10628.
51. Ameline, G.; Vaultier, M.; Mortier, J. Tetrahedron Lett., 1996, 37, 8175.
52. Mortier, M.; Vaultier, M. C.R. Acad. Sci. Paris, 1998, 1, Serie II c, 465.
53. Jóźwiak, A.; Brzeziński, J. Z., Ptotka, M. W., Szcześniak, A. K.; Malinowski, Z.; Epsztajn, J. Eur. J. Org. Chem., 2004, 3254.
54. Epsztajn, J.; Bieniek, A.; Kowalska, J. A.; Ścianowski, J. Monatsh. Chem., 1992, 123, 1125.
55. Epsztajn, J.; Bieniek, A.; Kowalska, J. A. Monatsh. Chem., 1996, 127, 701.
56. Epsztajn, J.; Bieniek, A.; Kowalska, J.A. Tetrahedron, 1991, 47, 1697.
57. Epsztajn, J.; Bieniek, A.; Brzeziński, J. Z.; Jóźwiak, A. Tetrahedron Lett., 1983, 24, 4735.
58. Epsztajn, J.; Bieniek, A.; Ptotka, M. W.; Suwald, K. Tetrahedron, 1989, 45, 7469.
59. Slocum, D. W.; Stonemark, F. E. J. Org. Chem., 1973, 38, 1677.
60. Couture, A.; Cornet, H.; Grandclaudon, P. Tetrahedron Lett., 1993, 34, 8097.
61. Fisher, L. E.; Muchowski, J. M.; Clark, R. D. J. Org. Chem., 1992, 57, 2700.
62. Metallinos, C.; Nerdinger, S.; Snieckus, V. Org. Lett., 1999, 1, 1183.
63. McCombie, S.W.; Lin, S.-I.; Vice S.F. Tetrahedron Lett., 1999, 40, 8767.
64. Epsztajn, J.; Bieniek, A.; Ptotka, M. W. J. Chem. Research (S), 1986, 20; J. Chem. Research (M), 1986, 0442.
65. Gore, V. G.; Narasimhan, N. S. J. Chem. Soc. Perkin Trans. I, 1988, 481.
66. Unpublished results from our laboratory.
67. Harder, S.; van Lenthe, J.H.; van Eikema Hommes, N. J. R.; von Ragué Schleyer, P. J. Am. Chem. Soc., 1994, 116, 2508.
68. Bowden, K.; Hiscocks, S. P.; Perjéssy, A. J. Chem. Soc., Perkin Trans. 2, 1998, 291.
69. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
70. Sibi, M. P. Org. Prep. Proced. Int., 1993, 25, 15.
71. Epsztajn, J.; Malinowski, Z.; Brzeziński, J. Z.; Karzatka, M. Synthesis, 2001, 2085.
72. Grimaldi, T.; Romero, M.; Pujol M. D. Synlett, 2000, 1788.
73. Narasimhan, N. S.; Bhide, B. H. Tetrahedron, 1971, 27, 6171.
74. Bhide, B. H.; Narasimhan, N.S. Chem. Ind., 1974, 75.
75. Narasimhan, N. S.; Bhide, B. H. Chem. Commun. 1970, 1552.
76. Bhide, B. H.; Gupta, V. P.; Narasimhan, N. S.; Mali, R. S. Chem. Ind., 1975, 519.
77. Choukchou-Braham, N.; Asakawa, Y.; Lepoittevin J.-P. Tetrahedron Lett., 1994, 35, 3949.
78. Nicolaou, K. C.; Gray D.; Tae, J. Angew. Chem. Int. Ed., 2001, 40, 3675.
79. Bhide, B. H.; Gupta, V. P. Indian J. Chem. [B], 1979, 17, 295.
80. Bhide, B. H.; Shah, K. K. Indian J. Chem. [B], 1980, 19, 9.
81. Bhide, B. H.; Brahmbhatt, D. I.; Shah, K.K. Indian J. Chem. [B], 1981, 20, 831.
82. Bhide, B. H.; Brahmbhatt, D. I. Proc. Indian Acad. Sci., 1980, 89, 525.
83. Bhide, B. H.; Gupta, V. P. Indian J. Chem. [B], 1977, 15, 512.
84. Narasimhan, N. S.; Mali, R. S. Synthesis, 1975, 797.
85. Mali, R. S.; Yeola, S. N. Synthesis, 1986, 755.
86. Rodriguez, H.R., Ciba-Geigy Pharmaceutical Co., Sammit, New Jersey, Unpublished results, in Gschwend, H.W.; Rodriquez, H.R. Org. Reactions, 1979, 26, 55.
