A NOVEL SYNTHESIS OF 3,4,5,6-TETRAHYDRO-7-HYDROXY-1H-AZEPINO[5,4,3-cd]INDOLE DERIVATIVES FROM SEROTONIN

被引：7
|
作者：
Yamada, Koji [1 ]
Teranishi, Sakiko [2 ]
Miyashita, Ayako [2 ]
Ishikura, Minoru [1 ]
Somei, Masanori [2 ]
机构：
[1] Hlth Sci Univ Hokkaido, Fac Pharmaceut Sci, Ishikari, Hokkaido 0610293, Japan
[2] Kanazawa Univ, Fac Pharmaceut Sci, Grad Sch Nat Sci & Technol, Kanazawa, Ishikawa 9201192, Japan
来源：
HETEROCYCLES | 2011年 / 83卷 / 11期
关键词：
Ab-Acylserotonin; Ab-Alkylserotonin; 3,4,5,6-Tetrahydro-7-hydroxy-1H-azepino[5,4,3-cd]indole; 1H-Azepino[5,4,3-cd]indole-2-one; Serotonin; SHORT STEP SYNTHESIS; ERGOT ALKALOIDS; 1-HYDROXYINDOLE DERIVATIVES; BROMOMELATONIN DERIVATIVES; COMBATING DESERTIFICATION; PLATELET-AGGREGATION; BONE-DISEASES; CHEMISTRY; INDOLES; 1-HYDROXYTRYPTAMINES;
D O I：
10.3987/COM-11-12345
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Utilizing novel Nb-substituted serotonins, 5- and/or 6-substituted 3,4,5,6-tetrahydro-7-hydroxy-1H-azepino[5,4,3-cd]indole derivatives are produced simply by treating serotonins with aldehydes under basic conditions. Synthesis of 2,2a,3,4,5,6-hexahydro-7-hydroxy-1H-azepino[5,4,3-cd]indole-2-one derivatives is also reported.
引用
收藏
页码：2547 / 2562
页数：16
相关论文
共 50 条
  • [21] 3,4,5,6-TETRAHYDRO-2H,1,5-BENZOXAZOCINE - NOVEL HETEROCYCLIC SYSTEM
    BERG, SS
    TOFT, MP
    SYNTHETIC COMMUNICATIONS, 1976, 6 (03) : 175 - 183
  • [22] SYNTHESIS OF 4,5-DISUBSTITUTED 1H-1,3,4,5-TETRAHYDRO-BENZ[CD]INDOLE DERIVATIVES
    GALAMBOS, G
    CSOKASI, P
    SZANTAY, C
    CZIRA, G
    SZANTAY, C
    HETEROCYCLES, 1994, 38 (08) : 1727 - 1732
  • [23] PHOTOCYCLIZATIONS .3. SYNTHESIS OF 3,6-DIMETHYL-8-HYDROXY-3,4,5,6-TETRAHYDRO-3-BENZAZOCIN -2(H-1)-ONE
    ONG, HH
    MAY, EL
    JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (05): : 924 - 927
  • [24] SYNTHESIS OF NOVEL ISOXAZOLYL 3,4,5,6-TETRAHYDRO-2H-1,3,5-BENZOXADIAZOCIN-4-ONES AS POSSIBLE BIODYNAMIC AGENTS
    Rajanarendar, E.
    Raju, S.
    Reddy, M. Nagi
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 19 (03) : 265 - 268
  • [25] A chemoenzymatic synthesis of 3,4,5,6-tetrahydro-2H-benzo[b][1,4]-oxazocine-3,5-dione and its derivatives
    Ch. Sree Lakshmi
    H. Rehaman
    Adari Bhaskar Rao
    Monatshefte für Chemie - Chemical Monthly, 2009, 140
  • [26] A chemoenzymatic synthesis of 3,4,5,6-tetrahydro-2H-benzo[b][1,4]-oxazocine-3,5-dione and its derivatives
    Lakshmi, Ch. Sree
    Rehaman, H.
    Rao, Adari Bhaskar
    MONATSHEFTE FUR CHEMIE, 2009, 140 (06): : 611 - 613
  • [27] Synthesis of novel pipecolic acid derivatives:: a multicomponent approach from 3,4,5,6-tetrahydropyridines
    Maison, W
    Lützen, A
    Kosten, M
    Schlemminger, I
    Westerhoff, O
    Martens, J
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (23): : 3515 - 3525
  • [28] SYNTHESIS AND DOPAMINE-RECEPTOR BINDING OF 3-PHENYLAZEPINO[5,4,3-C,D]INDOLE DERIVATIVES
    GMEINER, P
    SOMMER, J
    HOFNER, G
    ARCHIV DER PHARMAZIE, 1995, 328 (04) : 329 - 332
  • [29] Synthesis of 4,7,8a,9-tetrahydro-3H-diindazo[1,5-a:4′,5′-d]pyridine derivatives
    Braña, MF
    Guisado, C
    Pérez-Castells, J
    Pérez-Serrano, L
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (02) : 417 - 420
  • [30] Studies on pyrazine derivatives, XLIV:: Synthesis and tuberculostatic activity of 4-substituted 3,4,5,6-tetrahydro-2H-[1,2′]-bis-pyrazine derivatives
    Foks, H
    Pancechowska-Ksepko, D
    Janowiec, M
    Zwolska, Z
    Augustynowicz-Kopec, E
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2005, 180 (11) : 2543 - 2548
12345