Reactions of aryl phenylacetates with nitriles in the presence of trifluoromethanesulfonic anhydride

• Autorzy: Kudelko A. , Zieliński W.
• Języki publikacji: EN

Abstrakty

EN

A group of l-(2(4)-hydroxyphenyO-2-phenyl-l-ethanones has been synthesized by the reactions of an intramolecular Fnc-.s-rearrangement of the substituted aryl phenylacetates in the presence of equimolar amount of triflic anhydride. Simultaneously, in the case of esters strongly activated at the aryloxy part, isoquinolines were also obtained. The structures of products were confirmed by means of spectroscopic methods. Their pKa dissociation constants were also determined and analyzed on the basis of acid-base interactions.

Słowa kluczowe

EN

acidity; ketone; rerrangement; triflic anhydride; isoquinoline

• Wydawca: Centrum Materiałów Polimerowych i Węglowych PAN
• Czasopismo: Polish Journal of Applied Chemistry
• Rocznik: 2008
• Tom: Vol. 52, nr 3-4
• Strony: 123--130
• Opis fizyczny: Bibliogr. 17 poz.

Twórcy

autor

Kudelko A.

autor

Zieliński W.

• Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, ul. Krzywoustego 4, 44-101 Gliwice, Poland,

Bibliografia

• [1]H. NEUVONEN, K. NEUVONEN, A. Kocu, E. KLIENPETER, P. PASANEN, J. Org. Chem., 67, 6995 (2002).
• [2]I.L. BARAZNENOK, V.G. NENAJDENKO, E.S. BALENKOWA, Tetrahedron, 56,3077 (2000).
• [3]A.G. MARTINEZ, H.A. FERNANDEZ, M.F. JIMENEZ, A.G. FRAII.E , L.R. SUBRAMANIAN, M. HANACK, J. Org. Chem., 57, 1627 (1992).
• [4]A.G. MARTINEZ, H.A. FERNANDEZ, M.D. VILCHES, L.L. GUTIERREZ, L.R. SUBRAMANIAN, Synku, 1993, 229.
• [5]A.B. CHARETTE, P. CIIUA, J. Org. Chem., 63, 908 (1998).
• [6]E.W. THOMAS, Synthesis, 1993, 767.
• [7]A. KUDELKO, Z. KARCZMARZYK, A. FRUZIŃSKI, Anal. Sci., 23(8), 153 (2007).
• [8]A. ALBERT, E.P. SERJEANT, lonization Constants of Acids ami Bases, Methuen&Co Ltd, New York, p 69 (1962).
• [9]J. SHORTER, Correlation Analysis in Organic Chemistry: an Introduction to Linear Free-Energy Relationships, Clarendon Press, Oxford, chapter 3 (1973).
• [10]A. SPASSOW, Chem. Ber., 75, 779 (1942).
• [11]R. MARTIN, N. GROS, V. BoiIMER, H. K.AMMERER, Monatsh. Chem., Ill ,81 (1980).
• [12]K. W. ROSENMUND, W. SCHNUR, Justus Liebigs Ann. Chem., 460, 89 (1928).
• [13]S. SKRAUP, O. BINDER, Chem. Ber., 62, 1135 (1929).
• [14]M.F. GROSTIC, D. LEDNICER, J.Org. Chem., 32, 3251 (1967).
• [15]B. UNTERHALT, M. FAHRJG, Sci. Pharm., 64, 679 (1996).
• [16]K. KlNDLER, H. OELSCHLAGER, Arch. Pharm. (Weinheim GerJ, 287, 210 (1954).
• [17]Y.W. KIM, J.C. HACKETT, R.W. BRUEGGEMEIER, J. Med. Chem.. 47,4032 (2002).