基于各种拆分方法的四氢异喹啉生物碱、手性亚磺酰胺和顺式哌虫啶的合成研究
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摘要
本文研究了半量拆分、循环拆分、自发结晶等各种高效拆分技术,并将它们运用到四氢异喹啉生物碱及其衍生物、手性亚磺酰胺和顺式哌虫啶的合成中,开展了下列三方面的工作：
(1)以1-苯乙胺的拆分为模型反应,对半量拆分和全量拆分进行了详细的比较研究,发现半量拆分优于全量拆分。以高藜芦胺为原料,经过酰化反应、Bischler-Napieralski反应和亚胺的还原反应高收率地得到四个消旋的1-取代四氢异喹啉化合物(RS)-(±)-Ⅱ-4a-4d.然后,通过半量拆分技术分别以45%、40%、41%和38%的收率得到(S)-(-)-norcryptostyline Ⅰ[(S)-(-)-Ⅱ-4a]、(S)-(-)-norcryptostyline Ⅱ[(S)-(-)-Ⅱ-4b]、(R)-(+)-salsolidine[(R)-(+)-Ⅱ-4c]和(S)-(-)-norlaudanosine[(S)-(-)-Ⅱ-4d],并且使用手性溶剂化试剂(CAS,chiral solvating agents)通过1H NMR方法测定其光学纯度。对母液中不需要的异构体的碱催化消旋和氧化还原消旋进行了深入的研究,我们发现通过“一锅法”氧化还原消旋化可分别以98%、98%、97%和95%的收率得到消旋体1-取代四氢异喹啉(RS)-(±)-Ⅱ-4a-4d。同样地,我们利用半量拆分技术以38%的收率得到索非那新药物重要中间体(S)-Ⅱ-25,并利用同样的“一锅”氧化还原消旋化方法将不需要的异构体以98%的收率消旋化,所得的消旋体可再进一步拆分,这样的“拆分-消旋”过程可循环多次,称为“循环拆分”。
(2)我们以四种亚磺酸钠Ⅲ-1a-1d为原料,先将其转化为酰氯,再与(R)-N-苄基-1-苯乙胺反应得到一对非对映异构体亚磺酰胺混合物Ⅲ-3a-3d,然后运用自发结晶技术在正己烷和乙酸乙酯(hexane/EtOAc=9:1)混合溶剂中分别以28%、29%、27%和31%的收率得到单一异构体(R,Ss)-Ⅲ-3a-3d,接着分别高收率地将它们转化为手性亚磺酸甲酯(RS)-Ⅲ-5,再转化为手性亚磺酰胺(Ss)-Ⅲ-6。这是一个新颖的、简便的制备光学纯的(SS)-苯亚磺酰胺(Ss)-Ⅲ-6a、(Ss)-对甲苯亚磺酰胺(Ss)-Ⅲ-6b、(Ss)-对氯苯亚磺酰胺(Ss)-Ⅲ-6c、(SS)-对氟苯亚磺酰胺(Ss)-Ⅲ-6d的方法。另外,在此研究过程中,我们还发现了一种运用水合肼在DMSO中还原亚磺酸酯和亚磺酰胺制备对称二芳基二硫醚的简便方法。
(3)我们发展了一种顺式哌虫啶的高效合成方法。首先,使用三乙胺催化Michael加成稠环反应,将哌虫啶中间体Ⅳ-5的收率从67%大大提高到92%。对醚化反应采用氯化亚砜催化,几乎定量地得到哌虫啶的顺反立体异构体混合物Ⅳ-6,根据顺反异构体的溶解度不同,在正丙醇和水(n-PrOH:H2O=1:2)的混合溶剂中活性高的一对顺式异构体结晶析出,母液中活性较低的一对反式异构体通过酸催化差向异构化为等量的顺反立体异构体混合物。另外,我们还合成了一系列的哌虫啶类似物Ⅳ-15,并测试了其杀虫活性,结果发现其中Ⅳ-15d、Ⅳ-15f和Ⅳ-15m不但对刺吸式口器害虫褐飞虱具有较高活性,而且对同翅目蚜科害虫苜蓿蚜也表现出高活性。
This dissertation describes the study on some efficient resolution methods, such as half-equivalent resolution, recycling resolution and spontaneous crystallization. Syntheses of tetrahydroisoquinoline alkaloids, chiral arylsulfinamides and cis-IPP based on these efficient resolution methods are also discussed. The paper contains three parts as described below:
Part one:A comparative study on resolution of1-phenylethylamine as a model reaction with half equivalent or one equivalent resolving agent was performed, and the results revealed that half-equivalent resolution is superior to the equal-equivalent. Then four racemic1-substituted1,2,3,4-tetrahydroisoquinolines (THIQs)(RS)-(±)-Ⅱ-4a-4d were efficiently prepared from homoveratrylamine in excellent yields by N-carboxylation, Bischler-Napieralski reaction and reduction of imines. Chiral resolution of these THIQs (RS)-(±)-Ⅱ-4a-4d with half equivalent of resolving agents smoothly afforded the desired enantiomerically pure (S)-(-)-norcryptostyline Ⅰ [(S)-(-)-Ⅱ-4a],(S)-(-)-norcryptostyline Ⅱ [(S)-(-)-Ⅱ-4b],(R)-(+)-salsolidine [(R)-(+)-Ⅱ-4c] and (S)-(-)-norlaudanosine [(S)-(-)-Ⅱ-4d] in45%,40%,41%and38%yields, respectively. The enantiomeric purities of the above obtained THIQs were determined by1H NMR method with CSAs. Base-catalyzed and redox methods were used for racemization of the undesired