Katritzky Alan R, Suzuki Kazuyuki, He Hai-Ying
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA.
J Org Chem. 2002 Nov 15;67(23):8224-9. doi: 10.1021/jo0203241.
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-hexahydroimidazo[1,5-b]isoquinolines 1a-c and 2,3,10,10a-tetrahydroimidazo[1,5-b]isoquinolin-1(5H)-ones 15a-c, respectively, via Lewis acid promoted iminium cation cyclizations.
手性二胺11a - c与苯并三唑和甲醛缩合得到苯并三唑基中间体12a - c；α-氨基酰胺10a - c与苯并三唑和多聚甲醛进行类似缩合得到14a - c。随后用AlCl₃处理12a - c和14a - c，通过路易斯酸促进的亚胺阳离子环化反应，分别得到对映体纯的三环1,2,3,5,10,10a - 六氢咪唑并[1,5 - b]异喹啉1a - c和2,3,10,10a - 四氢咪唑并[1,5 - b]异喹啉 - 1(5H)-酮15a - c。
