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페놀베타인 유도체합성: 프로토베르베린에서 C-환의 관능기도입 및 BC-환의 화학적 변환
우성주(Seong Ju Woo),황순호(Soon Ho Hwang),박예진(Yea Jin Park),홍유화(You Hwa Hong),이마세(Ma Se Lee),김인종(In Jong Kim),김신규(Sin Kyu Kim) 대한약학회 1996 약학회지 Vol.40 No.6
Betaine was treated with hydrochloric acid and then with sodium borohydride to give a hydroxy compound 2. The reaction of 2 with thionyl chloride followed by thiourea led a compound 5. Oxidation of compound 2 with pyridinium dichromate(PDC) and succesive treatment with Lawesson''s reagent also afforded the same compound 5. Cleavage of N-C14 bond compound of 7 was carried out via two reaction sequence from the compound 4. Finally, compound 10 was sythesized by a series of transformations from the compound 4.
우성주,박예진,황순호,홍유화,김남재,김인종,김신규 慶熙大學校 1996 論文集 Vol.25 No.-
Tetrahydroberberine-13-one was treated with ethylchloroformate to give the C_8-N bond cleaved product 1. On the treatment with Lawesson's reagent (LAS), chloroketone 2 derived from the hydrolysis of 1 afforded the thioketone 3. On the other hand, spirotype-chloroketone 4 was transformed to diaziridine 8 by a reduction, chlorination and aziridine introduction. Also, spirotype-chlorothioketone 6 was obtained from chloroketone 4.
황순호,임형업,우성주,김신규 慶熙大學校 1994 論文集 Vol.23 No.-
We have synthesized protoberberine derivatives from tetra- hydroberberinium perchlorate. On quaternization of a several protoberberine derivativese with methyl iodide, the formation of the cis methiodides the corresponding trans methiodides increased according to the order of the bulkiness of the 14-substituent as H>CH₃>CN. The N-methyl signal of the cis 14-substituted quinolisidine methiodides was conformed to appear at higher field than those of the corresponding trans methiodides except for the 14-cyano methiodides in their NMR specta.