The Journal of Organic Chemistry

Synthesis of substituted indoles via Meerwein arylation

S Raucher, GA Koolpe

Index: Raucher, Stanley; Koolpe, Gary A. Journal of Organic Chemistry, 1983 , vol. 48, # 12 p. 2066 - 2069

Full Text: HTML

Citation Number: 65

Abstract

Meerwein arylation of 4methoxy-2-nitrobenzenediazonium chloride with formaldoxime to afford 2-nitroanisaldehyde; condensation with nitromethane and reductive cyclization afforded 6-methoxyindole, a necessary intermediate in the total synthesis of reserpine.'Meerwein arylation of 2-nitrobenzenediazonium chloride with 1, 3-butadiene, followed by ozonolysis of the resulting 1-(2-nitrophenyl)-4-chloro-2-butene and reductive ...

~76%

~64%

~70%

~54%

~53%

~13%

An annulative approach to highly substituted indoles: Unusua...

[Rutherford, Jennifer L.; Rainka, Matthew P.; Buchwald, Stephen L. Journal of the American Chemical Society, 2002 , vol. 124, # 51 p. 15168 - 15169]

A scalable method for regioselective 3-acylation of 2-substi...

[Coffman, Keith C.; Palazzo, Teresa A.; Hartley, Timothy P.; Fettinger, James C.; Tantillo, Dean J.; Kurth, Mark J. Organic Letters, 2013 , vol. 15, # 8 p. 2062 - 2065]

A Practical Synthesis of α-Aryl Methyl Ketones via a Transit...

[Molinaro, Carmela; Mowat, Jeffrey; Gosselin, Francis; O'Shea, Paul D.; Marcoux, Jean-Francois; Angelaud, Remy; Davies, Ian W. Journal of Organic Chemistry, 2007 , vol. 72, # 5 p. 1856 - 1858]

Nitric acid in dichloromethane solution. Facile preparation ...

[Strazzolini, Paolo; Giumanini, Angelo G.; Runcio, Antonio Tetrahedron Letters, 2001 , vol. 42, # 7 p. 1387 - 1389]

Altes und Neues über aliphatische Diazoverbindungen

[Arndt; Eistert; Partale Chemische Berichte, 1928 , vol. 61, p. 1112]