Multicomponent reactions with isocyanides

Angewandte Chemie - International Edition

Volumn 39, Issue 18, 2000, Pages 3168-3210

  Dömling, Alexander ^a   Ugi, Ivar ^b  

^a Morphochem AG   (Germany)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Combinatorial chemistry; Isocyanides; Multicomponent reactions; Synthetic methods

Indexed keywords

ARTICAINE; BUPIVACAINE; BUTANILICAINE; CYANIDE; ISOCYANIC ACID DERIVATIVE; ISOCYANIDE DERIVATIVE; LIDOFENIN; MEPIVACAINE; NATURAL PRODUCT; PRILOCAINE; PYRROCAINE; TOCAINIDE; TRIMECAINE; UNCLASSIFIED DRUG;

CHEMICAL REACTION; DRUG INDUSTRY; DRUG MANUFACTURE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; REVIEW; STRUCTURE ANALYSIS;

EID: 2542509173     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000915)39:18<3168::aid-anie3168>3.0.co;2-u     Document Type: Review

References (397)

1. a) R. B. Woodward, M. P. Cava, W. D. Ollis, H. Hunger, H. U. Daeniker, K. Schenker, J. Am. Chem. Soc. 1954, 76, 4749;
2. b) P. Magnus, M. Giles, Bonnert, C. S. Kim, L. McQuire, A. Merritt, N. Vicker, J. Am. Chem. Soc. 1992, 114, 4403;
3. c) S. D. Knight, L. E. Overman, G. Pairaudeau, J. Am. Chem. Soc. 1993, 115, 9293;
4. d) M. E. Kuehne, F. Xu, J. Org. Chem. 1993, 58, 7490;
5. e) V. H. Rawahl, Iwasa, J. Org. Chem. 1994, 59, 2685.
6. "Towards the ideal synthesis": P. A. Wender, S. T. Handy, D. L. Wright, Chem. Ind. 1997, 765.
7. G. Hellmann, H. Opitz, α-Aminoalkylierung, Verlag Chemie, Weinheim, 1961.
8. I. Ugi, C. Steinbrückner, DE-B 1,103,337, 1959.
9. At the time, the term "collections of compounds" was used instead of "libraries".
10. J. Drews, Die verspielte Zukunft, Birkhäuser, Basel, 1998.
11. I. Ugi, C. Steinbrückner, Chem. Ber. 1961, 94, 734.
12. Other new reviews: a) I. Ugi, A. Dömling, W. Hörl, Endeavour 1994, 18, 430;
13. b) R. W. Armstrong, A. P. Combs, P. A. Tempest, S. D. Brown, T. A. Keating, Acc. Chem. Res. 1996, 29, 123;
14. c) I. Ugi, J. Prakt. Chem. 1997, 339, 499;
15. d) I. Ugi, M. Almstetter, H. Bock, A. Dömling, B. Ebert, B. Gruber, C. Hanusch, S. Heck, K. Kehagia-Drikos, K. Lorenz, S. Papathoma, R. Raditschnig, T. Schmid, B. Werner, A. Von Zychlinski, Croat. Chem. Acta 1998, 71, 527;
16. e) I. Ugi, Proc. Estonian Acad. Sci. Chem. 1998, 47, 107;
17. f) A. Dömling, Comb. Chem. High Through. Screen. 1999, 1, 1;
18. g) S. L. Dax, J. L. McNally, M. A. Youngman, Curr. Med. Chem. 1999, 6, 255;
19. h) A. Dömling, Curr. Opin. Chem. Biol. 2000, 4, 318.
20. a) M. Tramontoni, L. Angiolini, Mannich Bases - Chemistry and Uses, CRC Press, Boca Raton, 1994;
21. b) H. J. Roth, Pharm. Unserer Zeit 1997, 26, 299.
22. M. Arend, B. Westermann, N. Risch, Angew. Chem. 1998, 110, 1096; Angew. Chem. Int. Ed. Engl. 1998, 37, 1044.
23. M. Arend, B. Westermann, N. Risch, Angew. Chem. 1998, 110, 1096; Angew. Chem. Int. Ed. Engl. 1998, 37, 1044.
24. A. Strecker, Liebigs Ann. Chem. 1850, 75, 27.
25. A. Laurent, C. F. Gerhardt, Ann. Chimie Phys. 1838, 66, 181.
26. R. Robinson, J. Chem. Soc. (London) 1917, 111, 876.
27. a) C. Schöpf, Angew. Chem. 1937, 50, 779;
28. b) C. Schöpf, Angew. Chem. 1937, 50, 797.
29. A. Hantzsch, Justus Liebigs Ann. Chem. 1882, 215, 1.
30. I. Gatterman, T. Wieland, Die Praxis der Organischen Chemie, 43th ed., Walter De Gruyter, Berlin, 1982.
31. a) F. Bossert, W. Vater, Naturwissenschaften 1971, 58, 578;
32. b) F. Bossert, H. Meyer, R. Wehinger, Angew. Chem. 1981, 93, 755; Angew. Chem. Int. Ed. Engl. 1981, 20, 762.
33. b) F. Bossert, H. Meyer, R. Wehinger, Angew. Chem. 1981, 93, 755; Angew. Chem. Int. Ed. Engl. 1981, 20, 762.
34. a) M. Passerini, Gazz. Chim. Ital. 1921, 51, 126;
35. b) M. Passerini, Gazz. Chim. Ital. 1921, 51, 181.
36. a) M. Passerini, Gazz. Chim. Ital. 1922, 52, 432;
37. b) M. I. S. Dewar, Electronic Theory of Organic Chemistry, Clarendon, Oxford, 1949, p. 116;
38. c) R. H. Baker, D. Stanonis, J. Am. Chem. Soc. 1951, 73, 699;
39. d) I. Hagedorn, U. Eberholz, H. D. Winkelmann, Angew. Chem. 1994, 76, 583; Angew. Chem. Int. Ed. Engl. 1964, 3, 647;
40. d) I. Hagedorn, U. Eberholz, H. D. Winkelmann, Angew. Chem. 1994, 76, 583; Angew. Chem. Int. Ed. Engl. 1964, 3, 647;
41. e) T. Carfiglio, P.G. Cozzi, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Organometallics 1993, 12, 2726;
42. f) D. Seebach, G. Adam, T. Gees, M. Schiess, W. Weigand, Chem. Ber. 1988, 121, 507.
43. a) H. Bergs, DE-B 566,094,1929;
44. b) T. Bucherer, H. Barsch, J. Prakt. Chem. 1934, 140, 151.
