Acceleration of the Passerini reaction in the presence of nucleophilic additives / Mironov M.A., Ivantsova M.N., Tokareva M.I., Mokrushin V.S. // Tetrahedron Letters. - 2005. - V. 46, l. 23. - P. 3957-3960.

ISSN:
00404039
Type:
Article
Abstract:
An accelerating effect of nucleophilic additives was revealed for the Passerini multi-component reaction. The influence of aqueous solutions on the reaction rate was studied in detail and the direct involvement of water in the bond-making step was attributed as the basis of an accelerating effect. Other nucleophiles were tested as alternatives to water; as a result N-hydroxysuccinimide is proposed as an accelerant of the Passerini reaction. © 2005 Elsevier Ltd. All rights reserved.
Author keywords:
Aqueous solutions; Catalysis; Isocyanides; Nucleophilic additives; Passerini reaction
Index keywords:
succinimide derivative; water; aqueous solution; article; chemical bond; chemical reaction; chemical reaction kinetics; hydrolysis; Passerini reaction; reaction time; reversed phase high performance l
DOI:
10.1016/j.tetlet.2005.04.050
Смотреть в Scopus:
https://www.scopus.com/inward/record.uri?eid=2-s2.0-18844363719&doi=10.1016%2fj.tetlet.2005.04.050&partnerID=40&md5=660ba12a5a6d1d9b16fcbba728eec8b1
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Link https://www.scopus.com/inward/record.uri?eid=2-s2.0-18844363719&doi=10.1016%2fj.tetlet.2005.04.050&partnerID=40&md5=660ba12a5a6d1d9b16fcbba728eec8b1
Affiliations Dept. Technol. of Organ. Synthesis, Urals State Technical University, 620002 Ekaterinburg, Russian Federation
Author Keywords Aqueous solutions; Catalysis; Isocyanides; Nucleophilic additives; Passerini reaction
Chemicals/CAS water, 7732-18-5
References Grieco, (1998) Organic Synthesis in Water, , Blackie Academic & Professional Glasgow; Anastas, P., Williamson, T.C., (1998) Green Chemistry, Frontiers in Benign Chemical Synthesis and Processes, , Oxford University Press New York; Rideout, D.C., Breslow, R., (1980) J. Am. Chem. Soc., 102, p. 7816; Grieco, P.A., Garner, P., Zhen-Min, He., (1983) Tetrahedron Lett., 24, p. 1897; Breslow, R., Maitra, U., Rideout, D., (1983) Tetrahedron Lett., 24, p. 1901; Blokzijl, W., Engberts, J.B.F.N., (1993) Angew. Chem., Int. Ed. Engl., 32, p. 1545; Ugi, I., Dömling, A., (2000) Angew. Chem., Int. Ed., 39, p. 3168; Pirrung, M.C., Das Sarma, K., (2004) J. Am. Chem. Soc., 126, p. 444; Pirrung, M.C., Das Sarma, K., (2004) Synlett, p. 1425; Mironov, M.A., Ivantsova, M.N., Mokrushin, V.S., (2003) Mol. Divers., 6, p. 193; Hagedorn, I., Eholzer, U., (1965) Chem. Ber., 98, p. 936; Hagedorn, I., Eholzer, U., Winkelmann, H.D., (1964) Angew. Chem., 76, p. 583; König, S., Klösel, R., Karl, R., Ugi, I., (1994) Z. Naturforsch B., 49, p. 1586; Ugi, I., Meyer, R., (1962) Angew. Chem., Int. Ed. Engl., 1, p. 8; Jenner, G., (2002) Tetrahedron Lett., 43, p. 1235; note; Anderson, G.W., Zimmerman, J.E., Gallahan, F.M., (1963) J. Am. Chem. Soc., 85, p. 3039; König, W., Geiger, R., (1970) Chem. Ber., 103, p. 788; note; Passerini, M., (1921) Gazz. Chim. Ital., 51, p. 126; Baker, R.H., Stanonis, D., (1951) J. Am. Chem. Soc., 73, p. 699; Weber, L., Illgen, K., Almstetter, M., (1999) Synlett, p. 366; Dömling, A., (2002) Curr. Opin. Chem. Biol., 6, p. 306; Mironov, M.A., Mokrushin, V.S., Maltsev, S.S., (2003) Synlett, p. 943; Kusebauch, U., Beck, B., Messer, K., Herdweck, E., Dömling, A., (2003) Org. Lett., 5, p. 4021; Frey, R., Galbraith, S.G., Guelfi, S., Lamberth, C., Zeller, M., (2003) Synlett, p. 1536; Denmark, S., Fan, Y., (2003) J. Am. Chem. Soc., 125, p. 7825
Correspondence Address Mironov, M.A.; Dept. Technol. of Organ. Synthesis, Urals State Technical University, 620002 Ekaterinburg, Russian Federation; email: mir@htf.ustu.ru
CODEN TELEA
Language of Original Document English
Abbreviated Source Title Tetrahedron Lett.
Source Scopus