enantiomerically enriched THIQs,(R)-(+)-Ⅱ-4a,(R)-(+)-Ⅱ-4b,(S)-(-)-Ⅱ-4c and (R)-(+)-Ⅱ-4d, from the mother liquors, and the result indicated that undesired THIQs could be efficiently racemized via a one-pot redox protocol to afford the corresponding racemic THIQs (RS)-(±)-Ⅱ-4a-4d in98%,98%,97%and95%yields, respectively. Moreover,(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (S)-Ⅱ-25, an important intermediate of solifenacin, was efficiently synthesized in38%yield by a half-equivalent resolution. The undesired (R)-II-25was efficiently racemized via the same method in98%yield. The obtained racemic Ⅱ-25could be used for further resolution. This "resolution-racemization" process could be conducted repetitively.
Part two:Sodium arylsulfinates Ⅲ-1a-1d were converted into arysulfinyl chlorides, which were then treated with (R)-N-benzyl-l-phenylethanamine to afford diastereomeric mixtures of N-benzyl-N-(1-phenylethyl)-arylsulfinamides Ⅲ-3a-3d. By using a mixture of hexane and ethyl acetate (hexane/EtOAc=9:1) as the solvent, diastereomerically pure (R,Ss)-N-benzyl-N-(1-phenylethyl)-arylsulfinamides (R,Ss)-Ⅲ-3a-3d spontaneously crystallized in28%,29%,27%and31%yields, respectively. The diastereomerically pure compounds (R,Ss)-Ⅲ-3were then converted into four enantiopure (Rs)-methyl arylsulfinates (Rs)-Ⅲ-5, and finally into four enantiopure (Ss)-arylsulfinamides (Ss)-Ⅲ-6in good yields. Thus, a novel and simple process for the preparation of enantiomerically pure (Ss)-benzenesulfinamide (Ss)-Ⅲ-6a,(Ss)-p-toluenesulfinamide (Ss)-Ⅲ-6b,(Ss)-p-chlorobenzenesulfinamide (Ss)-Ⅲ-6c and (Ss)-p-fluorobenzenesulfinamide (Ss)-Ⅲ-6d has been developed. In addition, synthesis of diaryl disulfides via mild reduction of arylsulfinates and arylsulfinamides with hydrazine monohydrate in DMSO was achieved.
Part three:A new process for the preparation of cis-IPP was developed. Using triethylamine as catalyst in a Michael addition, the yield of an intermediate compound Ⅳ-5was greatly increased from67%to92%. Mixture of cis and trans-IPP Ⅳ-6was obtained quantitatively via a thionyl chloride catalyzed etherification. The cis-IPP was readily precipitated from a mixed solvent of n-propanol and water (n-PrOH/H2O=1:2), which was based on the different of the solubility of the cis and trans diastereoisomers. The less active trans-IPP in the mother liquor could be epimerized into an equal-equivalent mixture of cis and trans-IPP under acidic conditions. In addition, a series of N-alkyl1-((6-chloropyridin-3-yl)methyl)-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridi n-5-amines Ⅳ-15were synthesized, and insecticidal activities of these compounds were evaluated. Compounds Ⅳ-15d, Ⅳ-15f and Ⅳ-15m showed high insecticidal activities against both sucking pest Nilaparvata lugens and lepidopteran Aphis medicaginis.
