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Article info. : 2006; 3(2) (pp 173~179)


Preparation, Reactivity and Tautomeric Preferences of Novel (1H-Quinolin-2-ylidene)propan-2-ones

H. Loghmani-Khouzania,*, B. Osmailowskib, R. Gawineckib, E. Kolehmainenc, R.W. Harringtond and W. Cleggd

aDepartment of Chemistry, Faculty of Sciences, University of Isfahan 81746-73441 IR Iran
bDepartment of Chemistry, Technical and Agricultural University, Seminaryjna 3PL-85-326 Bydgoszcz, Poland
cDepartment of Chemistry, P.O. Box 35, FIN-40014, University of Jyväskylä, Finland
dSchool of Natural Sciences (Chemistry), University of Newcastle, Newcastle upon Tyne NE1 7RU, U.K

(Received1 January 2006 , Accepted 15 March 2006)

      1,1-Difluoro-3-(1H-quinolin-2-ylidene)propan-2-one 1a, 1,1,1-trifluoro-3-(1H-quinolin-2-ylidene)propan-2-one 1b, 1,1,1-trifluoro-3-(4-chloro-1H-quinolin-2-ylidene)propan-2-one 1c and 1,3-dibromo-1,1-difluoro-3-(2-quinolyl)propan-2-one 2 are prepared and characterized by various spectroscopic techniques. The crystal structure of 1a is determined by X-ray diffraction. Furthermore, a series of previously known non-halogenated (1H-quinolin-2-ylidene)propan-2-ones 1d-1h are oxidized with AgBrO3 in the presence of AlCl3. In all cases, 2-(1-bromo-1-chloromethyl)quinoline 3 is obtained in high yield. The bromination order and sites of 1a are analyzed based on ab initio MP2 and DFT calculations for the molecule and its anions.

Keywords: 2-Ketomethylquinolines, Enaminones, Oxidation, Crystallography, GIAO calculations

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