β-Carbolin-Alkaloide, II Tributyl(1-ethoxyvinyl)stannan als C2-Baustein für die Synthese von β-Carbolin-Alkaloiden
作者： Franz Bracher , Dirk Hildebrand
DOI: 10.1002/JLAC.1993199301132
关键词:
摘要: β-Carboline Alkaloids, II. – Tributyl(1-ethoxyvinyl)stannane as a C2-Building Block in the Syntheses of Alkaloids 1-Acetyl-β-carboline (4) is prepared by palladium-catalyzed coupling 1-chloro-β-carboline (1) with tributyl(1-ethoxyvinyl)stannane (3) and subsequent hydrolysis aqueous acid. Reduction 4 NaBH4 gives alkaloid 5. Nitramarine (7) annomontine (9) are from one-pot conversions acetyl group to quinoline or an aminopyrimidine ring, respectively.
sci-hub.se 参考文章(9)
Balawant S. Joshi, Venkatesh N. Kamat, Dilip H. Gawad, Some b-Carboline Alkaloids of Ailanthus malabarica DC Heterocycles. ,vol. 7, pp. 193- ,(1977) , 10.3987/S-1977-01-0193
B Proksa, D Uhrin, M Šurdíková, J Fuska, 1‐acetyl‐β‐carboline, a new metabolite of streptomyces kasugaensis Acta Biotechnologica. ,vol. 10, pp. 337- 340 ,(1990) , 10.1002/ABIO.370100405
Masanori Kosugi, Takashi Sumiya, Yukimasa Obara, Motohiro Suzuki, Hiroshi Sano, Toshihiko Migita, (α-Ethoxyvinyl)tributyltin; An Efficient Reagent for the Nucleophilic Acetylation of Organic Halides via Palladium Catalysis Bulletin of the Chemical Society of Japan. ,vol. 60, pp. 767- 768 ,(1987) , 10.1246/BCSJ.60.767
Theodor Severin, Karl-Heinz Bräutigam, Untersuchungen zurMaillard-Reaktion, VII. Bildung von β-Carbolin-Derivaten bei der Umsetzung von Tryptamin mit Xylose und Glucose Chemische Berichte. ,vol. 106, pp. 2943- 2949 ,(1973) , 10.1002/CBER.19731060924
Gregory B. Bennett, Robert B. Mason, Lee J. Alden, James B. Roach, Synthesis and antiinflammatory activity of trisubstituted pyrimidines and triazines. Journal of Medicinal Chemistry. ,vol. 21, pp. 623- 628 ,(1978) , 10.1021/JM00205A006
M. Cain, O. Campos, F. Guzman, J. M. Cook, Selenium dioxide oxidations in the indole area. Synthesis of β-carboline alkaloids Journal of the American Chemical Society. ,vol. 105, pp. 907- 913 ,(1983) , 10.1021/JA00342A045
Adrian J. Blackman, David J. Matthews, Christian K. Narkowicz, β-Carboline alkaloids from the marine bryozoan Costaticella hastata Journal of Natural Products. ,vol. 50, pp. 494- 496 ,(1987) , 10.1021/NP50051A026
Hsien-Jun Tien, Sakutaro Hirokawa, Yoshinobu Yokomori, Kiyotane Sekido, Tian-Shung Wu, The Crystal and Molecular Structure of 1-(2-Amino-4-pyrimidinyl)-β-carboline Bulletin of the Chemical Society of Japan. ,vol. 55, pp. 2236- 2238 ,(1982) , 10.1246/BCSJ.55.2236
SATOSHI HIBINO, EIICHI SUGINO, TOSHIHARU YAMOCHI, MASUKI KUWATA, HIROKO HASHIMOTO, KOHICHI SATO, FUSAO AMANUMA, YASUKO KARASAWA, Syntheses and sleeping-time-prolonging effect of nitramarine and related compounds. Chemical & Pharmaceutical Bulletin. ,vol. 35, pp. 2261- 2265 ,(1987) , 10.1248/CPB.35.2261