METAL TRIFLUOROPYRUVATE IN THE PICTET-SPENGLER REACTION

被引:0
|
作者
GOLUBEV, AS
CHKANIKOV, ND
ANTIPIN, MY
STRUCHKOV, YT
KOLOMIETS, AF
FOKIN, AV
机构
来源
BULLETIN OF THE RUSSIAN ACADEMY OF SCIENCES-DIVISION OF CHEMICAL SCIENCE | 1992年 / 41卷 / 08期
关键词
METHYL TRIFLUOROPYRUVATE; 2-(3,4-DIMETHOXYPHENYL)ETHYLAMINE; TRYPTAMINE; (D; L)-TRYPTOPHAN; PICTET-SPENGLER REACTION; 1,2,3,4-TETRAHYDROISOQUINOLINES; 1,2,3,4-TETRAHYDRO-BETA-CARBOLINES;
D O I
10.1007/BF00864340
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Condensation of methyl trifluoropyruvate with 2-(3,4-dimethoxyphenyl)ethylamine, tryptamine, and (D, L)-tryptophan yielded 1-methoxycarbonyl-1-trifluoromethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline, 1-methoxycarbonyl-1-trifluoromethyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole, and Z-1-methoxycarbonyl-1-trifluoromethyl-3-carboxy-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole, respectively. The Z configuration of the latter was determined by x-ray structural analysis.
引用
收藏
页码:1425 / 1429
页数:5
相关论文
共 50 条
  • [31] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION
    COX, ED
    COOK, JM
    CHEMICAL REVIEWS, 1995, 95 (06) : 1797 - 1842
  • [32] Enantioselective Gold-Catalyzed Pictet-Spengler Reaction
    Glinsky-Olivier, Nicolas
    Yang, Shengwen
    Retailleau, Pascal
    Gandon, Vincent
    Guinchard, Xavier
    ORGANIC LETTERS, 2019, 21 (23) : 9446 - 9451
  • [33] Synthetic versus Enzymatic Pictet-Spengler Reaction: An Overview
    Sharma, Sachin
    Joshi, Gaurav
    Kalra, Sourav
    Singh, Sandeep
    Kumar, Raj
    CURRENT ORGANIC SYNTHESIS, 2018, 15 (07) : 924 - 939
  • [34] ISOSALSOLINOL FORMATION - SECONDARY REACTION IN PICTET-SPENGLER CONDENSATION
    KING, GS
    GOODWIN, BL
    SANDLER, M
    JOURNAL OF PHARMACY AND PHARMACOLOGY, 1974, 26 (06) : 476 - 478
  • [35] Application of the Pictet-Spengler reaction in combinatorial chemistry.
    Mayer, JP
    BankaitisDavis, D
    Zhang, JW
    Beaton, G
    Bjergarde, K
    Andersen, CM
    Goodman, BA
    Herrera, CJ
    TETRAHEDRON LETTERS, 1996, 37 (32) : 5633 - 5636
  • [36] Enantioselective asymmetric Pictet-Spengler reaction catalyzed by diisopinocampheylchloroborane
    Kawate, T
    Yamada, H
    Soe, T
    Nakagawa, M
    TETRAHEDRON-ASYMMETRY, 1996, 7 (05) : 1249 - 1252
  • [37] Oxidative Pictet-Spengler Cyclizations
    Hyun, Jin Kim
    Ung Chan Yoon
    Jung, Y.-S.
    No Sang Park
    Journal of Organic Chemistry, 63 (03):
  • [38] Oxidative Pictet-Spengler cyclizations
    Kim, HJ
    Yoon, UC
    Jung, YS
    Park, NS
    Cederstrom, EM
    Mariano, PS
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03): : 860 - 863
  • [39] Role of the acid group in the Pictet-Spengler reaction of α-amino acids
    de la Figuera, Natalia
    Fiol, Sandra
    Fernandez, Joan-Carles
    Forns, Pilar
    Fernandez-Forner, Dolors
    Albericio, Fernando
    SYNLETT, 2006, (12) : 1903 - 1907
  • [40] USE OF BETA-KETO-ALDEHYDES IN THE PICTET-SPENGLER REACTION
    SCHUT, RN
    CHEMISTRY & INDUSTRY, 1960, (40) : 1246 - 1247