YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Synthesis of Phenolbetaine Derivatives : Introduction of Functional Groups to C-ring and Chemical Transformation of BC-ring of Protoberberine

페놀베타인 유도체합성 : 프로토베르베린에서 C-환의 관능기도입 및 BC-환의 화학적 변환

  • Published : 1996.12.01
Download PDF
⟨ Previous Next ⟩

Abstract

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 comp ound 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.

Keywords

References

  1. Yakhak Hoeji v.38 Synthesis of 8-methyl-8, 14-cycloberberine derivatives Hwang, S. H.;Kim, J. H.;Yim, H. Y.;Kim, S. K.
  2. Yakhak Hoeji v.39 Synthesis of protoberberine Related compounds and its activities Hwang, S. H.;Yim, H. Y.;Woo, S. J.;Kim, J. H.;Kim, S. K.
  3. Chem. Pharm. Bull. v.33 Chemical transformation of protoberberines(Ⅶ) Hanaoka, M.;Kim, S. K.;Inoue, M.;Nagami, K.;Shimada, Y.;Yasuda, S.
  4. Chem. Pharm. Bull. v.35 Chemical transformation of protoberberines(ⅩⅠ) Hanaoka, M.:Cho, M. J.;Marutoni, M.;Mukai, C.
  5. Chem. Pharm. Bull. v.40 Fluorescence properties of 2-substituted 6-7- or 8-methoxyquinoline-4-carboxylic acid Derivatives Yoshida, T.;Moriyama, Y.;Nakano, S.
  6. Chem. Pharm. Bull. v.40 Novel Disease modifying Antirhumatic Drugs, 1. Synthesis and Antiarthritic activity of 2-(4-methylphenyl) benzothiazoles Hori, N.;Tsukamoto, G.;Imaura, A.;Ohashi, M.;Saito, T.;Yoshino, K.
  7. Chem. Pharm. Bull. v.33 Reaction of 4-Aroylquinazolines with Sodium hydroxide Higashino, T.;Takemoto, M.;Hayashi, E.
  8. Heterocycles v.19 Ring Diversion of protoberberine alkaloids conversion of berberine into Non-Naturally occuring 11, 12-oxygenated protoberberines Hanaoka, M.;Inoue, M.;Takahashi, M;Yasuda, S.
  9. Yakhak Hoeji v.36 Synthesis of protoberberine derivatives and their biological activies Kim, S. K.;Kwon, C. H.;Yook, C. S.;Rho, Y. S.;Seo, S. H.;Choung, S. Y.;Chung, S. H.;Kim, D. H.;Hwang, S. H.
  10. Yakhak Hoeji v.38 Synthesis of protoberberine related compound and their Antifungal activites Kim, S. K.;Kim, D. H.;Chung, K. H.;Hwang, S. H.;Kim, J. H.
  11. Chem. Pharm. Bull. v.36 A convenient transformation of spyrobenzylisoquinolins to dehydrophthalide isoquinolines Hanaoka, M.;Mitsuoka, T.;Yasuda, S.;Kim, S. K.