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

Kudelko A., Zieliński W.

Polish Journal of Applied Chemistry

2008

Vol. 52, nr 3-4

123-130

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.

Isoquinoline Syntheses via delta2-Oxazolines. Part VIII. Cyclization of 2-Acetamido-1,2-diphnylethan-1-ol Derivatives into Isoquinoline Systems

Kopczyński T.

Polish Journal of Chemistry

2001

Vol. 75, nr 9

1317-1325

(Received December 28th, 2000; revised manuscript April 25th, 2001) The results of the conversion of 2-acetamido-1,2-diphenylethan-1-ol derivatives (1) into 1-methyl-4-phenylisoquinoline derivatives (2) have been described. The mechanism proposed for these reaction assumes the existence of protonated 2-oxazolines (3), carbonium ions (4), and unsaturated amides (5 and 6) as intermediates.

Structure of N2-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]-(1R,1S)-6,7-dimethoxy-1-(3-pyridylmethyl)-1,2,3,4-tetrahydro-2-isoquinolinecarboxo amide

Maurin J., Czarnocki Z., Paluchowska B.

Polish Journal of Chemistry

1999

vol. 73 nr 2

377-383

N2-[2-Chlorophenyl)-1,3-thiazol-2-yl]-(1R,1S)-6,7-dimethoxy-1-(3-pyridylmethyl)-1,2,3,4-tetrahydro-2-isoquinolinecarboxo amide (C27H25CIN4O3S) combines the aminothiazole fragment with the isoquinoline segment of known pharmacological activity. Confirmation of a substituent at N2 of isoquinoline is determined by attractive Coulombic interaction between carbonyl oxygen and thiazole sulphur atom.