Synthesis of alkyl-substituted N-protected indoles via acylation and reductive deoxygenation

DM Ketcha, BA Lieurance, DFJ Homan…

Index: Ketcha, Daniel M.; Lieurance, Brett A.; Homan, Dominic F. J.; Gribble, Gordin W. Journal of Organic Chemistry, 1989 , vol. 54, # 18 p. 4350 - 4356

Full Text: HTML

Citation Number: 74

Abstract

The synthesis of 2-, 3-, and 5-alkyl-l-(phenylsulfonyl) indoles involving Friedel-Crafts acylation followed by reductive deoxygenation is described. The application of this acylation- deoxygenation sequence to 3-acyl-l-(phenylsulfony1) indoles bearing potentially reducible functionalities was explored using sodium borohydride in trifluoroacetic acid. While halogen atoms attached to the 2-position display a predictable range of lability toward this reducing ...

Related Articles:

An Unusual and Chemoselective Reduction of Ester Grouping in Nsubstituted-3-acetylindoles by Sodium Borohydride

[Venkatanarayana, Muvvala; Dubey, Pramod K. Letters in Organic Chemistry, 2012 , vol. 9, # 3 p. 192 - 197]

InCl 3 and In (OTf) 3 catalyzed reactions: synthesis of 3-acetyl indoles, bis-indolylmethane and indolylquinoline derivatives

[Nagarajan, Rajagopal; Perumal, Paramasivan T Tetrahedron, 2002 , vol. 58, # 6 p. 1229 - 1232]

Synthesis and quantitative structure–activity relationship (QSAR) study of novel N-arylsulfonyl-3-acylindole arylcarbonyl hydrazone derivatives as nematicidal agents

[Che, Zhiping; Zhang, Shaoyong; Shao, Yonghua; Fan, Lingling; Xu, Hui; Yu, Xiang; Zhi, Xiaoyan; Yao, Xiaojun; Zhang, Rui Journal of Agricultural and Food Chemistry, 2013 , vol. 61, # 24 p. 5696 - 5705]

Novel and Simple Methodology for the Synthesis of 3-Acetylindoles and their N-Alkyl Derivatives Using TBAB as Phase Transfer Catalyst

[Venkatanarayana; Dubey, Pramod K. Letters in Organic Chemistry, 2011 , vol. 8, # 9 p. 656 - 662]

Novel and Simple Methodology for the Synthesis of 3-Acetylindoles and their N-Alkyl Derivatives Using TBAB as Phase Transfer Catalyst

[Venkatanarayana; Dubey, Pramod K. Letters in Organic Chemistry, 2011 , vol. 8, # 9 p. 656 - 662]

More Articles...