Intramolecular Mannich reaction of 2-oxotryptamines with acetone yielding spiro[indole-3,3′-pyrrolidin]-2-ones

被引:4
|
作者
Incze, M [1 ]
Dörnyei, G [1 ]
Kajtár-Peredy, M [1 ]
Szántay, C [1 ]
机构
[1] Hungarian Acad Sci, Inst Chem, Chem Res Ctr, H-1025 Budapest 2, Hungary
关键词
intramolecular Mannich reaction; spirocyclic compounds; indoles; pyrrolidines; cyclizations; alkaloids;
D O I
10.1135/cccc19990408
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
2-Oxotryptamines undergo intramolecular Mannich-type cyclization with acetone to give 2',2'-dimethylspiro[indole-3,3'-pyrrolidin]-2-ones. In presence of an alkylating reagent, this reaction gives the corresponding 1'-substituted products.
引用
收藏
页码:408 / 416
页数:9
相关论文
共 50 条
  • [1] Synthesis of novel spiro[indole-3,3′-pyrrolidin]-2(1H)-ones
    G. A. Gazieva
    N. G. Kolotyrkina
    A. N. Kravchenko
    N. N. Makhova
    Russian Chemical Bulletin, 2014, 63 : 431 - 434
  • [2] Synthesis of novel spiro[indole-3,3′-pyrrolidin]-2(1H)-ones
    Gazieva, G. A.
    Kolotyrkina, N. G.
    Kravchenko, A. N.
    Makhova, N. N.
    RUSSIAN CHEMICAL BULLETIN, 2014, 63 (02) : 431 - 434
  • [3] Synthesis of Spiro[indole-3,3′-pyrrolidine]-2′-(thi)ones
    Yasui, Motohiro
    Ohbu, Haruna
    Ishikawa, Maho
    Yoshida, Tatsuhito
    Takeda, Norihiko
    Hirao, Seiya
    Abe, Takumi
    Ueda, Masafumi
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (02): : 1093 - 1106
  • [4] A convenient synthetic route to spiro[indole-3,4′-piperidin]-2-ones
    Freund, R
    Mederski, WWKR
    HELVETICA CHIMICA ACTA, 2000, 83 (06) : 1247 - 1255
  • [5] STUDIES IN SPIRO HETEROCYCLES .4. INVESTIGATION OF THE REACTIONS OF FLUORINATED 3-AROYLMETHYLENE-INDOL-2-ONES WITH HYDRAZINE AND PHENYLHYDRAZINE AND SYNTHESIS OF SPIRO [INDOLE-3,3'-PYRAZOL]-2-ONES
    JOSHI, KC
    JAIN, R
    GARG, S
    PHARMAZIE, 1985, 40 (01): : 21 - 22
  • [7] SYNTHESES OF NOVEL SPIRO-[INDOLINE-3,3′-PYRAZOL]-2-ONES
    Havaldar, Freddy H.
    Burudkar, Sandeep M.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2011, 21 (01) : 23 - 28
  • [8] Rapid and facile synthesis of spiro[indole-3,3′-[1,2,4]triazol]-2(1H)-ones
    Mohamed, Ashraf M.
    Alsharari, Musaed A.
    Aly, Ashraf A.
    JOURNAL OF CHEMICAL RESEARCH, 2010, (04) : 200 - 202
  • [9] Synthesis of novel spiro-[3H-indole-3,3′-[1,2,4]triazolidine]-2-ones via azomethine imines
    Azizian, J
    Morady, AV
    Soozangarzadeh, S
    Asadi, A
    TETRAHEDRON LETTERS, 2002, 43 (52) : 9721 - 9723
  • [10] Highly regio- and stereoselective 1,3-dipolar cycloaddition of stabilised azomethine ylides to 3,3,3-trihalogeno-1-nitropropenes: synthesis of trihalomethylated spiro[indoline-3,2'-pyrrolidin]2-ones and spiro[indoline-3,3'-pyrrolizin]-2-ones
    Barkov, Alexey Yu.
    Zimnitskiy, Nikolay S.
    Korotaev, Vladislav Yu.
    Kutyashev, Igor B.
    Moshkin, Vladimir S.
    Sosnovskikh, Vyacheslav Ya.
    TETRAHEDRON, 2016, 72 (43) : 6825 - 6836