Isocyanide based multi component reactions in combinatorial chemistry

Combinatorial Chemistry and High Throughput Screening

Volumn 1, Issue 1, 1998, Pages 1-22

  Dömling, Alexander ^a,b  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b Morphochem AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE; LIDOCAINE;

CHEMICAL MODEL; CHEMISTRY; DRUG DESIGN; HISTORY; METHODOLOGY; REVIEW;

CHEMISTRY, PHARMACEUTICAL; CYANIDES; DRUG DESIGN; HISTORY, 19TH CENTURY; HISTORY, 20TH CENTURY; LIDOCAINE; MODELS, CHEMICAL;

EID: 0032035067     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (166)

1. Lieke, W., Justus Liebigs Ann. Chem., 1859, 112, 316
2. Gautier, A., Ann. Chem. (Paris), 1869, 17, 218.
3. Chang, C. W. J., Scheuerer, P. J., in: Scheuerer, P. J. (ed), Topics in Current Chemistry, 1993, Springer Verlag, New York, 33-77.
4. Ger. Pat. 1,209,798 (1962/1963); U.S. Pat. 3,278,371 (1962/1966); Ger. Pat. 1,235,298 (1964/1967); Ger. Pat. Appl. 1,211,853 (1962/1966); Ger. Pat. 1.215.142 (1964/1966); Brit. Pat. 1,064,835 (1964/1967); Ger. Pat. 1,215.141 (1964/1966).
5. Gautier, A., Ann. Chem., 1867, 142, 289.
6. Ugi, I., Betz, W., Fetzer, U., Offermann, K., Chem. Ber., 1961, 94, 2814.
7. review: Hoffmann, P., Marquarding, D., Kleiimann, H., Ugi, I., In The Chemistry of the Cyano Group, Rappoprt, Z., editor, Wiley, New York, 1970, Chap. 15, 853-883.
8. Ugi, C. Steinbrückner, Ger. 1,103.337, Mar. 30, 1961, Appl Jan.22, 1959: Chemical Abstracts 12503, Vol. 57
9. Lindqvist, K., Sundling, S., "Xylocain - en uppfinning - ett drama - en industri", 1993, publisher by AB Astra.
10. Ugi, I., Steinbrückner, C., Chem. Ber., 1961, 94, 734.
11. Gokel, G., Lüdke, G., Ugi, I., In: Isonitrile Chemistry, Ugi, I, ed. Academic Press, New York, 1971, p.149.
12. Ugi, I., Dömling, A., Hörl, W., Endeavour, 1994, 18, 115; Ugi, I., J. prakt. Chem., 1997, 339, 499.
13. Ugi, I., Dömling, A., Hörl, W., Endeavour, 1994, 18, 115; Ugi, I., J. prakt. Chem., 1997, 339, 499.
14. Laurent, A., Gerhardt, C.F., Ann. Chimie et Physique, 1838, 66, 181.
15. Strecker, A., Ann. Chem., 1850, 75, 27.
16. Dyker, G., Angew. Chem. Int. Ed. Engl., 1997, 36, 1997
17. Ugi, I., Dömling, A., Gruber, B.,unpublished.
18. Dömling, A., Doctoral Thesis, Technische Universität München, 1994.
19. Ugi, I., Dömling, A., Gruber, B., Heilingbrunner, C., Hörl, W., in: Software Development in Chemistry 9, Proceedings of the 9th GDCh-Workshop "Computer in Chemistry", Bitterfeld 1994, Gesellschft Deutscher Chemiker, Frankfurt, 1995, 113.
20. Tempest, P.A., Brown, S.D., Armstrong, R.W., Angew. Chem. Int. Ed. Engl., 1996, 35, 640.
21. Dömling A., Gruber, B., Ugi, I., Poster Presentation at CHI-conference, La Jolla, CA, Januar 23rd - 25th 1995; Ugi, I., Göbel, M., Gruber, B., Heilingbrunner, M., Heiß, C., Hörl, W., Kern, O., Starnecker, M., Dömling A., Res. Chem. Intermed., 1996, 22, 625.