45. a) B. Radziszewski, Ber. Dtsch. Chem. Ges. 1882, 15, 1499;
46. b) B. Radziszewski, Ber. Dtsch. Chem. Ges. 1882, 15, 2706.
47. A. Hantzsch, Ber. Dtsch. Chem. Ges. 1890, 23, 1474.
48. a) P. Biginelli, Ber. Dtsch. Chem. Ges. 1891, 24, 1317, 2962;
49. b) P. Biginelli, Ber. Dtsch. Chem. Ges. 1893, 26, 447.
50. P. Biginelli, Ber. Dtsch. Chem. Ges. 1893, 26, 447.
51. C. Mannich, W. Kröschl, Arch. Pharm. 1912, 250, 647.
52. S. Kubik, R. S. Meissner, J. Rebek, Tetrahedron Lett. 1994, 36, 6635.
53. Carbon monoxide, which is isolobal with isocyanides, also contains a formally divalent carbon. The carbon atom in carbenes is divalent. too. However, most carbenes are extremely short-lived compounds.
54. J. U. Nef, Justus Liebigs Ann. Chem. 1892, 270, 267; J. U. Nef, Justus Liebigs Ann. Chem. 1899, 309, 126.
55. J. U. Nef, Justus Liebigs Ann. Chem. 1892, 270, 267; J. U. Nef, Justus Liebigs Ann. Chem. 1899, 309, 126.
56. Reviews: a) P.J. Scheuer, Acc. Chem. Res. 1992, 25, 433-439;
57. b) M. S. Edenborough, R. B. Herbert, Nat. Prod. Rep. 1988, 5, 229-245.
58. a) I. Ugi, U. Fetzer, W. Unterstenhöfer, P. E., Behrenz, P. E. Frohberger, H. Schinpflug, G. Unterstenhöfer (Bayer AG), DE-B 1,209,798, 1962/1966;
59. b) U. Fetzer, I. Ugi, G. Unterstenhöfer (Bayer AG), DE-B 1,235,298, 1964/1967;
60. c) U. Eholzer, U. Fetzer, I. Ugi, I. Hammann, G. Unterstenhöfer (Bayer AG), DE-B 1,215,141, 1964/1966;
61. d) H. L. Yale (E.R. Squibb and Son, Inc.), US-A 1970.000098106, 1970.
62. The diisocyanide xanthocillin was commercially available as a topic antibiotic (Arzneimittelwerk Dresden).
63. N. Fusetani, Curr. Org. Chem. 1997. 1, 127.
64. W. Lieke, Justus Liebigs Ann. Chem. 1859, 112, 316.
65. A. Gautier, Ann. Chem. (Paris) 1869, 17, 218.
66. A. Demhardter, C. Fleck, personal communication.
67. 1l).
68. A. Gautier, Justus Liebigs Ann. Chem. 1869, 146, 119.
69. Reviews of isocyanides: a) C. Grundman, Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952 -, Vol. E5, 1985, p. 1611;
70. b) I. A. O'Neil in Comprehensive Organic Functional Group Transformations, Vol. 3 (Eds.: A. R. Katritzky, D. Meth-Cohn, C. W. Rees), Pergamon, Oxford, 1995, p. 963;
71. c) review of fluorinated isocyanides: D. Lentz, Angew. Chem. 1994, 106, 1377; Angew. Chem. Int. Ed. Engl. 1994, 33, 1315;
72. c) review of fluorinated isocyanides: D. Lentz, Angew. Chem. 1994, 106, 1377; Angew. Chem. Int. Ed. Engl. 1994, 33, 1315;
73. d) P. Hoffmann, G. Gokel, D. Marquarding, I. Ugi in Isonitrile Chemistry (Ed.: 1. Ugi), Academic Press, New York, 1971, p. 9.
74. a) G. Skorna, I. Ugi, Angew. Chem. 1977, 89, 267; Angew. Chem. Int. Ed. Engl. 1977, 16, 259;
75. a) G. Skorna, I. Ugi, Angew. Chem. 1977, 89, 267; Angew. Chem. Int. Ed. Engl. 1977, 16, 259;
76. b) H. Eckert, B. Forster, Angew. Chem. 1987, 99, 927; Angew. Chem. Int. Ed. Engl. 1987, 26, 1221.
77. b) H. Eckert, B. Forster, Angew. Chem. 1987, 99, 927; Angew. Chem. Int. Ed. Engl. 1987, 26, 1221.
78. R. Obrecht, R. Herrmann, I. Ugi, Synthesis 1985, 400.
79. G. Giesemann, E. von Hinrichs, I. Ugi, J. Chem. Res (S) 1982, 79.
80. A. Gautier, Ann. Chem. (Paris) 1869, 17, 193; A. Gautier, Ann. Chem. (Paris) 1869, 17, 203.
81. A. Gautier, Ann. Chem. (Paris) 1869, 17, 193; A. Gautier, Ann. Chem. (Paris) 1869, 17, 203.
82. + → RNH-RNHCHO).
83. R. Karl, P. Lemmen, I. Ugi, Synthesis 1989, 718.
84. a) G. Skorna, I. Ugi, Chem. Ber. 1978, 111, 3965;
85. b) R. Ashady, I. Ugi, Z. Naturforsch. B 1981, 36, 1202;
86. c) R. Ashady, I. Ugi, Angew. Chem. 1982, 94, 367; Angew. Chem. Int. Ed. Engl. 1982, 21, 374;
87. c) R. Ashady, I. Ugi, Angew. Chem. 1982, 94, 367; Angew. Chem. Int. Ed. Engl. 1982, 21, 374;
88. d) Angew. Chem. Suppl. 1982, 761;
89. e) R. Ashady, I. Ugi, Talanta 1984, 31, 842;
90. f) review: R. Ashady, I. Ugi, Polymer 1990, 31, 1164.
91. a) E. Meyer, J. Prakt. Chem. 1866, 147;
92. b) P. Boullanger, G. Descotes, Tetrahedron Lett. 1976, 38, 4327.
93. a) A. Gautier, Justus Liebigs Ann. Chem. 1867, 142, 289;
94. b) an improvement of the silver cyanide method with dicyanoargentates was described: L. B. Engemyr, A. Martinsen, J. Songstad, Acta Chem. Scand. Ser. A 1974, 28, 255.
95. A. W. Hofmann, Justus Liebigs Ann. Chem. 1867, 144, 114.
96. A. W. Hofmann, Ber. Dtsch. Chem. Ges. 1870, 3, 766.
97. a) I. Ugi, R. Meyr, Angew. Chem. 1958, 70, 702;
98. b) I. Ugi, R. Meyr, Chem. Ber. 1960, 93, 239.
