Synthesis of indolylalkylphosphonates and 3-(1-diphenylphosphinoalkyl) indoles by reaction of 3-(1-arylsulfonlyalkyl) indoles with phosphorus derivatives

被引：18
|
作者：
Petrini, Marino [1 ]
Shaikh, Rafik R. [1 ]
机构：
[1] Univ Camerino, Dipartimento Sci Chim, I-62032 Camerino, Italy
来源：
TETRAHEDRON LETTERS | 2008年 / 49卷 / 39期
关键词：
conjugate addition; imines; indoles; phosphines; phosphites; sulfones;
D O I：
10.1016/j.tetlet.2008.07.077
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Dialkyl phosphites as well as diphenylphosphine react with 3-(1-arylsulfonylalkyl) indoles under basic conditions leading to a formal substitution of the arylsulfonyl group through a reactive 3-alkylidene indole intermediate. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5645 / 5648
页数：4
相关论文
共 50 条
  • [1] Synthesis of 3-(2-nitroalkyl) indoles by reaction of 3-(1-arylsulfonylalkyl) indoles with nitroalkanes
    Palmieri, Alessandro
    Petrini, Marino
    Torregiani, Elisabetta
    TETRAHEDRON LETTERS, 2007, 48 (32) : 5653 - 5656
  • [2] Synthesis of 3-[(1-aryl)aminomethyl]indoles
    Wynne, JH
    Stalick, WM
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16): : 5850 - 5853
  • [3] Simplified synthesis of 3-(1-arylsulfonylalkyl) indoles and their reaction with Reformatsky reagents
    Palmieri, Alessandro
    Petrini, Marino
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (05): : 1863 - 1866
  • [4] Synthesis and biological evaluation of 3-(azolylmethyl)-1H-indoles and 3-(α-azolylbenzyl)-1H-indoles as selective aromatase inhibitors
    Le Borgne, Marc
    Marchand, Pascal
    Nourrisson, Marie-Renee
    Loquet, Denis
    Palzer, Martina
    Le Baut, Guillaume
    Hartmann, Rolf W.
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2007, 22 (05) : 667 - 676
  • [5] SYNTHESIS OF 2-(CHLOROMERCURI)INDOLES AND 3-(CHLOROMERCURI)INDOLES
    YUDIN, LG
    PAVLYUCH.AI
    KOST, AN
    JOURNAL OF GENERAL CHEMISTRY USSR, 1969, 39 (12): : 2719 - &
  • [6] 3-(Tetrahydropyridinyl)indoles
    Gharagozloo, P
    Miyauchi, M
    Birdsall, NJM
    TETRAHEDRON, 1996, 52 (30) : 10185 - 10192
  • [7] AN EFFICIENT SYNTHESIS OF 3-[1-(3-PYRIDYL)ETHYL]INDOLES
    SAINSBURY, M
    WEERASINGHE, DK
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (13) : 630 - 631
  • [8] SYNTHESIS AND ANTIMYCOTIC ACTIVITY OF SOME 3-(1-IMIDAZOLYLMETHYL)INDOLES
    GATTI, R
    CAVRINI, V
    ROVERI, P
    LUGLIO, G
    ARCHIV DER PHARMAZIE, 1985, 318 (02) : 157 - 160
  • [9] Synthesis and antifungal activity of 3-(1,3,4-oxadiazol-5-yl)-indoles and 3-(1,3,4-oxadiazol-5-yl)methyl-indoles
    Zhang, Ming-Zhi
    Mulholland, Nick
    Beattie, David
    Irwin, Dianne
    Gu, Yu-Cheng
    Chen, Qiong
    Yang, Guang-Fu
    Clough, John
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 63 : 22 - 32
  • [10] Efficient Synthesis of 3-(Arenesulfinyl)indoles in Water
    Liu, Y.
    Zhang, Z. Y.
    Ji, Y. Z.
    Li, H. J.
    Wu, Y. C.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 57 (05) : 831 - 841
12345