22908-28-7Relevant articles and documents
Novel synthesis of benzofuran- and indol-2-yl-methanamine derivatives
Schlosser, Joachim,Johannes, Eugen,Zindler, Melanie,Lemmerhirt, Jan,Sommer, Benjamin,Schütt, Martin,Peifer, Christian
, p. 89 - 94 (2015/02/02)
We report on a novel synthesis towards benzofuran-2-yl-methanamine and indol-2-yl-methanamine derivatives by using ortho-methoxy and ortho-nitro substituted phenylacetic acids as starting material, respectively. For each compound series, a key intermediate bearing the oxazole-4-carboxylic acid methylester moiety was produced. Refluxing the ortho-methoxy series in HBr/HAc produced the desired benzofuran-2-yl-methanamines. Accordingly, for the synthesis of indoles the nitro-group was first reduced and refluxing these intermediates in HCl gave the corresponding indol-2-yl-methanamines. The method worked well with electron donating substituents. Limitations regarding electron withdrawing substituents are discussed. This straightforward synthetic procedure can be a useful approach to generate a variety of substituted benzofuran-2-yl-methanamine and indol-2-yl-methanamine compounds by starting from readily available phenylacetic acid derivatives.
An aminoisoflavone-salicyloylindole ring transformation
Loewe, Werner,Witzel, Sonja,Tappmeyer, Silvia,Albuschat, Rica
, p. 317 - 326 (2007/10/03)
A series of 2′-nitroisoflavones 8-10, 15, 22, 27 and 28 was prepared via the (2-nitro-phenyl)-acetic acids 1, 13, 19 and 25. In order to obtain the corresponding 2′-aminoisoflavones the reduction of 8-10, 15, 22, 27 and 28 was undertaken. Surprisingly, new 3-salicyloylindoles instead of the expected 2′-aminoisoflavones were the main reduction products. In the following paper the preparation of the 2′-nitroisoflavones 8-10, 15, 22, 27 and 28 as well as the reduction experiments obtaining the 2′-aminoisoflavones 33 and 35 and the 3-salicyloylindoles 29-32, 34 and 36 will be described. Furthermore, a possible mechanism responsible for the formation of the 3-salicyloylindoles from 2′-nitroisoflavones under reductive conditions will be discussed.