99. a) W. P. Weber, G. W. Gokel, I. K. Ugi, Angew. Chem. 1972, 84, 587; Angew. Chem. Int. Ed. Engl. 1972, 11, 530;
100. a) W. P. Weber, G. W. Gokel, I. K. Ugi, Angew. Chem. 1972, 84, 587; Angew. Chem. Int. Ed. Engl. 1972, 11, 530;
101. b) G. W. Gokel, R. P. Widera, W. P. Weber, Org. Synth. 1976, 55, 96.
102. R. Appel, R. Kleistück, K. D. Ziehn, Angew. Chem. 1971, 83, 143; Angew. Chem. Int. Ed. Engl. 1971, 10, 132.
103. R. Appel, R. Kleistück, K. D. Ziehn, Angew. Chem. 1971, 83, 143; Angew. Chem. Int. Ed. Engl. 1971, 10, 132.
104. U. Schöllkopf, Angew. Chem. 1977, 89, 351; Angew. Chem. Int. Ed. Engl. 1977, 16, 339.
105. U. Schöllkopf, Angew. Chem. 1977, 89, 351; Angew. Chem. Int. Ed. Engl. 1977, 16, 339.
106. D. H. R. Barton, T. Bowles, S. Husinec, J. E. Forbes, A. Llobera, A. E. A. Porter, S. Z. Zard, Tetrahedron Lett. 1988, 29, 3343.
107. a) P. G. Gassman, T. L. Guggenheim, J. Am. Chem. Soc. 1982, 104, 5849;
108. b) γ-hydroxy isocyanides are obtained from oxetanes in an analogous way: P. G. Gassman, Tetrahedron Lett. 1985, 26, 4971.
109. I. A. O'Neil, J. Baldwin, Synlett 1990, 603.
110. Y. Kitano, K. Chiba, M. Tada, Tetrahedron Lett. 1998, 39, 1911.
111. H. Bienaymé, Tetrahedron Lett. 1998, 39, 4255.
112. R. Bossio, S. Marcaccini, R. Pepino, Liebigs Ann. Chem. 1990, 935.
113. P. A. Tempest, S. D. Brown, R. W. Armstrong, Angew. Chem. 1996, 108, 689; Angew. Chem. Int. Ed. Engl. 1996, 35, 640.
114. P. A. Tempest, S. D. Brown, R. W. Armstrong, Angew. Chem. 1996, 108, 689; Angew. Chem. Int. Ed. Engl. 1996, 35, 640.
115. Y. Kohayashi, T. Fukuyama, J. Heterocycl. Chem. 1998, 35, 1043.
116. H. Josien, S.-B. Ko, D. Bom, D. P. Curran, Chem. Eur. J. 1998, 4, 67.
117. D. Hoppe, Angew. Chem. 1974, 86, 878; Angew. Chem. Int. Ed. Engl. 1974, 13, 789.
118. D. Hoppe, Angew. Chem. 1974, 86, 878; Angew. Chem. Int. Ed. Engl. 1974, 13, 789.
119. A. J. M. van Beijnen, Macromolecules 1983, 16, 1679.
120. D. Hoppe, U. Schöllkopf, Liebigs Ann. Chem. 1972, 763, 1.
121. A. M. van Leusen, Synthesis 1991, 531.
122. A. M. van Leusen, H. Siderius, B. E. Hoogenboom, D. van Leusen, Tetrahedron Lett. 1972, 13, 5337.
123. A. M. van Leusen, J. Wildeman, O. H. Oldenziel, J. Org. Chem. 1977, 42, 1153.
124. R. Schröder, U. Schöllkopf, E. Blume, I. Hoppe. Ann. 1975, 533.
125. U. Schöllkopf, P. H. Porsch, E. Blume, Ann. 1976, 7122.
126. a) M. Sawamura, Y. Ito, T. Hayashi, Tetrahedron Lett. 1989, 30, 2247;
127. b) Y. Ito, M. Sawamura, H. Hamashima, T. Hayashi, Tetrahedron Lett. 1989, 30, 4681;
128. c) S. D. Pastor, R. Kesselring, A. Togni, J. Organomet. Chem. 1992, 429, 415.
129. S. Marcaccini, T. Torroba, Org. Prep. Proced. Int. 1993, 25, 141.
130. a) I. Ugi, R. Meyr, Chem. Ber. 1961, 94, 2229;
131. b) I. Hagedorn, U. Eholzer, Chem. Ber. 1965, 98, 936.
132. I. Ugi, R. Meyr, Angew. Chem. 1962, 74, 9; Angew. Chem. Int. Ed. Engl. 1962, 1, 8.
133. I. Ugi, R. Meyr, Angew. Chem. 1962, 74, 9; Angew. Chem. Int. Ed. Engl. 1962, 1, 8.
134. H. Bock, I. Ugi, J. Prakt. Chem. 1997, 339, 385.
135. a) When partly fluorinated parent compounds are used in the P-3CR, the products often are liquid and highly volatile: A. Dömling, J. Achatz, unpublished results;
136. b) K. Burger, K. Mütze, W. Hollweck, B. Koksch, Tetrahedron 1998, 54, 5915.
137. R. H. Baker, A. H. Schlesinger, J. Am. Chem Soc. 1945, 67, 1499.
138. E. Müller, B. Zech, Liebigs Ann. Chem. 1966, 696, 72.
139. G. L. Grunewald, W. J. Brouillette, J. A. Finney, Tetrahedron Lett. 1980, 21, 1219.
140. B. Zech, E. Müller, Liebigs Ann. Chem. 1968, 715, 47.
141. a) U. Fetzer, I. Ugi, Justus Liebigs Ann. Chem. 1962, 659, 184;
142. b) J. Rachon, Chimica 1983, 37, 299.
143. a) M. Passerini, Gazz. Chim. Ital. 1924, 54, 529;
144. b) E. Müller, B. Zech, Justus Liebigs Ann. Chem. 1966, 696, 72;
145. c) B. Zech, E. Müller, Justus Liebigs Ann. Chem. 1968, 715, 47.
146. J. W. McFarland, J. Org. Chem. 1963, 28, 2179.
147. a) M. Passerini, Gazz. Chim. Ital. 1922, 52, 432;
148. b) M. Passerini, Gazzz. Chim. Ital. 1926, 56, 826;
149. c) N. Kreuzkamp, K. Lämmerhirt, Angew. Chem. 1968, 80, 2179; Angew. Chem. Int. Ed. Engl. 1968, 7, 372.
150. c) N. Kreuzkamp, K. Lämmerhirt, Angew. Chem. 1968, 80, 2179; Angew. Chem. Int. Ed. Engl. 1968, 7, 372.