22. Dömling A., Gruber, B., Ugi, I., Poster Presentation at CHI-conference, La Jolla, CA, Januar 23rd - 25th 1995; Ugi, I., Göbel, M., Gruber, B., Heilingbrunner, M., Heiß, C., Hörl, W., Kern, O., Starnecker, M., Dömling A., Res. Chem. Intermed., 1996, 22, 625.
23. Weber, L., Waltbaum, S., Broger, C., Gubernator, K., Angew. Chem. Int. Ed. Engl., 1995, 34, 2280.
24. review: Marquarding, D., Gokel, G., Hoffmann, P., Ugi, I., in Isonitrile Chemistry, Ugi, I. editor, Academic Press, New York, 1971, p. 133-144.
25. Review: Ugi, I., Lohberger, S., Karl, R., In: Comprehensive Organic Chemistry: Selectivity for Synthetic Efficiency, Trost, B., Heathcock, C.H. (editors), Pergamon, Oxford 1991, Vol. 2, p 1083-1109; (a) p. 1090.
26. For a review on multi component heterocycle synthesis using isocyanides see: Marcaccini, S., Torroba, T., Org. Prep. Proced. Int., 1993, 25, 141.
27. Passerini, M., Gazz. Chim. Ital., 1921, 51 11, 126, 181, ibidem 1922, 521, 432; 1923, 53, 331, 410; 1924, 54, 529, 540; 1925, 55, 721; 1926, 56, 826.
28. Passerini, M., Gazz. Chim. Ital., 1921, 51 11, 126, 181, ibidem 1922, 521, 432; 1923, 53, 331, 410; 1924, 54, 529, 540; 1925, 55, 721; 1926, 56, 826.
29. Passerini, M., Gazz. Chim. Ital., 1921, 51 11, 126, 181, ibidem 1922, 521, 432; 1923, 53, 331, 410; 1924, 54, 529, 540; 1925, 55, 721; 1926, 56, 826.
30. Passerini, M., Gazz. Chim. Ital., 1921, 51 11, 126, 181, ibidem 1922, 521, 432; 1923, 53, 331, 410; 1924, 54, 529, 540; 1925, 55, 721; 1926, 56, 826.
31. Passerini, M., Gazz. Chim. Ital., 1921, 51 11, 126, 181, ibidem 1922, 521, 432; 1923, 53, 331, 410; 1924, 54, 529, 540; 1925, 55, 721; 1926, 56, 826.
32. Passerini, M., Gazz. Chim. Ital., 1921, 51 11, 126, 181, ibidem 1922, 521, 432; 1923, 53, 331, 410; 1924, 54, 529, 540; 1925, 55, 721; 1926, 56, 826.
