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对通过Bischler-Napieralski反应制备的那可丁及其衍生物的立体选择性进行了研究.以N-β-(3-甲氧基-4,5-亚甲二氧基苯基)乙基-6’,7’-二甲氧基苯并呋喃酮-3-酰胺(1)和N-β-(3,4-亚甲二氧基苯基)乙基-6’,7’-二甲氧基苯并呋喃酮-3-酰胺(2)为原料,经Bischler-Napieralski反应和硼氢化钠还原制得五对苯酞类四氢异喹啉类化合物对映体3,4a,4b,5a,5b,其中3和5a经氮甲基化反应得到外消旋的那可丁(α-narcotine)和白毛莨碱(β-hydrastine).该法制得的苯酞类四氢异喹啉类化合物具有一定的立体选择性,产物构型以赤式对映体为主,中间产物二氢异喹啉环8位取代基的空间位阻将导致硼氢化钠还原时产生立体选择性.
The stereoselectivity of nocodine and its derivatives prepared by the Bischler-Napieralski reaction was studied.N-β- (3-methoxy-4,5-methylenedioxyphenyl) ethyl- 6 ’, 7’-dimethoxybenzofuranone-3-amide (1) and N-β- (3,4-methylenedioxyphenyl) ethyl-6’, 7’- Benzofuranone-3-carboxamide (2) as starting materials, five pairs of phthalides tetrahydroisoquinolines enantiomers were obtained via Bischler-Napieralski reaction and sodium borohydride reduction. 3,4a, 4b, 5a , 5b, in which 3 and 5a were obtained by the methylation reaction of racemic butyl (α-narcotine) and the white-scale (β-hydrastine). The method of phthalides tetrahydroisoquinolines The stereoselectivity of the product is stereoselective. The stereochemistry of the product is erythro enantiomer. The steric hindrance of the 8-substituent of the dihydroisoquinoline ring in the intermediate product will lead to the stereoselectivity of sodium borohydride reduction.