151. R. Neidlein, Z. Naturforsch. B 1964. 19, 1159.
152. T. El Gomati, J. Firl, I. Ugi, Chem. Ber. 1977. 110, 1603.
153. R. Neidlein, Arch. Pharm. 1966, 299, 603.
154. W. C. Lumma, J. Org. Chem. 1981, 46, 3668.
155. S. W. Kim, S. M. Bauer, R. W. Armstrong, Tetrahedron Lett. 1998, 39, 7031.
156. T. Ziegler, R. Schlömer, C. Koch, Tetrahedron Lett. 1998, 39, 5057.
157. S. König, R. Klösel, R. Karl, I. Ugi, Z. Naturforsch. B 1994, 49, 1586.
158. M. Passerini, G. Ragni, Gazz. Chim. Ital. 1931, 61, 826.
159. E. Oliveri-Mandala, B. Alagna, Gazz. Chim. Ital. 1910, 40, 441.
160. I. Ugi, F. K. Rosendahl, Chem. Ber. 1961, 94, 2233.
161. M. Passerini, Gazz. Chim. Ital. 1923, 53, 331.
162. S. Sebti, A. Foucaud, Synthesis 1983, 546.
163. R. Bossio, C. F. Marcos, S. Marcaccini, R. Pepino, Tetrahedron Lett. 1997, 38, 2519.
164. R. Bossio, S. Marcaccini, R. Pepino, Liebigs Ann. Chem. 1991, 1107.
165. R. Bossio, S. Marcaccini, R. Pepino, T. Torroba, Synthesis 1993, 783.
166. K. Kobayashi, T. Matoba, I. Susumu, M. Takashi, O. Morikawa, H. Konishi, Chem. Lett. 1998, 551.
167. R. Bossio, S. Marcaccini, R. Pepino, T. Torroba, J. Chem. Soc. Perkin Trans. 1 1996, 229.
168. a) I. Ugi, R. Meyr, U. Fetzer, C. Steinbrückner, Angew. Chem. 1959, 71, 386;
169. b) I. Ugi, C. Steinbrückner, Angew. Chem. 1960, 72, 267.
170. I. Ugi, F. K. Rosendahl, F. Bodesheim, Liebigs Ann. Chem. 1963, 666, 54.
171. N-isocyanides also react in the U-4CR, albeit with more modest yields: G. Zinner, D. Moderhack, W. Kliegel, Chem. Ber. 1969, 102, 2536.
172. R. Kaufhold, I. Ugi, Liebigs Ann. Chem. 1967, 709, 11.
173. a) O. Mumm, Ber. Dtsch. Chem. Ges. 1910, 43, 887;
174. b) O. Mumm, H. Hesse, H. Volquartz, Ber. Dtsch. Chem. Ges. 1915, 48, 379.
175. a) I. Ugi, H. Aigner, M. L. V. Arnaez, G. Glahsl, P. Lemmen, R. Stöcklein-Schneiderwind, M. Balla-Tamasi in Vorträge anlässlich der Königsteiner Chromatographie-Tage (Ed.: H. Aigner), Waters, Eschborn, 1984, p. 1;
176. b) H. Aigner, Dissertation, Technische Universität München, 1984.
177. H. Quast, S. Aldenkortt, Eur. Chem. J. 1996, 2, 462.
178. G. Neyer, J. Achatz, B. Danzer, I. Ugi, Heterocycles 1990, 30, 863.
179. A. M. L. Hoel, J. Nielsen, Tetrahedron Lett. 1999, 40, 3941.
180. I. Ugi, D. Marquarding, R. Urban in Chemistry and Biochemisty of Amino Acids, Peptides, and Proteins (Ed.: B. Weinstein), Marcel Dekker, New York, 1982, p. 246-289.
181. a) R. Urban, I. Ugi, Angew. Chem. 1975, 87, 67; Angew. Chem. Int. Ed. Engl. 1975, 14, 61;
182. a) R. Urban, I. Ugi, Angew. Chem. 1975, 87, 67; Angew. Chem. Int. Ed. Engl. 1975, 14, 61;
183. b) W. Pfrengle, H. Kunz, J. Am. Chem. Soc. 1988, 110, 651;
184. c) M. Goebel, I. Ugi, Synthesis 1991, 1095;
185. d) H. Kunz, W. Pfrengle, K. Rück, W. Sager, Synthesis 1991, 1039;
186. e) I. Ugi, M. Goebel, N. Bachmeyer, A. Demharter, C. Fleck, R. Gleixner, S. Lehnhoff, Chem. Pept. Proteins 1993, 5-6, 59-72;
187. f) S. Lehnhoff, M. Goebel, R. M. Karl, R. Klösel, I. Ugi, Angew. Chem. 1995, 107, 1208; Angew. Chem. Int. Ed. Engl. 1995, 34, 1104.
188. f) S. Lehnhoff, M. Goebel, R. M. Karl, R. Klösel, I. Ugi, Angew. Chem. 1995, 107, 1208; Angew. Chem. Int. Ed. Engl. 1995, 34, 1104.
189. H. R. Divanfard, Z. Lysenko, P. C. Wang, M. M. Joullié, Synth. Commun. 1978, 8, 269.
190. a) P. M. Hardy, I. N. Lingham, Int. J. Protein Res. 1983, 21, 406;
191. b) T. Yamada, N. Motoyama, T. Taniguchi, T. Kazuta, T. Miyazawa, S. Kuwata, K. Matsumoto, Chem. Lett. 1987, 723;
192. c) T. Yamada, Y. Nakamura, T. Miyazawa, T. Kuwata, K. Matsumoto, Jpn. Chem. Express 1993, 8, 161.
193. K. Matsumoto, T. Uchida in Organic Synthesis at High Pressure (Eds.: K. Matsumoto, R. M. Acheson), Wiley, New York, 1991, p. 164.
194. T. Yamada, Y. Omote, Y. Yamanaka, T. Miyazawa, S. Kuwata, Synthesis 1998, 991.
195. A. Failli, H. Immer, M. Götz, Can. J. Chem. 1979, 57, 3257.
196. T. A. Keating, R. W. Armstrong, J. Am. Chem. Soc. 1996, 118, 2574.
197. A. M. Strocker, T. A. Keating, P. A. Tempest, R. W. Armstrong, Tetrahedron Lett. 1996, 37, 1149.
198. A. M. M. Mjalli, S. Sarshar, T.J. Baiga, Tetrahedron Lett. 1996, 37, 2943.
199. H. Hatanaka, I. Ishimura, Tetrahedron Lett. 1983, 24, 4837.
200. a) H. P. Isenring, W. Hofheinz, Synthesis 1981, 385;
201. b) H. P. Isenring, W. Hofheinz, Tetrahedron 1983, 39, 2591.