33. Passerini, M., Ragni, G., Gazz. Chim. Ital., 1931, 61, 964.
34. Meyr, R., Ugi, I., Chem. Ber., 1961, 94, 2229.
35. Hagedorn, I., Ugi, I., Chem. Ber., 1965, 98, 936; Ger. Pat., 1,173,082 (1964).
36. Seebach, D., Adam, G., Schiess, M., Weigand, W., Chem. Ber., 1988, 121, 507.
37. Neidlein, R., Z. Naturforsch. B, 1964, 19, 1159.
38. Ugi, I., Rosendahl, F. K., Chem. Ber., 1961, 94, 2233.
39. Kreutzkamp, N., Lämmerhirt, K., Angew. Chem., 1968, 80, 3728.
40. El Gomati, T., Firl, J., Ugi, I., Chem. Ber., 1977, 110, 1603.
41. Capuano, L., Tammer, T., Chem. Ber., 1981, 114, 456.
42. Moore, H. W., Yu, C. C., J. Org. Chem., 1981, 46, 4935.
43. Bock, H., Ugi, I., J. prakt. Chem., 1997, 339, 385.
44. Hagedom, I., Ugi, I., Justus Lienigs Ann. Chem., 1962, 659, 184.
45. Rachon, J., Chimia, 1983, 37, 299.
46. Rachon, J., Synthesis, 1984, 219.
47. Sone, C., Nemoto T., Ojika, M., Yamada, K., Tetrahedron Lett., 1993, 52, 8445.
48. Dömling, A., Heck, S., unpublished; see also: I. Ugi, U. Fetzek, Angew. Chem., 1961, 73, 621.
49. Dömling, A., Heck, S., unpublished; see also: I. Ugi, U. Fetzek, Angew. Chem., 1961, 73, 621.
50. Sebti, S., Foucaud, A., Synthesis, 1983, 546.
51. Bossio, R., Marcaccini, S., Pepino, R., Tetrahedron Lett., 1995, 36, 2325.
52. Bossio, R., Marcaccini, S., Pepino, R., Torroba, T., J. Chem. Soc., Perkin Trans. 1, 1996, 229.
53. Lumma, W. C., J. Org. Chem., 1981, 46, 3668.
54. Falk, J. R., Manna, S., Tetrahedron Lett., 1981, 22, 619.
55. Tempest, P. A., Brown, S. D., Armstrong, R. A., Angew. Chem. Int. Ed. Engl., 1996, 35, 640.
56. Schöllkopf, U., Angew. Chem. Int. Ed. Engl., 1977, 16, 339.
57. Passerini, M., Gazz. Chim. Ital., 1924, 54, 529, 540; Passerini, M., Ragni, G., Gazz. Chim. Ital., 1926, 56, 826, ibidem 1931, 61, 964.
58. Passerini, M., Gazz. Chim. Ital., 1924, 54, 529, 540; Passerini, M., Ragni, G., Gazz. Chim. Ital., 1926, 56, 826, ibidem 1931, 61, 964.
59. Passerini, M., Gazz. Chim. Ital., 1924, 54, 529, 540; Passerini, M., Ragni, G., Gazz. Chim. Ital., 1926, 56, 826, ibidem 1931, 61, 964.
60. Bossio, R., Marcaccini, S., Pepino, R., Polo, C., Torroba, T., Org. Prep. Proced. Int., 1992, 24, 188.
61. Bossio, R., Marcaccini, S., Pepino, R., Liebigs Ann. Chem., 1991, 1107.
62. review: Gokel, G., Lüdke, G., Ugi, I., in Isonitrile Chemistry, Ugi, I. editor, Academic Press, New York, 1971, p. 145-200 and Gokel, G., Hoffman, P., Kleinmann, Klusacek, H., Ludke, G., Marquarding, D., Ugi, I., p 201-216; Lit.
63. review: Gokel, G., Lüdke, G., Ugi, I., in Isonitrile Chemistry, Ugi, I. editor, Academic Press, New York, 1971, p. 145-200 and Gokel, G., Hoffman, P., Kleinmann, Klusacek, H., Ludke, G., Marquarding, D., Ugi, I., p 201-216; Lit.
64. Ugi, I., et al. unpublished.
65. Yamada, T., Nakamura, Y., Miyazawa, T., Kuwata, S., Matsumoto, K., Japan Chem. Express, 1993, 8, 161.
66. Yamada, T., Motoyama, N., Taniguchi, T., Kazuta, T., Miyazawa, T., Kuwata, S., Matsumoto, K., Sugiura, M., Chem. Lett., 1987, 723.
67. Hardy, P.M., Lingham, I.N., Int. J. Protein Res., 1983, 21, 406.
68. Matsumoto, K., Uchida, T., In: Organic Synthesis at High Pressure, Matsumoto, K., Acheson, R.M., editors, Wiley, New York, 1991, p.164.
69. Bowers, M.M., Carroll, P., Joullié, M.M., J. Chem. Soc., Perkin Trans. I, 1989, 857.
70. Fukuyama, T., Robins, B.D., Sachleben, A., Tetrahedron Lett., 1981, 22, 4155.
71. de Laszlo, S.E., Williard, P.G., J. Am. Chem. Soc., 1985, 107, 199.
