PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Czasopismo
2013 | 11 | 4 | 569-583
Tytuł artykułu

P-Triazinylphosphonium chlorides as a new group of coupling reagents

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Tertiary phosphines in reaction with 2-chloro-4,6-dialkoxy-1,3,5-triazines gave unstable quaternary P-triazinylphosphonium chlorides, which readily decomposed with a departure of the alkyl group of the triazine ring substituent. Stable quaternary P-triazinylphosphonium chlorides were obtained only in reaction of 2-chloro-4,6-diphenoxy-1,3,5-triazine. Both, stable quaternary P-triazinylphosphonium chlorides as well unstable analogues prepared in situ activated carboxylic acid yielding “superactive” triazine esters, useful as highly efficient reagents in peptide bond synthesis. [...]
Wydawca
Czasopismo
Rocznik
Tom
11
Numer
4
Strony
569-583
Opis fizyczny
Daty
wydano
2013-04-01
online
2013-01-23
Twórcy
  • Institute of General and Environmental Chemistry, Lodz University of Technology, 90-924, Lodz, Poland
  • Institute of Organic Chemistry, Lodz University of Technology, 90-924, Lodz, Poland
  • Institute of Organic Chemistry, Lodz University of Technology, 90-924, Lodz, Poland
Bibliografia
  • [1] A. El-Faham, F. Albericio, Chem. Rev. 111, 6557 (2011) http://dx.doi.org/10.1021/cr100048w[Crossref]
  • [2] C. A.G.N. Montalbetti, V. Falque, Tetrahedron 61, 10827 (2005) http://dx.doi.org/10.1016/j.tet.2005.08.031[Crossref]
  • [3] S. -Y. Han, Y.-A. Kim, Tetrahedron 60, 2447 (2004) http://dx.doi.org/10.1016/j.tet.2004.01.020[Crossref]
  • [4] F. Albericio, R. Chinchilla, D.J. Dodsworth, C. Nájera, Org. Prep. Proced. Int. 33, 203 (2001) http://dx.doi.org/10.1080/00304940109356592[Crossref]
  • [5] P. Li, J.C. Xu, J. Pept. Res. 58, 129 (2001) http://dx.doi.org/10.1034/j.1399-3011.2001.00867.x[Crossref]
  • [6] D. T. Elmore, Amino Acids, Peptides, Proteins 33, 83 (2002)
  • [7] L. A. Carpino, M. Beyermann, H. Wenschuh, M. Bienert, Acc. Chem. Res. 29, 268 (1996) http://dx.doi.org/10.1021/ar950023w[Crossref]
  • [8] J. M. Humphrey, A.R. Chamberlin, Chem. Rev. 97, 2243 (1997) http://dx.doi.org/10.1021/cr950005s[Crossref]
  • [9] P. D. Bailey, An introduction to peptide chemistry (Wiley, Chichester, 1990)
  • [10] M. Bodanszky, Principles of peptide synthesis (Springer, Berlin, 1984) http://dx.doi.org/10.1007/978-3-642-96763-4[Crossref]
  • [11] V. J. Hruby, R. Schwyzer, Peptide chemistry, design and synthesis of peptides, conformational analysis and biological functions (Pergamon, Oxford, 1998) and references cited therein
  • [12] Z. J. Kamiński, J. Prakt. Chem. 332, 579 (1990) http://dx.doi.org/10.1002/prac.19903320426[Crossref]
  • [13] B. Kolesinska, Cent. Eur. J. Chem. 8, 1147 (2010) http://dx.doi.org/10.2478/s11532-010-0114-z[Crossref]
  • [14] D. B.G. Williams, M. Lawton, J. Org. Chem. 75, 8351 (2010) http://dx.doi.org/10.1021/jo101589h[Crossref]
  • [15] B. Kolesinska, R. Motylski, Z.J. Kaminski, M. Kwinkowski, W. Kaca, Acta Poloniae Pharm. Drug Res. 68, 387 (2011)
  • [16] J. Hradil, V. Chvalovsky, Collect. Czech. Chem. Commun. 33, 2029 (1968) [Crossref]
  • [17] P. S. Radhakrishnamurti, G.P. Panigrahi, J. Indian Chem. Soc. 46, 318 (1969)
  • [18] J. F. Manning, J. P. Mason, J. Am. Chem. Soc. 62, 3136 (1940) http://dx.doi.org/10.1021/ja01868a065[Crossref]
  • [19] B. C. Lee, J.H. Yoon, C.G. Lee, I. Lee, J. Phys. Org. Chem. 7, 273 (1994) http://dx.doi.org/10.1002/poc.610070602[Crossref]
  • [20] F. R. Allen, O. Kennard, Chem Des. Autom. News 8, 131 (1993)
  • [21] R. Preussmann, H. Schneider, F. Epple, Arzneim. Forsch. 19, 1059 (1969)
  • [22] Z. J. Kaminski, Int. J. Pept. Prot. Res. 43, 312 (1994) http://dx.doi.org/10.1111/j.1399-3011.1994.tb00396.x[Crossref]
  • [23] A. Olczak, M.M. Błaszczyk, M.L. Główka, B. Kolesińska, Z.J. Kamiński, Polish J. Chem. 82, 1413 (2008)
  • [24] B. Kolesinska, Z.J. Kamiński, Polish J. Chem. 82, 2115 (2008)
  • [25] B. Kolesińska, Z. J. Kamiński, Tetrahedron 65, 3573 (2009) http://dx.doi.org/10.1016/j.tet.2009.03.017[Crossref]
  • [26] T. M. Krygowski, J. Chem. Inf. Comput. Sci. 33, 70 (1993) http://dx.doi.org/10.1021/ci00011a011[Crossref]
  • [27] F. H. Allen, Acta Cryst. B58, 380 (2002)
  • [28] Z. J. Kamiński, P. Paneth, J. Rudziński, J. Org. Chem. 63, 4248 (1998) http://dx.doi.org/10.1021/jo972020y[Crossref]
  • [29] Z. J. Kamiński, B. Kolesińska, J. Kolesińska, G. Sabatino, M. Chelli, P. Rovero, M. Błaszczyk, M.L. Główka, A.M. Papini, J. Am. Chem. Soc. 127, 16912 (2005) http://dx.doi.org/10.1021/ja054260y[Crossref]
  • [30] B. Kolesińska, J. Frączyk, A.M. Papini, Z.J. Kamiński, Chemistry Today (Chimica Oggi) 25, 26 (2007)
  • [31] Z. J. Kamiński, Pol. J. Chem. 65, 2077 (1991)
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-012-0190-3
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.