202. J. Geller, I. Ugi, Chem. Scr. 1983, 22, 85.
203. C. F. Hoyng, A. D. Pateöl, Tetrahedron Lett. 1980, 21, 4795.
204. I. Ugi, K. Offermann, Chem. Ber. 1964, 97, 2996.
205. I. Ugi, A. Arora, H. Burghard, G. Eberle, H. Eckert, G. George, G. Gokel, H. Herlinger, E. von Hinrichs, P. Hoffmann, H. Klusacek, H. L. Lam, D. Marquarding, H. S. Nah, K. Offeremann, D. Rehn, S. Stüber, M. Tamasi, R. Urban, L. Wackerle, S. Zahr, H. v. Zychlinsky in Peptides 1974 (Ed.: Y. Wolman), Wiley, New York, 1975, p. 71.
206. M. Waki, Y. Minematsu, J. Meienhofer, N. Izumiya, Chem. Lett. 1979, 823.
207. M. Waki, J. Meienhofer, J. Am. Chem. Soc. 1977, 99, 6075.
208. T. Lindhorst, H. Bock, I. Ugi, Tetrahedron 1999, 55, 7411.
209. R. J. Linderman, S. Binet, S. R. Petrich, J. Org. Chem. 1999, 64, 336.
210. H. Gröger, M. Hatam, J. Kintscher, J. Martens, Synth. Commun. 1996, 26, 3383.
211. P. Bukall, I. Ugi, Heterocycles 1981, 15, 381.
212. K. Tsuchida, K. Ikeda, Y. Mizuno, Chem. Pharm. Bull. 1980, 28, 2748.
213. F. K. Rosendahl, I. Ugi, Liebigs Ann. Chem. 1963, 666, 65.
214. R. Huisgen, H. Gotthardt, H. O. Bayer, F. C. Schäfer, Angew. Chem., 1964, 76, 185; Angew. Chem. Int. Ed. Engl. 1964, 3, 136.
215. R. Huisgen, H. Gotthardt, H. O. Bayer, F. C. Schäfer, Angew. Chem., 1964, 76, 185; Angew. Chem. Int. Ed. Engl. 1964, 3, 136.
216. T. A. Keating, R. W. Armstrong, J. Am. Chem. Soc. 1995, 117, 7842.
217. S. W. Kim, Y. S. Shin, S. Ro, Bioorg. Med. Chem. Lett. 1998, 8, 1665.
218. A. Dömling, I. Ugi, Tetrahedron 1993, 49, 9495.
219. H. Gröger, M. Hatam, J. Martens, Tetrahedron 1995, 51, 7173.
220. J. Kintscher, J. Martens, Synthesis 1992, 837.
221. A. Dömling, Nucleotides Nucleosides 1998, 17, 1667.
222. A. Dömling, K.-Z. Chi, M. Barrere. Bioorg. Med. Chem. Lett. 1999, 9, 2871.
223. W. Maison, I. Schlemminger, O. Westerhoff, J. Martens, Bioorg. Med. Chem. Lett. 1999, 9, 581.
224. G. Gokel, G. Lüdke, I. Ugi in Isonitrile Chemistry (Ed.: I. Ugi), Academic Press, New York, 1971, p. 159.
225. R. Bossio, S. Marcaccini, P. Paoli, R. Pepino, Synthesis 1994, 672.
226. T. Ziegler, H. J. Kaisers, R. Schlömer, C. Koch, Tetrahedron 1999, 55, 8397.
227. a) O. Lockhoff, Angew. Chem. 1998, 110, 3634; Angew. Chem. Int. Ed. Engl. 1998, 37, 3436;
228. a) O. Lockhoff, Angew. Chem. 1998, 110, 3634; Angew. Chem. Int. Ed. Engl. 1998, 37, 3436;
229. b) O. Lockhoff (Bayer AG), DE-A 19636538, 1996.
230. A. Dömling, W. Richter (Morphochem AG), WO-A 98102860, 1996.
231. W. K. C. Park, M. Auer, H. Jaschke, C. H. Wong, J. Am. Chem. Soc. 1996, 118, 10150.
232. a) A. Studer, P. Jeger, P. Wipf, D. P. Curran, J. Org. Chem. 1997, 62, 2917;
233. b) A. Studer, S. Hadida, R. Ferritto, S.-Y. Kim, P. Jeger, P. Wipf, D. P. Curran, Science 1997, 275, 823.
234. A. J. Polyakov, N. N. Aseeva, V. G. Bezrukova, Izv. Akad. Nauk SSSK Ser. Khim. 1974, 7, 1597.
235. D. P. Sutherlin, T. M. Stark, R. Hughes, R. W. Armstrong, J. Org. Chem. 1996, 61, 8350.
236. D. Obrecht, C. Abrecht, A. Grieder, J. M. Villalgordo, Helv. Chim. Acta 1997, 80, 65.
237. X. Cao, E. J. Moran, D. Siev, A. Lio, C. Ohashi, A. M. M. Mjalli, Bioorg. Med. Chem. Lett. 1995, 5, 2953.
238. E. J. Moran, S. Shashar, J. F. Cargill, M. M. Shahbaz, A. Lio, A. M. M. Mjalli, R. W. Armstrong, J. Am. Chem. Soc. 1995, 117, 10787.
239. Z. Li, S. L. Yeo, C. J. Pallen, A. Ganesan, Bioorg. Med. Chem. Lett. 1998, 8, 2443.
240. S. W. Kim, S. M. Bauer, R. W. Armstrong, Tetrahedron Lett. 1998, 39, 6993.
241. a) C. D. Floyd, M. Whittaker (British Biotech), WO-A 96/26918, 1996;
242. b) C. D. Floyd, L. A. Hamett, A. Miller, S. Patel, L. Saroglou, M. Whittaker, Synlett 1998, 637;
243. c) S. Patel, L. Saroglou, C. D. Floyd, A. Miller, M. Whittaker, Tetrahedron Lett. 1998, 39, 8333.
244. R. H. Schlessinger, G. R. Bebernitz, P. Lin, H. Poss, J. Am. Chem. Soc. 1985, 107, 1777.
245. G. Opitz, W. Merz, Justus Liebigs Ann. Chem., 1962, 652, 163.
246. a) I. Ugi, F. Bodesheim, Liebigs Ann. Chem. 1963, 666, 61;
247. b) G. Zinner, W. Kliegel, Arch. Pharm. 1966, 299, 746;
248. c) G. Zinner, W. Bock, Arch. Pharm. 1973, 306, 94.
