Abstract
New organic reactions allow chemical transformations which were previously not possible. Therefore, new reactions are important contributions to the progress in the field of organic synthesis.In this series we describe the design, scope, and limitations of newly-discovered multi-component reactions (MCRs). Herein, a first example of a MCR is introduced which allows general access to the class of 2,4-di- and 2,4,5-trisubstituted thiazoles.
Similar content being viewed by others
References
Kolbe, H., Ann., 54 (1845) 253.
Barton, D. H. R., Aldrichimica Acta, 23 (1990) 3.
Seebach, D., Angew. Chem., 102 (1990) 1363-1409.
Knowles, W. S., Angew. Chem. Int. Ed. Engl., 41 (2002) 1998
Nojori, R., Angew. Chem. Int. Ed. Engl., 41 (2002) 2008
Sharpless, K. B., Angew. Chem. Int. Ed. Engl., 41 (2002) 2024.
Wender, P. A., Handy, S. T. and Wright, D. L., Chemistry Industry, (1997) 765.
Deslongchamps, P., Aldrichimica Acta, 17 (1984) 59-71.
Dömling, A., Herdtweck, E. and Ugi, I., Acta Chem. Scand., 52 (1998) 107.
Hulme, C. and Gore, V., Curr. Med. Chem., 10 (2003) 51.
Bienaymé, H., Hulme, C., Oddon, G. and Schmitt, P., Chem. Eur. J., 6 (2000) 3321.
Dömling, A. and Ugi, I., Angew. Chem. Int. Ed. Engl., 39 (2000) 3168.
Beck, B., Dömling, A. and Hess, S., Bioorg. Med. Chem. Lett., 10 (2000) 1701-1705.
Boger, D. and Cai, H., Angew. Chem. Int. Ed. Engl., 38 (1999) 448.
Kazlauskas, R., Lidgard, R. O., Wells, R. J. and Vetter, W., Tetrahedron Lett., 28 (1977) 3183.
Höfle, G., Bedorf, N., Steinmetz, H., Schomburg, D., Gerth, K. and Reichenbach, H., Angew. Chem. Int. Ed. Engl., 35 (1996) 1567.
Sone, H., Kigoshi, H. and Yamada, K., Tetrahedron, 53 (1997) 8149.
Ojika, M., Suzuki, Y., Tsukamoto, A., Sakagami, Y., Fudou, R., Yoshimura, T. and Yamanaka, S., J. Antibiot., 51 (1998) 275.
Bycroft, B. W. and Gowland, M. S., J. Chem. Soc., Chem. Commun., (1978) 256.
Lawton, L. A., Morris, L. A. and Jaspars, M., J. Org. Chem., 64 (1999) 5329.
Rashid, M. A., Gustafson, K. R., Boswell, J. L. and Boyd, M. R., J. Nat. Prod., 63 (2000) 956.
Ugi, I., Meyr, R., Fetzer, U. and Steinbrückner, C., Angew. Chem., 71 (1959) 386.
Chupp, J. P. and Leschinsky, K. L., J. Org. Chem., 40 (1975) 66.
Keating, T. A. and Armstrong, R. W., J. Org. Chem., 63 (1998) 867.
Heck, S. and Dömling, A., Synlett, (2000) 424.
Hantzsch, A., Ann. Chem., 249 (1888) 1.
Libersch, J., in Houben Weyl-Methoden der Organischen Chemie, Springer-Verlag, New York, 1994, E8b, 1.
Schöllkopf, U., Porsch, P.-H. and Lau, H.-H., Liebigs Ann. Chem., (1979) 95.
Numani, K., Yamada, M., Fukui, T. and Matsumoto, K., J. Org. Chem., 59 (1994) 7635.
Henkel, B., Sax, M. and Dömling, A., Tetrahedron Lett., 44 (2003) 3679.
McKervey, A. M., O'Sullivan, M. B., Myers, P. L. and Green, R. H., J. Chem. Soc., Chem. Commun., (1993) 94.
Foeldi, A., Acta Chim. Acad. Sci. Hung, 3 (1953) 501.
Teichel, P. M. and Knebel, W. J., Inorg. Chem., 11 (1972) 1285
Herdeis, C. and Beck, W., Chem. Ber., 116 (1983) 3205
Kantlehner, W., Wagner, F. and Bredereck, H., Liebigs Ann. Chem., (1980) 344
Bossio, R., Marcaccini, S., Pepino, P. and Paoli, P., J. Heterocycl. Chem., 31 (1994) 729
Pawlik, J. W., Kebede, N., Bird, N. P., Day, A. C. and Barltrop, J. A., J. Org. Chem., 60 (1995) 8138
Bienaymé, H., Tetrahedron Lett., 24 (1998) 4255.
Yamada, M., Fukui, T. and Numani, K., Tetrahedron Lett., 36 (1995) 257.
Schöllkopf, U., Porsch, P. H. and Lau, H. H., Liebigs Ann. Chem., (1979) 1444.
Almstetter, M. and Dömling, A., unpublished.
Dömling A., Curr. Op. Chem. Biol., 4 (2000) 318
Dömling A., Curr. Op. Chem. Biol., 6 (2002) 303.
http://www.daylight.com/dayhtml/doc/theory/theory.html/.
Kolb, J., Beck, B. and Dömling, A., Tetrahedron Lett., 43 (2002) 6897.
Sir Jack Baldwin, personal communication, MCR2003, Genua, 14-16-04-2003.
L. Straver, CAD4 Operating System, Version 5.0, B.V. ENRAF-NONIUS, Delft, The Netherlands (1989).
C. K. Fair, Molen: An Interactive Intelligent System for Crystal Structure Analysis, ENRAF-NONIUS, Delft, The Netherlands (1990). Data Collection Software for Nonius Kappa-CCD Devices, Delft, The Netherlands, 2001.
Otwinowski, Z. and Minor, W., 'Processing of X-ray Diffraction Data Collected in Oscillation Mode', W. C. Carter Jr. and R. M. Sweet (eds), Methods in Enzymology, 276 (1996) 307, Academic Press, New York, U.S.A., 1996.
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. and Camalli M., SIR92, J. Appl. Cryst., 27 (1994) 435-436.
Sheldrick, G. M., SHELXL-97, University of Göttingen, Göttingen, Germany, 1998.
International Tables for Crystallography, Vol. C, Tables 6.1.1.4 (pp. 500-502), 4.2.6.8 (pp. 219-222) and 4.2.4.2 (pp. 193-199), in A. J. C. Wilson (ed.), Kluwer Academic Publishers, Dordrecht, The Netherlands, 1992.
Spek, A. L., PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands, 2001.
CCDC 211340 (1a), 211339 (2), 211338 (19), 211342 (29), 211341 (49), 211337 (50) contains the supplementary crystallographic data (excluding structure factors) for the structures reported in this paper. These data can be obtained, free of charge, via www.ccdc.cam.ac.uk/conts/retreiving.html (or from the CCDC, 12 Union Road, Cambridge, CB2 1EZ, U.K.); fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kolb, J., Beck, B., Almstetter, M. et al. New MCRs: The first 4-component reaction leading to 2,4-disubstituted thiazoles. Mol Divers 6, 297–313 (2003). https://doi.org/10.1023/B:MODI.0000006827.35029.e4
Issue Date:
DOI: https://doi.org/10.1023/B:MODI.0000006827.35029.e4