(1)以1-苯乙胺的拆分为模型反应,对半量拆分和全量拆分进行了详细的比较研究,发现半量拆分优于全量拆分。以高藜芦胺为原料,经过酰化反应、Bischler-Napieralski反应和亚胺的还原反应高收率地得到四个消旋的1-取代四氢异喹啉化合物(RS)-(±)-Ⅱ-4a-4d.然后,通过半量拆分技术分别以45%、40%、41%和38%的收率得到(S)-(-)-norcryptostyline Ⅰ[(S)-(-)-Ⅱ-4a]、(S)-(-)-norcryptostyline Ⅱ[(S)-(-)-Ⅱ-4b]、(R)-(+)-salsolidine[(R)-(+)-Ⅱ-4c]和(S)-(-)-norlaudanosine[(S)-(-)-Ⅱ-4d],并且使用手性溶剂化试剂(CAS,chiral solvating agents)通过1H NMR方法测定其光学纯度。对母液中不需要的异构体的碱催化消旋和氧化还原消旋进行了深入的研究,我们发现通过“一锅法”氧化还原消旋化可分别以98%、98%、97%和95%的收率得到消旋体1-取代四氢异喹啉(RS)-(±)-Ⅱ-4a-4d。同样地,我们利用半量拆分技术以38%的收率得到索非那新药物重要中间体(S)-Ⅱ-25,并利用同样的“一锅”氧化还原消旋化方法将不需要的异构体以98%的收率消旋化,所得的消旋体可再进一步拆分,这样的“拆分-消旋”过程可循环多次,称为“循环拆分”。
(2)我们以四种亚磺酸钠Ⅲ-1a-1d为原料,先将其转化为酰氯,再与(R)-N-苄基-1-苯乙胺反应得到一对非对映异构体亚磺酰胺混合物Ⅲ-3a-3d,然后运用自发结晶技术在正己烷和乙酸乙酯(hexane/EtOAc=9:1)混合溶剂中分别以28%、29%、27%和31%的收率得到单一异构体(R,Ss)-Ⅲ-3a-3d,接着分别高收率地将它们转化为手性亚磺酸甲酯(RS)-Ⅲ-5,再转化为手性亚磺酰胺(Ss)-Ⅲ-6。这是一个新颖的、简便的制备光学纯的(SS)-苯亚磺酰胺(Ss)-Ⅲ-6a、(Ss)-对甲苯亚磺酰胺(Ss)-Ⅲ-6b、(Ss)-对氯苯亚磺酰胺(Ss)-Ⅲ-6c、(SS)-对氟苯亚磺酰胺(Ss)-Ⅲ-6d的方法。另外,在此研究过程中,我们还发现了一种运用水合肼在DMSO中还原亚磺酸酯和亚磺酰胺制备对称二芳基二硫醚的简便方法。
(3)我们发展了一种顺式哌虫啶的高效合成方法。首先,使用三乙胺催化Michael加成稠环反应,将哌虫啶中间体Ⅳ-5的收率从67%大大提高到92%。对醚化反应采用氯化亚砜催化,几乎定量地得到哌虫啶的顺反立体异构体混合物Ⅳ-6,根据顺反异构体的溶解度不同,在正丙醇和水(n-PrOH:H2O=1:2)的混合溶剂中活性高的一对顺式异构体结晶析出,母液中活性较低的一对反式异构体通过酸催化差向异构化为等量的顺反立体异构体混合物。另外,我们还合成了一系列的哌虫啶类似物Ⅳ-15,并测试了其杀虫活性,结果发现其中Ⅳ-15d、Ⅳ-15f和Ⅳ-15m不但对刺吸式口器害虫褐飞虱具有较高活性,而且对同翅目蚜科害虫苜蓿蚜也表现出高活性。
This dissertation describes the study on some efficient resolution methods, such as half-equivalent resolution, recycling resolution and spontaneous crystallization. Syntheses of tetrahydroisoquinoline alkaloids, chiral arylsulfinamides and cis-IPP based on these efficient resolution methods are also discussed. The paper contains three parts as described below:
Part one:A comparative study on resolution of1-phenylethylamine as a model reaction with half equivalent or one equivalent resolving agent was performed, and the results revealed that half-equivalent resolution is superior to the equal-equivalent. Then four racemic1-substituted1,2,3,4-tetrahydroisoquinolines (THIQs)(RS)-(±)-Ⅱ-4a-4d were efficiently prepared from homoveratrylamine in excellent yields by N-carboxylation, Bischler-Napieralski reaction and reduction of imines. Chiral resolution of these THIQs (RS)-(±)-Ⅱ-4a-4d with half equivalent of resolving agents smoothly afforded the desired enantiomerically pure (S)-(-)-norcryptostyline Ⅰ [(S)-(-)-Ⅱ-4a],(S)-(-)-norcryptostyline Ⅱ [(S)-(-)-Ⅱ-4b],(R)-(+)-salsolidine [(R)-(+)-Ⅱ-4c] and (S)-(-)-norlaudanosine [(S)-(-)-Ⅱ-4d] in45%,40%,41%and38%yields, respectively. The enantiomeric purities of the above obtained THIQs were determined by1H NMR method with CSAs. Base-catalyzed and redox methods were used for racemization of the undesired enantiomerically enriched THIQs,(R)-(+)-Ⅱ-4a,(R)-(+)-Ⅱ-4b,(S)-(-)-Ⅱ-4c and (R)-(+)-Ⅱ-4d, from the mother liquors, and