249. A. Failli, V. Nelson, H. Immer, M. Götz, Can. J. Chem. 1973, 51, 2769.
250. T. Yamada, Y. Nakamura, T. Miyazawa, S. Kuwata, K. Matsumoto, Chem. Express, 1993, 8, 161.
251. 2+ in matrix metalloproteases (MMP); MMP inhibitors are interesting in the fields of tumor angiogenesis, restenosis, rheumatoid arthritis, neurodegenerative disease, and healing of wounds, among other things.
252. a) D. Moderhack, Liebigs Ann. Chem. 1973, 359;
253. b) G. Zinner, D. Moderhack, O. Hantelmann, W. Bock, Chem. Ber. 1974, 107, 2947;
254. c) G. Zinner, D. Moderhack, W. Heuer, Z. Chem. 1975, 15, 55;
255. d) G. Zinner, O. Hantelmann, Arch. Pharm. 1975, 308, 321;
256. e) D. Moderhack, M. Lorke, Chem. Ztg. 1979, 103, 268.
257. I. Ugi, E. Böttner, Liebigs Ann. Chem. 1963, 670, 74.
258. S. Zychlinski, I. Ugi, Heterocycles 1998, 49, 29.
259. N. Kreutzkamp, K. Lämmerhirt, Angew. Chem. 1968, 80, 394; Angew. Chem. Int. Ed. Engl. 1968, 7, 372.
260. N. Kreutzkamp, K. Lämmerhirt, Angew. Chem. 1968, 80, 394; Angew. Chem. Int. Ed. Engl. 1968, 7, 372.
261. D. S. Matteson, Bailey, Chem. Ind. 1967, 191.
262. E. Haslinger, Monatsh. Chem. 1978, 109, 747.
263. H. Groß, J. Gloede, I. Keitel, D. Kunath, J. Prakt. Chem. 1968, 37, 192.
264. T. A. Keating, R. W. Armstrong, J. Org. Chem. 1998, 63, 867.
265. L. Weber, Drug Disc. Today 1998, 3, 378.
266. L. Weber, S. Waltbaum, C. Broger, K. Gubernator, Angew. Chem. 1995, 107, 2452; Angew. Chem. Int. Ed. Engl. 1995, 34, 2280.
267. L. Weber, S. Waltbaum, C. Broger, K. Gubernator, Angew. Chem. 1995, 107, 2452; Angew. Chem. Int. Ed. Engl. 1995, 34, 2280.
268. K. M. Short, B. W. Ching, A. M. M. Mjalli, Tetrahedron Lett. 1996, 37, 7489.
269. a) G. Opitz, A. Griesinger, H. W. Schubert, Justus Lieb. Ann. Chem. 1963, 665, 91;
270. b) G. Opitz, W. Merz, Justus Lieb. Ann. Chem. 1963, 652, 158;
271. c) R. Neidlein, Arch. Pharm. 1965, 298, 491;
272. d) R. Neidlein, Arch. Pharm. 1964, 297, 589;
273. e) R. Neidlein, Angew. Chem. 1964, 76, 440, Angew. Chem. Int. Ed. Engl. 1964, 3, 382.
274. e) R. Neidlein, Angew. Chem. 1964, 76, 440, Angew. Chem. Int. Ed. Engl. 1964, 3, 382.
275. H. Bienaymé, K. Bouzid, Tetrahedron Lett. 1998, 39, 2735.
276. K. M. Short, B. W. Ching, A. M. M. Mjalli, Tetrahedron 1997, 53, 6653.
277. G. Gokel, G. Lüdke, I. Ugi in Isonitrile Chemistry (Ed.: I. Ugi), Academic Press, New York, 1971, p. 158.
278. A. Demharter, Dissertation, Technische Universität München. 1995.
279. A. Demharter, W. Hörl, E. Herdtweck, I. Ugi, Angew. Chem. 1996, 108, 185; Angew. Chem. Int. Ed. Engl. 1996, 35, 173.
280. A. Demharter, W. Hörl, E. Herdtweck, I. Ugi, Angew. Chem. 1996, 108, 185; Angew. Chem. Int. Ed. Engl. 1996, 35, 173.
281. I. Ugi, A. Demharter, A. Hörl, T. Schmid, Tetrahedron 1996, 52, 11657.
282. S. J. Park, G. Keum, S. B. Kang, H. Y. Hoh, Y. Kim, Tetrahedron Lett. 1998, 39, 7109.
283. A. Dömling, W. Richter, I. Ugi, Nucleotides Nucleosides 1997, 16, 1753.
284. I. Ugi, A. Dömling, B. Gruber, M. Heilingbrunner, C. Heiß, W. Hörl in Software-Entwicklung in der Chemie (Ed.: R. Moll), GDCh, Frankfurt, 1995, p. 113.
285. I. Ugi, M. Goebel, B. Gruber, H. Heilingbrunner, C. Heiß, H. Hörl, O. Kern, M. Starnecker, A. Dömling, Res. Chem. Intermed. 1996, 22, 625.
286. T. Yamada, N. Motoyama, T. Taniguchi, Y. Kazuta, T. Miyazawa, S. Kuwata, K. Matsumoto, M. Sugiura, Chem. Lett. 1987, 723.
287. B. M. Ebert, I. Ugi, M. Grosche, E. Herdtweck, W. A. Herrmann, Tetrahedron 1998, 54, 11887.
288. I. A. Natchev, Tetrahedron 1988, 44, 1511.
289. I. Ugi, W. Hörl, C. Hanusch, T. Schmid, E. Herdtweck, Heterocycles 1998, 47, 985.
290. I. Ugi, T. Schmid, J. Prakt. Chem. 1997, 339, 652.
291. I. Ugi, R Obrecht, S. Tourré, Heterocycles 1984, 21, 271.
292. I. Ugi, Angew. Chem. 1982, 94, 826; Angew. Chem. Int. Ed. Engl. 1982, 21, 810.
293. I. Ugi, Angew. Chem. 1982, 94, 826; Angew. Chem. Int. Ed. Engl. 1982, 21, 810.
294. a) I. Ugi, E. Wischhöfer, Chem. Ber. 1961, 95, 136;
295. b) M. Hatanaka, H. Yamamoto, H. Nitta, T. Ishimaru, Tetrahedron, Lett. 1981, 22, 3883;
296. c) A. Schutz, I. Ugi, J. Chem. Res. (S) 1978, 157; 2064;
297. d) K. Sjöberg, habilitation thesis, Stockholm University, 1970.
