CARBOXYL-MEDIATED PICTET-SPENGLER REACTION - DIRECT SYNTHESIS OF 1,2,3,4-TETRAHYDRO-BETA-CARBOLINES FROM TRYPTAMINE-2-CARBOXYLIC ACIDS

被引：40
|
作者：
NARAYANAN, K [1 ]
SCHINDLER, L [1 ]
COOK, JM [1 ]
机构：
[1] UNIV WISCONSIN,DEPT CHEM,MILWAUKEE,WI 53201
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 01期
关键词：
D O I：
10.1021/jo00001a066
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Pictet-Spengler condensation of various tryptamine-2-carboxylic acids 9a-f with carbonyl compounds in benzene/dioxane/trifluoroacetic acid (Table I) with simultaneous loss of carbon dioxide afforded directly the corresponding 1,2,3,4-tetrahydro-beta-carbolines 14a-j in good to excellent yields. This reaction greatly enhances the use of the Abramovitch-Shapiro method for the synthesis of highly oxygenated ring A substituted 1,2,3,4-tetrahydro-beta-carbolines (THBC). The lactams 14f,g and 14h are key intermediates for the synthesis of ring A substituted 1-methoxycanthin-6-one analogues.
引用
收藏
页码：359 / 365
页数：7
相关论文
共 50 条
  • [31] THE PICTET-SPENGLER REACTION OF ARYLGLYOXALS - A CONVENIENT SYNTHESIS OF 1-AROYL-1,2,3,4-TETRAHYDROISOQUINOLINES
    NIMGIRAWATH, S
    KAEWKET, S
    JOURNAL OF THE SCIENCE SOCIETY OF THAILAND, 1982, 8 (03): : 167 - 169
  • [32] SYNTHESIS AND PHARMACOLOGICAL PROPERTIES OF SOME 2-(3-AMINOPROPIONYL)-1-(3-PYRIDYL)-1,2,3,4-TETRAHYDRO-BETA-CARBOLINES AND 2-(3-AMINOPROPYL)-1-(3-PYRIDYL)-1,2,3,4-TETRAHYDRO-BETA-CARBOLINES
    MISZTAL, S
    BOKSA, J
    CHOJNACKAWOJCIK, E
    TATARCZYNSKA, E
    RUSSEVA, S
    POLISH JOURNAL OF PHARMACOLOGY AND PHARMACY, 1988, 40 (04): : 413 - 421
  • [33] SYNTHESIS OF 5-SUBSTITUTED 6-METHOXY-1,2,3,4-TETRAHYDRO-BETA-CARBOLINES
    URITSKAYA, MY
    ANISIMOVA, OS
    YAKHONTOV, LN
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1979, (01): : 80 - 85
  • [34] DOPAMINE ANALOGOUS 1,2,3,4-TETRAHYDRO-BETA-CARBOLINES .2. ALTERATION OF ACTIVITY BY SUBSTITUENTS
    REHSE, K
    PIESKER, G
    KEHR, W
    WACHTEL, H
    ARCHIV DER PHARMAZIE, 1979, 312 (07) : 597 - 603
  • [35] STEREOSPECIFIC SYNTHESIS OF TRANS-1,3-DISUBSTITUTED-1,2,3,4-TETRAHYDRO-BETA-CARBOLINES
    UNGEMACH, F
    DIPIERRO, M
    WEBER, R
    COOK, JM
    JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (01): : 164 - 168
  • [36] SYNTHESIS AND SOME PHARMACOLOGICAL PROPERTIES OF NEW 1,2,3-SUBSTITUTED 1,2,3,4-TETRAHYDRO-BETA-CARBOLINES
    POGOSYAN, SA
    MATEVOSYAN, LA
    MELIKOGANJANNYAN, AS
    SAFRAZBEKYAN, RR
    ARZANUNTS, EM
    SARKISYAN, IS
    PARONIKYAN, RG
    AKOPYAN, NE
    KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1986, 20 (10): : 1191 - 1195
  • [37] Synthesis of 4-substituted-1,2,3,4-tetrahydro-beta-carbolines via intramolecular radical cyclisation and Heck reaction
    Mohanakrishnan, AK
    Srinivasan, PC
    TETRAHEDRON LETTERS, 1996, 37 (15) : 2659 - 2662
  • [38] SYNTHESIS AND SEROTONIN-RECEPTOR ACTIVITY OF SUBSTITUTED 1-OXO-1,2,3,4-TETRAHYDRO-BETA-CARBOLINES
    HERDEIS, C
    BISSINGER, G
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1987, 42 (06): : 785 - 790
  • [39] STEREOSPECIFIC SYNTHESIS OF TRANS, CIS-1,3,4-TRISUBSTITUTED 1,2,3,4-TETRAHYDRO-BETA-CARBOLINES
    BEHFOROUZ, M
    WEST, SJ
    CHAKRABARTY, C
    RUSK, DA
    ZARRINMAYEH, H
    HETEROCYCLES, 1992, 34 (03) : 483 - 495
  • [40] A NEW METHOD FOR THE PREPARATION OF 3,4-DIHYDRO AND 1,2,3,4-TETRAHYDRO-BETA-CARBOLINES
    NAKAMURA, T
    ISHIDA, A
    IRIE, K
    OHISHI, T
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1984, 32 (07) : 2859 - 2862
12345