72. Tsuchida, K., Mizuno, Y., Ikeda, K., Heterocycles, 1981, 15, 883.
73. Tsuchida, K., Ikeda, K., Mizuno, Y., Chem. Pharm. Bull., 1980, 28, 2743.
74. Tsuchida, K., Ikeda, K., Mizuno, Y., Nucleic Acid Res., 1980, 49.
75. Böhm, J.C., Kingsbury, W.D., J. Org. Chem., 1986, 51, 2307.
76. Natchev, I.A., Tetrahedron, 1988, 44, 1511.
77. Immer, H., Nelson, V., Robinson, W., Götz, M., Justus Liebigs Ann. Chem., 1973, 1789.
78. Polyakov, A.J., Aseeve, N.M., Bezrukova, V.G., Izv. Akad. Nauk SSSR Ser. Khim., 1974, 7, 1597.
79. Sutherlin, D.P., Stark, T.M., Hughes, R., Armstrong, R.W., J. Org. Chem., 1996, 61, 8450.
80. Park, W.K.C., Auer, M., Jaschke, H., Wong, C.H., J. Am. Chem. Soc., 1996, 118, 10150.
81. Dömling, A., Richter, W., Ugi, I., Nucleosides & Nucleotides, 1997, 16, 1753-1756.
82. Ugi, I., Croat. chem. Acta, in press.
83. Lack, O., Weber, L., Chimia, 1996, 50, 445.
84. Xiaodong, C., Lio, A., Ohashi, C., Mjalli, A.M.M., Bioorg. Med. Chem. Lett., 1995, 5, 2953.
85. Keating, T.A., Armstrong, R.W., J. Am. Chem. Soc., 1995, 117, 7842.
86. Keating, T.A., Armstrong, R.W., J. Am. Chem. Soc., 1996, 118, 2574.
87. Obrecht, D., Abrecht, C., Grieder, A., Villalgordo, J.M., Helv. Chem. Acta, 1997, 80, 65.
88. Ugi, I., Kaufhold, G., Liebigs Ann. Chem., 1967, 709, 11.
89. Ugi, I., Marquarding, D., Urban, R., Chemistry oand Biochemistry of Amino Acids, Peptides and Proteins, Weinstein, B., editor, Marcel Dekker, New York, 1982, Vol. 6, pp 245
90. Ugi, I., Rec. Chem. Prog., 1969, 30, 289.
91. Demharter, A., Ugi, I., J. Pract. Chem., 1993, 335, 244.
92. Kunz, H., Pfrengle, W., Rück, K., Sager, W., Synthesis, 1991, 1039.
93. Kunz, H., Pfrengle, W., J. Am. Chem. Soc., 1988, 110, 651.
94. Göbel, M., Ugi, I., Synthesis, 1991, 1095.
95. Lehnhof, S., Göbel, M., Karl, R.M., Klösel, R., Ugi, I., Angew. Chem. Int. Ed. Engl., 1995, 34, 1104.
96. Dömling, A., International Conference: Nucleic Acids and Related Macromolecules: Synthesis, Structure, Function and Applications, Ulm, Germany, September 4 - 9, 1997; Dömling Ugi, et al. German-Polish Workshop on Multi Component Reactions & Combinatorial Chemistry, Rzeszów, Poland, September 28 - 30.1997; Dömling, A., Nucleosides & Nucleotides, 1998, in press.
97. Dömling, A., International Conference: Nucleic Acids and Related Macromolecules: Synthesis, Structure, Function and Applications, Ulm, Germany, September 4 - 9, 1997; Dömling Ugi, et al. German-Polish Workshop on Multi Component Reactions & Combinatorial Chemistry, Rzeszów, Poland, September 28 - 30.1997; Dömling, A., Nucleosides & Nucleotides, 1998, in press.
98. Dömling, A., International Conference: Nucleic Acids and Related Macromolecules: Synthesis, Structure, Function and Applications, Ulm, Germany, September 4 - 9, 1997; Dömling Ugi, et al. German-Polish Workshop on Multi Component Reactions & Combinatorial Chemistry, Rzeszów, Poland, September 28 - 30.1997; Dömling, A., Nucleosides & Nucleotides, 1998, in press.