the result indicated that undesired THIQs could be efficiently racemized via a one-pot redox protocol to afford the corresponding racemic THIQs (RS)-(±)-Ⅱ-4a-4d in98%,98%,97%and95%yields, respectively. Moreover,(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (S)-Ⅱ-25, an important intermediate of solifenacin, was efficiently synthesized in38%yield by a half-equivalent resolution. The undesired (R)-II-25was efficiently racemized via the same method in98%yield. The obtained racemic Ⅱ-25could be used for further resolution. This "resolution-racemization" process could be conducted repetitively.
Part two:Sodium arylsulfinates Ⅲ-1a-1d were converted into arysulfinyl chlorides, which were then treated with (R)-N-benzyl-l-phenylethanamine to afford diastereomeric mixtures of N-benzyl-N-(1-phenylethyl)-arylsulfinamides Ⅲ-3a-3d. By using a mixture of hexane and ethyl acetate (hexane/EtOAc=9:1) as the solvent, diastereomerically pure (R,Ss)-N-benzyl-N-(1-phenylethyl)-arylsulfinamides (R,Ss)-Ⅲ-3a-3d spontaneously crystallized in28%,29%,27%and31%yields, respectively. The diastereomerically pure compounds (R,Ss)-Ⅲ-3were then converted into four enantiopure (Rs)-methyl arylsulfinates (Rs)-Ⅲ-5, and finally into four enantiopure (Ss)-arylsulfinamides (Ss)-Ⅲ-6in good yields. Thus, a novel and simple process for the preparation of enantiomerically pure (Ss)-benzenesulfinamide (Ss)-Ⅲ-6a,(Ss)-p-toluenesulfinamide (Ss)-Ⅲ-6b,(Ss)-p-chlorobenzenesulfinamide (Ss)-Ⅲ-6c and (Ss)-p-fluorobenzenesulfinamide (Ss)-Ⅲ-6d has been developed. In addition, synthesis of diaryl disulfides via mild reduction of arylsulfinates and arylsulfinamides with hydrazine monohydrate in DMSO was achieved.
Part three:A new process for the preparation of cis-IPP was developed. Using triethylamine as catalyst in a Michael addition, the yield of an intermediate compound Ⅳ-5was greatly increased from67%to92%. Mixture of cis and trans-IPP Ⅳ-6was obtained quantitatively via a thionyl chloride catalyzed etherification. The cis-IPP was readily precipitated from a mixed solvent of n-propanol and water (n-PrOH/H2O=1:2), which was based on the different of the solubility of the cis and trans diastereoisomers. The less active trans-IPP in the mother liquor could be epimerized into an equal-equivalent mixture of cis and trans-IPP under acidic conditions. In addition, a series of N-alkyl1-((6-chloropyridin-3-yl)methyl)-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridi n-5-amines Ⅳ-15were synthesized, and insecticidal activities of these compounds were evaluated. Compounds Ⅳ-15d, Ⅳ-15f and Ⅳ-15m showed high insecticidal activities against both sucking pest Nilaparvata lugens and lepidopteran Aphis medicaginis.
引文
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