Efficient Access to Azaindoles and Indoles
作者： Mark McLaughlin , Michael Palucki , Ian W. Davies
DOI: 10.1021/OL061232R
关键词:
摘要: [Structure: see text] An expedient, catalytic method for the synthesis of diverse azaindoles and indoles, starting from readily available inexpensive materials, is described. Conditions were developed effective reductive alkylation electron-deficient o-chloroarylamines, substrates previously viewed as poor partners in this reaction. The derived N-alkylated o-chloroarylamines elaborated to N-alkylazaindoles N-alkylindoles via a novel one-pot process comprising copper-free Sonogashira alkynylation base-mediated indolization
acs.org
sci-hub.se 参考文章(12)
Kenkichi Sonogashira, Yasuo Tohda, Nobue Hagihara, A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines Tetrahedron Letters. ,vol. 16, pp. 4467- 4470 ,(1975) , 10.1016/S0040-4039(00)91094-3
Ahmed F. Abdel-Magid, Kenneth G. Carson, Bruce D. Harris, Cynthia A. Maryanoff, Rekha D. Shah, Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures1 Journal of Organic Chemistry. ,vol. 61, pp. 3849- 3862 ,(1996) , 10.1021/JO960057X
Alain Louis Rodriguez, Christopher Koradin, Wolfgang Dohle, Paul Knochel, Versatile Indole Synthesis by a 5‐endo‐dig Cyclization Mediated by Potassium or Cesium Bases Angewandte Chemie. ,vol. 39, pp. 2488- 2490 ,(2000) , 10.1002/1521-3773(20000717)39:14<2488::AID-ANIE2488>3.0.CO;2-E
Gilson Zeni, Richard C. Larock, Synthesis of Heterocycles via Palladium π-Olefin and π-Alkyne Chemistry Chemical Reviews. ,vol. 104, pp. 2285- 2309 ,(2004) , 10.1021/CR020085H
Jeffrey T. Kuethe, Audrey Wong, Chuanxing Qu, Jacqueline Smitrovich, Ian W. Davies, David L. Hughes, Synthesis of 5-substituted-1H-indol-2-yl-1H-quinolin-2-ones: a novel class of KDR kinase inhibitors. Journal of Organic Chemistry. ,vol. 70, pp. 2555- 2567 ,(2005) , 10.1021/JO0480545
Dmitri Gelman, Stephen L. Buchwald, Efficient palladium-catalyzed coupling of aryl chlorides and tosylates with terminal alkynes: Use of a copper cocatalyst inhibits the reaction Angewandte Chemie. ,vol. 42, pp. 5993- 5996 ,(2003) , 10.1002/ANIE.200353015
Kevin W. Anderson, Stephen L. Buchwald, General Catalysts for the Suzuki–Miyaura and Sonogashira Coupling Reactions of Aryl Chlorides and for the Coupling of Challenging Substrate Combinations in Water Angewandte Chemie. ,vol. 44, pp. 6173- 6177 ,(2005) , 10.1002/ANIE.200502017
Dawei Yue, Richard C. Larock, Synthesis of 3-iodoindoles by electrophilic cyclization of N,N-dialkyl-2-(1-alkynyl)anilines. Organic Letters. ,vol. 6, pp. 1037- 1040 ,(2004) , 10.1021/OL0498996
Lutz Ackermann, General and efficient indole syntheses based on catalytic amination reactions. Organic Letters. ,vol. 7, pp. 439- 442 ,(2005) , 10.1021/OL047649J
Christopher Koradin, Wolfgang Dohle, Alain L Rodriguez, Bertram Schmid, Paul Knochel, Synthesis of polyfunctional indoles and related heterocycles mediated by cesium and potassium bases Tetrahedron. ,vol. 59, pp. 1571- 1587 ,(2003) , 10.1016/S0040-4020(03)00073-5