99. Dömling, A., Barrer, M., Richter, W., Starnecker, M., manuscript in preparation.
100. Arshady, K., Ugi, I., et al. Polymer, 1990, 31, 1164.
101. Short, K.M., Ching, B.W., Mjalii, A.M.M., Tetrahedron Lett., 1996, 37, 7489.
102. McFarland, J.W., J. Org. Chem., 1963, 28, 2179.
103. Ugi, I., Angew. Chem. Int. Ed. Engl. 1962, 1, 8; 1982, 21, 810.
104. Ugi, I., Angew. Chem. Int. Ed. Engl. 1962, 1, 8; 1982, 21, 810.
105. Groß, H., Goedle, J., Keitel, I., Dunath, D., J. Prakt. Chem., 1968, 37, 192.
106. Yamada, T., Yanagi, T., Omote, Y., Miyazawa, T., Kuwata, S., Sugiura, M., Matsumoto, K., Japan Chem. Express., 1991, 6, 575.
107. Ugi, I., Wischhofer, E., Chem. Ber., 1962, 95, 136.
108. Schutz, A., Ugi, I., Kabbe, H.F., J. Chem. Res., 1979, (S) 157, and (M) 2064.
109. Schutz, A., Ugi, I., Kabbe, H.F., J. Chem. Res., 1979, (S) 157, and (M) 2064.
110. Ugi, I. Eckert, H., Natural Product Chemistry, Vol. 12 (ed. Attaur-Rahman), Elsevier Science Publishers, Amsterdam, The Netherland, p. 113.
111. Schutz, A., Ugi, I., Z. Naturforsch., 1979, 34b, 1303.
112. Neyer, G., Ugi, I., Synthesis, 1991, 743.
113. Kehagia, K., Ugi, I., Tetrahedron, 1995, 51, 9523.
114. Review: Ugi, I., Angew. Chem. Int. Ed. Engl., 1982, 21, 810.
115. Isenring, H. P., Hofheinz, W., Synthesis, 1981, 385; ibidem Tetrahedron, 1983, 39, 2591.
116. Isenring, H. P., Hofheinz, W., Synthesis, 1981, 385; ibidem Tetrahedron, 1983, 39, 2591.
117. For a review: Cole, D.C., Tetrahedron, 1994, 50, 9517.
118. Adlington, E.M., Baldwin, J.E., Chen, B., Cooper, S.L., McCoull, W.M., Britchard, G.J., Howe, T.J., Becker, C.W., Hermann, R.B., McNulty, A.M., Neubauer, A.C. Bioorg. Med. Chem. Lett., 1997, 7, 1689.
119. Dömling, A., Starnecker, M., Ugi, I., Angew. Chem. Int. Ed. Engl., 1995, 34, 2238.
120. Dömling, A., Kehagia, K., Ugi, I., Tetrahedron, 1995, 51, 9523.
121. Ugi, I., Fetzer, U., Steinbrückner, C., Angew. Chem., 1959, 71, 386.
122. Demharter, A., Hörl, W., Herdtweck, E., Ugi, I., Angew. Chem. Int. Ed. Engl., 1996, 35, 173.
123. Hörl, W., Doctoral Thesis, Technische Universität München, 1996.
124. Hayashi, K., Nunami, K., Kato, J., Yoneda, N., Kubo, M., Ochiai, T., Ishida, J. Med. Chem., 1989, 32, 289.
125. Ugi, I., Demharter, A., Hörl, W., Schmid, T., Tetrahedron, 1996, 52, 11657.
126. Schmid, T., Ugi, I., J. Pract. Chem., 1997, 339, in press.
127. Hatam, M., Tehranfar, D., Martens, J., Synthesis, 1994, 619.
128. http://c2h5oh.org.chemie.tu-muenchen.de/persons/almstetter/index.html.