87. Epsztajn, J.; Jóźwiak, A; Szcześniak A.K. Tetrahedron, 1993, 49, 929.
88. Epsztajn, J.; Jóźwiak, A.; Krysiak, J. A. Tetrahedron, 1994, 50, 2907.
89. Katritzky, A. R.; Rahimi-Rastgoo, S.; Ponkshe, N. K. Synthesis, 1981, 127.
90. Epsztajn, J.; Jóźwiak, A; Czech, K.; Szcześniak A. K. Monatsh. Chem., 1990, 121, 909.
91. Epsztajn, J.; Jóźwiak, A; Szcześniak A. K. Synthetic Comm., 1994, 24, 1789.
92. Epsztajn, J.; Grzelak, R.; Jóźwiak, A. Synthesis, 1996, 1212.
93. Brzeziński, J. Z.; Bzowski, H. B.; Epsztajn, J. Tetrahedron, 1996, 52, 3261.
94. Narasimhan, N. S.; Ammanamanchi, R. Tetrahedron Lett., 1983, 23, 4733.
95. Lambert, C.; Hilbert, M.; Christiaens, L.; Dereu, N. Synth. Commun., 1991, 21, 85.
96. Laws, M. J.; Schiesser, C.H.; White, J. M.; Zheng, S.-L. Aust. J. Chem., 2000, 53, 277.
97. Snieckus, V.; Beaulieu, F.; Mohri, K.; Han, W.; Murphy, C. K.; Davis, F. A. Tetrahedron Lett., 1994, 35, 3465.
98. Chang, T.-C.; Huang, M.-L.; Hsu, W.-L.; Hwang, J.M.; Hsu, L.-Y. Chem. Pharm. Bull., 2003, 51, 1413.
99. Cipollina, J. A.; Ruediger, E. H.; New, J. S.; Wire, M. E.; Shepherd, T. A.; Smith, D. W.; Yevich, J. P. J. Med. Chem., 1991, 34, 3316.
100. Engman, L.; Hallberg, A. J. Org. Chem., 1989, 54, 2964.
101. Bengtsson, S.; Högberg, T J. Org. Chem., 1989, 54, 4549.
102. Zade, S. S.; Panda, S.; Singh, H. B.; Wolmershäuser, G., Tetrahedron Lett., 2005, 46, 665.
103. Carpenter, A. J.; Chadwick, D. J. J. Org. Chem., 1985, 50, 4362.
104. Rizzi, J. P.; Kende, A. S. Tetrahedron, 1984, 40, 4694.
105. Couture, A., Cornet, H., Grandclaudon, P. Tetrahedron Lett., 1993, 34, 8097.
106. Nicolaou, K. C.; Gray, D.; Tae, J. Angew. Chem. Int. Ed., 2001, 40, 3675.
107. Kelly, R.; Echavarren, A.; Chandrakumar, N. S.; Köksal, Y. Tetrahedron Lett., 1984, 25, 2127.
108. Bieniek, A.; Epsztajn, J., Kowalska, J. A., Malinowski, Z. Tetrahedron Lett., 2001, 42, 9293.
109. Rys, V.; Couture, A.; Deniau, E.; Lebrun, S.; Grandclaudon, P. Synlett, 2004, 12, 2233.
110. Epsztajn, J.; Ptotka, M. W.; Grabowska, A. Synth. Commun., 1997, 27, 1075.
111. Wright, S. W.; Carbertt, R. L. Tetrahedron Lett., 1993, 34, 2875.
112. Fisher, L. E.; Caroon, J. M.; Jahangir; Stabler, S. R.; Lundberg, S.; Muchowski, J. M. J. Org. Chem., 1993, 58, 3643.
113. Pratt, S. A.; Goble, M. P.; Mulvaney, M. J.; Wuts, P. G. M. Tetrahedron Lett., 2000, 41, 3559.
114. Epsztajn, J.; Jóźwiak, A; Szcześniak A. K. J. Chem. Soc., Perkin Trans. 1, 1998, 2563.
115. Micheli, F.; Crippa, L.; Donati, D.; Di Fabio, R.; Leslie, C. Il Farmaco, 2001, 56, 715.
116. Dellacoletta, B. A.; Ligon, Jr. W. J.; Verbicky, Jr, J. W.; Williams, L. J. Org. Chem., 1981, 46, 3923.
117. Johnson, R. E.; Hane, J. T.; Schlegel, D. C.; Perni, R. B.; Herrmann, Jr. J. L.; Opalka, C. J.; Carabateas, P. M.; Ackerman, J. H.; Swestock, J.; Birsner, N. C.; Tatlock, J. H. J. Org. Chem., 1991, 56, 5218.
118. Lyga, J. W.; Meier, G. A. Synth. Commun. 1994, 24, 2491.
119. Potts, K. T.; Bhattacharjee, D.; Walsh, E. B. J. Org. Chem. 1986, 51, 2011.
120. Forbes, I.; Pratt, R. A.; Raphael, R. A. Tetrahedron Lett., 1978, 19, 3965.
121. Rebstock, A.-S.; Mongin, F.; Trecourt F.; Queguiner, G. Tetrahedron Lett., 2002, 43, 767.
122. Lazaar, J.; Rebstock, A.-S.; Mongin, F.; Godard, A.; Trecourt, F.; Marsais, F.; Queguiner, G. Tetrahedron, 2002, 58, 6723.
123. Gu, Y. G.; Bayburt, E. K.; Michaelides, M. R.; Lin, C. W.; Shiosaki, K. Bioorg. Med. Chem. Lett., 1999, 9, 1341.
124. Wright, S. W. J. Heterocycl. Chem., 2001, 38, 723.
125. Lane, C.; Snieckus, V. Synlett, 2000, 1294.
126. Katritzky, A. R.; Nair, S. K.; Rodriguez-Garcia, V.; Xu, Y.-J. J. Org. Chem., 2002, 67, 8237.
127. Uemura, M.; Nishikawa, N.; Hayashi, Y. Tetrahedron Lett., 1980, 21, 2069.
128. Bhide, B. H.; Kalaria, A. J.; Patel, S. K. Indian J. Chem., Sect. B: Org. Che. Incl. Med. Chem., 1999, 38, 971.
129. Campbell, J. B.; Dedinas, R F.; Trumbower-Walsh, S. A. J. Org. Chem., 1996, 61, 6205.
130. Turck, A.; Ple, N.; Mojovic, L.; Ndzi, B.; Queguiner, G.; Haider, N.; Schuller, H.; Heinisch, G. J. Heterocycl. Chem., 1995, 32, 841.
131. Kwon, B.-S.; Tae, J. Heterocycles, 2004, 62, 137.
132. Romero, M.; Pujol, M. D. Synlett, 2003, 173.