298. H. Martin, R. Herrmann, I. Ugi, Z. Naturforsch. B 1987, 42, 1588.
299. G. Neyer, I. Ugi, Synthesis 1991, 743.
300. A. Schutz, I. Ugi, H.-J. Kabbe, Z. Naturforsch. B 1979, 34, 1303.
301. H. Nitta, M. Hatanaka, T. Ishimura, J. Chem. Soc. Chem. Commun. 1987, 51.
302. K. Kehagia, I. Ugi, Tetrahedron 1995, 51, 9523.
303. A. Dömling, M. Starnecker, I. Ugi, Angew. Chem. 1995, 107, 2465; Angew. Chem. Int. Ed. Engl. 1995, 34, 2238.
304. A. Dömling, M. Starnecker, I. Ugi, Angew. Chem. 1995, 107, 2465; Angew. Chem. Int. Ed. Engl. 1995, 34, 2238.
305. A. Dömling, K. Kehagia, I. Ugi, Tetrahedron 1995, 51, 9523.
306. J. Pitlik, C. A. Townsend, Bioorg. Med. Chem. Lett. 1997, 7, 3129.
307. C. Yoakim, Antiviral Chem. Chemother. 1998, 9, 379.
308. T. A. Keating, R. W. Armstrong, J. Org. Chem. 1996, 61, 8935.
309. J. Szardenings, presented at the International Symposium Combinatorial Chemistry: New Developments and Applications in Drug Discovery, Schliersee, 1996.
310. A. Chucholowski, D. Heinrich, B. Mathys, C. Müller, Abstr. Pap. Am. Chem. Soc. 1997, 214, 287.
311. C. Hulme, J. Peng, G. Morton, J. M. Salvino, T. Herpin, R. Labaudiniere, Tetrahedron Lett. 1998, 39, 7227.
312. L. Grehn, K. Gunnarsson, U. Ragnarrson, Acta Chem. Scand. Ser. B. 1986, 40, 745.
313. C. Hulme, M. M. Morrissette, F. A. Volz, C. J. Burns, Tetrahedron Lett. 1998, 38, 1113.
314. C. Hulme, J. Peng, B. Louridas, P. Menard, P. Krolikowski, N. V. Kumar, Tetrahedron Lett. 1998, 39, 8047.
315. A. K. Szardenings, T. S. Burkoth, H. H. Lu, D. W. Tien, D. A. Campbell, Tetrahedron 1997, 53, 6573.
316. A. K. Szardenings, V. Antonenko, D. A. Campbell, N. DeFrancisco, S. Ida, L. Shi, N. Sharkov, N. Tien, Y. Wang, M. Navre, J. Med. Chem. 1999, 42, 1384.
317. C. Hulme, M.-P. Cherrier, Tetrahedron Lett. 1999, 40, 5245.
318. a) K. M. Short, B. W. Ching, A. M. M. Mjalli, Tetrahedron 1997, 53, 6653;
319. b) K. M. Short, A. M. M. Mjalli, Tetrahedron Lett. 1997, 38, 354.
320. G. C. B. Harriman, Tetrahedron Lett. 1997, 38, 5591.
321. J. Zhang, A. Jacobson, J. R. Rusche, W. Herlihy, J. Org. Chem. 1999, 64, 1074.
322. K. Rossen, J. Sager, L. M. DiMichele, Tetrahedron Lett. 1997, 38, 3183.
323. K. Rossen, P. J. Pye, L. M. DiMichele, R. P. Voante, P. J. Reider, Tetrahedron Lett. 1998, 39, 6823.
324. D. Askin, K. K. Eng, K. Rossen, R. M. Purick, K. M. Wells, R. P. Volante, P. J. Reider, Tetrahedron Lett. 1994, 35, 673.
325. R. Bossio, S. Marcaccini, P. Paoli, R. Pepino, C. Polo, Synthesis 1991, 999.
326. J. A. Deyrup, M. M. Vestling, W. V. Hagen, Tetrahedron 1969, 25, 1462.
327. M. Murakami, N. Hasegawa, T. Nagatomi, Y. Ito, Heterocycles 1998, 47, 85.
328. a) B. Ebert, Dissertation, Technische Universität München, 1998;
329. b) I. Ugi, B. Ebert, Chemosphere 2000, in press.
330. K. Paulvannan, Tetrahedron Lett. 1999, 40, 1851.
331. L. Weber, presented at the International Symposium Combinatorial Chemistry: New Developments and Applications in Drug Discovery, Schliersee, 1996.
332. Such heterocyclic compounds have antiviral properties, for example: A. Gueiffer, S. Mavel, M. Lhassani, A. Elhakmaoui, R. Snoeck, G. Andrei, O. Chavignon, J.-C. Teulade, M. Witvrouw, J. Balzarini, E. De Clercq, J.-P. Chapat, J. Med. Chem. 1998, 41, 5108.
333. a) K. Groebke, L. Weber, F. Mehlin, Synlett 1998, 661;
334. b) C. Blackburn, B. Guan, K. Shiosaki, S. Tsai, Tetrahedron Lett. 1998, 39, 3635;
335. c) C. Blackburn, Tetrahedron Lett. 1998, 39, 5469;
336. d) C. Blackburn, Tetrahedron Lett. 1998, 39, 5469;
337. e) H. Bienaymé, K. Bouzid, Angew. Chem. 1998, 110, 2349; Angew. Chem. Int. Ed. 1998, 39, 2234.
338. e) H. Bienaymé, K. Bouzid, Angew. Chem. 1998, 110, 2349; Angew. Chem. Int. Ed. 1998, 39, 2234.
339. C. Hanusch, I. Ugi, AKKIVOC 2000, in press.
340. K. Ley, R. Nast, Angew. Chem. 1965, 77, 544; Angew. Chem. Int. Ed. Engl. 1965, 4, 519.
341. K. Ley, R. Nast, Angew. Chem. 1965, 77, 544; Angew. Chem. Int. Ed. Engl. 1965, 4, 519.
342. R. Bossio, R. Marcaccini, R. Pepino, Liebigs Ann. Chem. 1993, 1229.
343. R. Bossio, S. Marcaccini, P. Paoli, P. Papaleo, R. Pepino, C. Polo, Liebigs Ann. Chem. 1991, 843.
344. R. Bossio, S. Marcaccini, S. Papaleo, R. Pepino, J. Heterocycl. Chem. 1994, 31, 397.
345. R. Bossio, C. F. Marcos, S. Marcaccini, R. Pepino, Synthesis 1997, 1389.
346. R. Bossio, C. F. Marcos, S. Marcaccini, R. Pepino, Heterocycles 1997, 45, 1589.
347. C. Zhang, E. J. Moran, T. F. Woiwode, K. M. Short, A. M. M. Mjalli, Tetrahedron Lett. 1996, 37, 751.
348. A. M. M. Mjalli, C. Zhang (Ontogen Corp.), US-A 5840721, 1997.
349. I. J. McAlpine, R. W. Armstrong. J. Org. Chem. 1996, 61, 5674.
350. A. D. Piscopio, J. F. Miller, K. Koch. Tetrahedron 1999, 55, 8189.
351. I. Ugi, W. Betz, K. Offermann, Chem. Ber. 1964, 97, 3008.
352. R. Bossio, S. Marcaccini, R. Pepino, Tetrahedron Lett. 1995, 36, 2325.
353. R. Bossio, S. Marcaccini, R. Pepino, J. Org. Chem. 1996, 61, 2202.
354. J. T. Lai, J. Org. Chem. 1980, 45, 3671.
355. Primary amines afford isocyanides under the basic phase-transfer conditions (Hoffman method) and could react in a normal U-4CR.
