Synthesis of New trans-2-Benzyl-3-(furan-2-yl)-4-substituted-1,2,3,4-tetrahydroisoquinolinones
Abstract
:Introduction
Results and Discussion
Conclusions
Experimental
General
(±)-trans- and (±)-cis-2-Benzyl-3-(furan-2-yl)-1-oxo-1,2,3,4-tetrahydro-4-isoquinoline Carboxylic Acid (trans-5 and cis-5) and By-products 6 and 7: General Procedure for Determination of the Ratios of the Products Obtained from 3 and 4 on a Small Scale Experiments
Reaction between 3 and 4 Performed on a Large Scale in Dichloroethane.
(±)-cis-2-Benzyl-3-(furan-2-yl)-1-oxo-1,2,3,4-tetrahydro-4-isoquinoline Carboxylic Acid (cis-5).
(±)-trans-2-Benzyl-3-(furan-2-yl)-1-oxo-1,2,3,4-tetrahydro-4-isoquinoline Carboxylic Acid (trans-5).
2-[2-(Benzylamino)-2-oxoethyl]benzenecarboxylic Acid (6).
4-(Furan-2-yl)methylidene-1H-isochromene-1,3-dione (7).
Reaction between 3 and 4 Performed on a Large Scale in Pyridine.
(±)-trans-Methyl-2-Benzyl-3-(furan-2-yl)-1-oxo-1,2,3,4-tetrahydro-4-isoquinoline Carboxylate (8).
(±)-trans-2-Benzyl-3-(furan-2-yl)-4-hydroxymethyl-1,2,3,4-tetrahydroisoquinolin-1-one (9).
(±)-trans-2-Benzyl-1-oxo-3-(furan-2-yl)-4-tosyloxymethyl-1,2,3,4-tetrahydroisoquinolin-1-one (10).
General Procedure for the Preparation of (±)-trans-2-Benzyl-1-oxo-3-(furan-2-yl)-4-(N,N-disubstitutedaminomethyl)-1,2,3,4-tetrahydroisoquinolin-1-ones (11a-g).
(±)-trans-2-Benzyl-1-oxo-3-(furan-2-yl)-4-[(piperidin-1-yl)methyl)]-1,2,3,4-tetrahydroisoquinolin-1-one (11a).
(±)-trans-2-Benzyl-1-oxo-3-(furan-2-yl)-4-[(4-phenyl-piperazin-1-yl)methyl)]-1,2,3,4-tetrahydroisoquinolin-1-one (11b).
(±)-trans-2-Benzyl-1-oxo-3-(furan-2-yl)-4-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl)methyl)]-1,2,3,4-tetrahydroisoquinolin-1-one (11c).
(±)-trans-2-Benzyl-1-oxo-3-(furan-2-yl)-4-[4-(3-chlorophenyl)-piperazin-1-yl)methyl)]-1,2,3,4-tetrahydroisoquinolin-1-one (11d).
(±)-trans-2-Benzyl-1-oxo-3-(furan-2-yl)-4-[4-fluorophenylpiperazin-1-yl)methyl)]-1,2,3,4-tetrahydroisoquinolin-1-one (11e).
(±)-trans-2-Benzyl-1-oxo-3-(furan-2-yl)-4-[4-(morpholin-4-yl)methyl]-1,2,3,4-tetrahydroisoquinolin-1-one (11f).
(±)-trans-2-Benzyl-1-oxo-3-(furan-2-yl)-4-[4-(thiomorpholin-4-yl)methyl]-1,2,3,4-tetrahydroisoquinolin-1-one (11g).
(±)-trans-2-Benzyl-3-(furan-2-yl)-4-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline (12).
Acknowledgements
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Kandinska, M.I.; Kozekov, I.D.; Palamareva, M.D. Synthesis of New trans-2-Benzyl-3-(furan-2-yl)-4-substituted-1,2,3,4-tetrahydroisoquinolinones. Molecules 2006, 11, 403-414. https://doi.org/10.3390/11060403
Kandinska MI, Kozekov ID, Palamareva MD. Synthesis of New trans-2-Benzyl-3-(furan-2-yl)-4-substituted-1,2,3,4-tetrahydroisoquinolinones. Molecules. 2006; 11(6):403-414. https://doi.org/10.3390/11060403
Chicago/Turabian StyleKandinska, Meglena I., Ivan D. Kozekov, and Mariana D. Palamareva. 2006. "Synthesis of New trans-2-Benzyl-3-(furan-2-yl)-4-substituted-1,2,3,4-tetrahydroisoquinolinones" Molecules 11, no. 6: 403-414. https://doi.org/10.3390/11060403