A scalable method for regioselective 3-acylation of 2-substituted indoles under basic conditions
H Johansson, A Urruticoechea, I Larsen…
Index: 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
Full Text: HTML
Citation Number: 8
Abstract
... J. Org. ... Using indole 5 we screened acylation conditions with chloroacetyl chloride 6 and a series of organic bases with basicity ranging from moderate to ... procedure: indole (1 mmol), DCE (3 mL/mmol indole) and DBU (1.2 equiv) were mixed and heated to 90 °C under argon ...
Related Articles:
[Rutherford, Jennifer L.; Rainka, Matthew P.; Buchwald, Stephen L. Journal of the American Chemical Society, 2002 , vol. 124, # 51 p. 15168 - 15169]
A Practical Synthesis of α-Aryl Methyl Ketones via a Transition-Metal-Free Meerwein Arylation
[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]
Synthesis of substituted indoles via Meerwein arylation
[Raucher, Stanley; Koolpe, Gary A. Journal of Organic Chemistry, 1983 , vol. 48, # 12 p. 2066 - 2069]
Nitric acid in dichloromethane solution. Facile preparation from potassium nitrate and sulfuric acid
[Strazzolini, Paolo; Giumanini, Angelo G.; Runcio, Antonio Tetrahedron Letters, 2001 , vol. 42, # 7 p. 1387 - 1389]
Synthesis of substituted indoles via Meerwein arylation
[Raucher, Stanley; Koolpe, Gary A. Journal of Organic Chemistry, 1983 , vol. 48, # 12 p. 2066 - 2069]