129. Ugi, I., Hörl, W., Hanusch-Kompa, C., Schmid, T., Herdtweck, E., Heterocycles, 1998, in press.
130. Failli, A., Immer, H., Götz, M., Can. J. Chem., 1979, 57, 3257.
131. Natchev I. A., Tetrahedron, 1988, 44, 1511.
132. Short, K. M., Mjalli, A. M. M., Tetrahedron Lett, 1997, 38, 359.
133. Short, K. M., Ching, B.W., Mjalli, A. M. M., Tetrahedron, 1997, 53, 6653.
134. Harriman, G. C. B., Tetrahedron Lett., 1997, 38, 5591.
135. Ugi, I., Achatz, J., Baumgartner-Rupnik, M., Danzer, B., Fleck, C., Glahsl, G., Herrmann, R., Jacob, P., Kambach, C., et al., Nat. Prod. Chem., 1988, 3, 107; see also [145a].
136. Gross, J. Gloede, I. Keitel, D. Kunath, Jour. f. prakt. Chem., 1968, 37, 192.
137. Ugi, I., Hanusch, C., Tetrahedron Lett, 1997, submitted.
138. Rossen, K., Sager, J., DiMichele, L. M., Tetrahedron Lett., 1997, 38, 3183.
139. Hanusch-Kompa, C., Ugi, I., Tetrahedron Lett. in press.
140. von Zychlinsky, S., Ugi, I., Jour. f. prakt. Chem., 1997, submitted.
141. Bossio, R., Marcos, C. F., Marcaccini, S., Pepino, R., Heterocycles, 1997, 45, 1589.
142. Bossio, R., Marcaccini, S., Paoli, P., Pepino, R., Polo, C., Synthesis, 1991, 999.
143. Ugi, I., Rosendahl, F.K., Liebigs. Ann. Chem., 1963, 666, 65.
144. Hatanaka, M., Ishimaru, T., Tetrahedron Lett., 1981, 22, 3883.
145. Isenring, H.P., Hofheinz, W., Tetrahedron, 1983, 39, 2591.
146. Geller, J., Ugi, I., Chem. Scr., 1983, 22, 65.
147. Grehn, L., Ragnarrson, U., Angew. Chem., Int. Ed. Engl., 1975, 14, 818.
148. Grehn, L., Gunnarsson, K., Ragnarrson, U., Acta Chem. Scand., Ser. B., 1986, 40, 745.
149. Neyer, G., Achatz, J., Danzer, B., Ugi, I., Heterocycles, 1990, 30, 863.
150. Keating, T.A., Armstrong, R.W., J. Am. Chem. Soc., 1995, 117, 7842.
151. Fleck C., PhD Thesis, Technische Universität München, 1990.
152. Hoyng, C.F., Patel., A.D., Tetrahedron Lett, 1980, 21, 4795.
153. Hoyng, C.F., Patel., A.D., J. Chem. Soc., Chem. Commun., 1981, 491.
154. Mjalli, A.M.M., Sharshar, S., Baiga, T., Tetrahedron Lett, 1996, 37, 2943.
155. Stracker, A.M., Keating, T.A., Tempest, P.A., Armstrong, R.W., Tetrahedron Lett., 1996, 37, 1149.
156. Keating, T.A., Armstrong, R.W., J. Am. Chem. Soc., 1996, 118, 2574.
157. Dömling, A., unpublished.
158. Zhang, C., Moran, E.J., Woiwode, T.F., Short, K.M., Mjalli, A.M.M., Tetrahedron Lett., 1996, 37, 751.
159. Keating, T.A., Armstrong, R.W., J. Org. Chem., 1996, 61, 8953.
160. Szardenings, K., International Symposium, Combinatorial Chemistry: New Developments and Applications in Drug Discovery, Schliersee, Germany, October 16 - 18, 1996.
161. Review: Balkenhohl, T., Busch-Hunnenfeld, C., Lansky, A., Zechel, C., Angew. Chem. Int. Ed. Engl., 1996, 35, 2288; (a) 2299.
162. Zychlinsky, S., Cholukovsky, A., Ugi, I., unpublished.
163. Dömling, A., Ugi, I., Angew. Chem. Int. Ed. Engl., 1993, 32, 563.
164. Dömling, A., Herdtweck, K., Ugi, I., Acta Chim. Scand., 1997, in press.
165. Gewald, K., Z. Chem., 1962, 2, 305.
166. Dömling, A., unpublished.