A novel synthesis of 3-cyanoindoles and a new route to indole-3-carboxylic acid derivatives
J Garcia, R Greenhouse, JM Muchowski, JA Ruiz
Index: Garcia, Josefina; Greenhouse, Robert; Muchowski, Joseph M.; Ruiz, Jose Antonio Tetrahedron Letters, 1985 , vol. 26, # 15 p. 1827 - 1830
Full Text: HTML
Citation Number: 13
Abstract
Abstract 2-Alkyl-3-cyanoindoles are obtained when 1-alkylmethyl-2-chloro-(or 2- phenylsulfonyl)-3-phenylsulfonylindoles are reacted with excess azide ion (90/DMF). The reaction is considered to occur by a fragmentation recombination process in which the Schiff's base 12 is of central importance. This proposal is supported by the formation of 2- substituted indole-3-carboxylates 17 from aldehydes and the α-phenylsulfonyl-o- ...
Related Articles:
Cyanation of indoles with benzyl cyanide as the cyanide anion surrogate
[Zhang, Lianpeng; Wen, Qiaodong; Jin, Jisong; Wang, Chen; Lu, Ping; Wang, Yanguang Tetrahedron, 2013 , vol. 69, # 21 p. 4236 - 4240]
[Wentrup, Curt; Lan, Nguyen Mong; Lukosch, Adelheid; Bednarek, Pawel; Kvaskoff, David Beilstein Journal of Organic Chemistry, 2013 , vol. 9, p. 743 - 753]
[Wentrup, Curt; Lan, Nguyen Mong; Lukosch, Adelheid; Bednarek, Pawel; Kvaskoff, David Beilstein Journal of Organic Chemistry, 2013 , vol. 9, p. 743 - 753]
[Abraham, Tonson; Sicree, Albert J. Monatshefte fuer Chemie, 1982 , vol. 113, p. 1063 - 1066]
Zinc??Catalyzed Direct Cyanation of Indoles and Pyrroles: Nitromethane as a Source of a Cyano Group
[Nagase, Yuta; Sugiyama, Tetsuya; Nomiyama, Shota; Yonekura, Kyohei; Tsuchimoto, Teruhisa Advanced Synthesis and Catalysis, 2014 , vol. 356, # 2-3 p. 347 - 352]