356. J. R. Falck, S. Manna, Tetrahedron Lett. 1981, 22, 619.
357. M. Nagi, K. Ogawa, Y. Muraoka, H. Naganawa, T. Aoyagi, T. Takeuchi, J. Antibiot. 1991, 44, 956.
358. U. Schmidt, S. Weinbrenner, J. Chem. Soc. Chem. Commun. 1994, 1003.
359. M. M. Bowers, P. Carroli, M. M. Joullié, J. Chem. Soc. Perkin Trans. 1 1989, 857.
360. T. Fukujama, B. D. Robins, A. Sachleben, Tetrahedron Lett. 1981, 22, 4155.
361. S. E. de Laszlo, P. G. Williard, J. Am. Chem. Soc. 1985, 107, 199.
362. K. Tsuchida, Y. Mizuno, K. Ikeda, Heterocycles 1981, 15, 883.
363. J. C. Boehm, D. Kingsbury, J. Org. Chem. 1986, 51, 2307.
364. K. Tsuchida, Y. Mizuno, K. Ikeda, Nucleic Acid Res. 1980, s49.
365. H. Immer, V. Nelson, W. Robinson, M. Götz, Liebigs Ann. Chem. 1973, 1789.
366. J. E. Semple, P. C. Wang, Z. Lysenko, M. M. Joullié, J. Am. Chem. Soc. 1980, 102, 7505.
367. S. M. Bauer, R. W. Armstrong, J. Am. Chem. Soc. 1999, 121, 6355.
368. D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565.
369. a) A. Dömling, I. Ugi, Angew. Chem. 1993, 105, 634; Angew. Chem. Int. Ed. Engl. 1993, 32, 563;
370. a) A. Dömling, I. Ugi, Angew. Chem. 1993, 105, 634; Angew. Chem. Int. Ed. Engl. 1993, 32, 563;
371. b) A. Dömling, I. Ugi, E. Herdtweck, Acta Chem. Scand. 1998, 52, 107.
372. Semantics of the union concept: ∩ means "combined with", ≡ means "results in the combined reaction"; for example: A-4CR ∩ U-5CR ≡ AU-7CR: the union of the Asinger four-component reaction with the Ugi five-component reaction results in the Asinger-Ugi seven-component reaction.
373. I. Ugi, W. Hörl, B. Ebert, unpublished results.
374. A. Dömling, K.-C. Chi, unpublished results.
375. L. Weber, K. Illgen, M. Almstetter, Synlett 1999, 366.
376. S. Heck, A. Dömling, Synlett 2000, 424.
377. O. Lack, L. Weber, Chimia 1996, 50, 445.
378. S. P. Raillard, G. Ji, A. D. Mann, T. A. Baer, Org. Proc. Res. Develop. 1999, 3, 177-183.
379. M. Bergemann, R. Neidlein, Helv. Chim. Acta 1999, 909, 909-918.
380. L. Williams, Third International Electronic Conference on Synthetic Organic Chemistry (ECSOC-3), 1999; http://reprints.net/ecsoc-3/ b001/b0001.htm.
381. P. Dumestre, L. El Kaim, A. Gregoire, Chem. Commun. 1999, 775-776.
382. J. S. Mason, J. Morize, P. R. Menard, D. L. Cheney, C. Hulme, R. F. Labaudiniere, J. Med. Chem. 1999, 42, 3251-3264.
383. V. Atlan, C. Buron, L. El Kaim, Synlett 2000, 4, 489-490.
384. J. Sisko, A. J. Kassick, M. Mellinger, J. J. Filan, A. Allen, M. A. Olsen, J. Org. Chem. 2000, 65, 1516.
385. C. Hulme, L. Ma, M. P., Cherrier, J. J. Romano, G. Morton, C., Duquenne, J. Salvino, R. Labaudiniere, Tetrahedron Lett. 2000, 41, 1883-1887.
386. K. Oertel, G. Zech, H. Kunz, Angew. Chem. 2000, 112, 1489-1491; Angew. Chem. Int. Ed. 2000, 39, 1431-1433.
387. K. Oertel, G. Zech, H. Kunz, Angew. Chem. 2000, 112, 1489-1491; Angew. Chem. Int. Ed. 2000, 39, 1431-1433.
388. C. Hulme, L. Ma, J. J. Romano, G. Morton, S.-Y. Tang, M. P., Cherrier, S. Choi, J. Salvino, R. Labaudiniere, Tetrahedron Lett. 2000, 41, 1889-1893.
389. C. Blackburn, B. Guan, Tetrahedron Lett. 2000, 41, 1495-1500.
390. D. Lee, J. K. Sello, S. L. Schreiber, Org. Lett. 2000, 2, 709-712.
391. S. L. Schreiber, Science 2000, 287, 1964-1969.
392. R. Leardini, D. Nanni, G. Zanardi, J. Org. Chem. 2000, 65, 2763-2772.
393. G. R. Bebernitz, T. D. Aicher, J. L. Stanton, J. Gao, S. S. Shetty, D. C. Knorr, R. J. Strohschein, J. Tan, L. J. Brand, C. Liu, W. H. Wang, C. C. Vinluan, E. L. Kaplan, C. J. Dragland, D. DelGrande, A. Islam, R. J. Lozito, X. Liu, W. M. Maniara, W. R. Mann, J. Med. Chem. 2000, 43, 2048-2257.
394. L. Weber, Curr. Opin. Chem. Biol. 2000, 4, 295-302.
395. A. Dömling, Curr. Opin. Chem. Biol. 2000, 4, 318-323.
396. K. Illgen, T. Enderle, C. Broger, L. Weber, Chem. Biol. 2000, 7, 433-441.
397. A. Chucholowski, M. Nettekoven, Chim. Oggi 2000, 50-53.