Kandinska Meglena I, Kozekov Ivan D, Palamareva Mariana D
Department of Chemistry, University of Sofia, 1 James Bouchier Avenue, Sofia 1164, Bulgaria.
Molecules. 2006 Jun 12;11(6):403-14. doi: 10.3390/11060403.
The reaction of homophthalic anhydride and N-(furan-2-yl-methylidene)- benzylamine in different solvents and varying temperatures was studied in detail. Mixtures of the expected trans- and cis-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acids trans-5 and cis-5, along with by-products 6 and 7 were obtained in dichloroethane or benzene. In pyridine, used for the first time, the reaction became completely diastereoselective, giving only the trans isomer. The carboxylic acid group of trans-5 was transformed in four steps into cyclic aminomethyl groups which yielded various new tetrahydroisoquinolinones trans- 11a-g, incorporating both a known fragment of pharmacological interest and various pharmacophoric substituents.
详细研究了均苯四甲酸酐与N-(呋喃-2-基亚甲基)-苄胺在不同溶剂和不同温度下的反应。在二氯乙烷或苯中得到了预期的反式和顺式-1,2,3,4-四氢异喹啉-4-羧酸反式-5和顺式-5的混合物,以及副产物6和7。首次使用吡啶时,反应完全具有非对映选择性,仅生成反式异构体。反式-5的羧酸基团通过四步转化为环状氨甲基,得到了各种新的四氢异喹啉酮反式-11a-g,其既包含一个已知的具有药理学意义的片段,又包含各种药效基团取代基。