An Highly Efficient Synthesis of Nitriles and Application to the Synthesis of Capsaicinoids

• Main Authors: Lin, Gow-Juin, 林國鈞
• Other Authors: Eng-Chi Wang
• Format: Others
• Language: zh-TW
• Published: 1998
• Online Access: http://ndltd.ncl.edu.tw/handle/74471327520996435227

碩士 === 高雄醫學院 === 藥學研究所 === 86 === In this thesis, the aryl and alkyl and alkyl aldehydes were readily convertedto corresponding nitriles in good yields using hydroxylamine and phthalic anhydride as reagents in one pot. Based on this method, a practical strategy for the synthesis of capsaicinoids was accoplished. The synthetic sequences were as follows:1).Protecting vanillin with benzyl group, 2). Converting the formly group of protectingvanillin into nitrile in one pot, 3).Transferring the nitrile function into amineto give protected vanillyl amine, 4).coupling this amine with corresponding acylchlorides, to give O-benzyloxycapsaicinoids, and finally, 5).Debenzylation withPd(OH)2/C to afford corresponding capsaicinoids. Meanwhile a standard mixture of theses capsaicinoids in ethanol was analyzedby GC-MS,giving a baseline separation. Each separated capsaicinoids was detectedand identified by EI-Mass. Furthermore these capsaicinoids were linked with a nonsteroidal antiinfammatorydrug, ibuprofen by ester bond as potential prodrugs.