Novel syntheses of enantiopure hexahydroimidazo[1,5-b]isoquinolines and tetrahydroimidazo[1,5-b]isoquinolin-1(5H)-ones via iminium cation cyclizations |
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| Authors: | Katritzky Alan R Suzuki Kazuyuki He Hai-Ying |
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| Institution: | Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu |
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| Abstract: | Condensations of chiral diamines 11a-c with benzotriazole and formaldehyde gave benzotriazolyl intermediates 12a-c; similar condensations of alpha-amino-amides 10a-c with benzotriazole and paraformaldehyde gave 14a-c. Subsequent treatment of 12a-c and 14a-c with AlCl(3) led to enantiopure tricyclic 1,2,3,5,10,10a-hexahydroimidazo1,5-b]isoquinolines 1a-c and 2,3,10,10a-tetrahydroimidazo1,5-b]isoquinolin-1(5H)-ones 15a-c, respectively, via Lewis acid promoted iminium cation cyclizations. |
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