Tetrahedron

Synthesis of thiazino [6, 5-b] indole derivatives, analogues of the phytoalexin cyclobrassinin. A new method for preparation of 3-aminomethylindole

P Csomós, L Fodor, P Sohár, G Bernáth

Index: Csomos, Peter; Fodor, Lajos; Sohar, Pal; Bernath, Gabor Tetrahedron, 2005 , vol. 61, # 39 p. 9257 - 9262

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Citation Number: 16

Abstract

An efficient non-reductive synthesis of 3-aminomethylindole () was developed from gramine () via 3-phthalimidomethylindole (). The reactions of amine with substituted methyl dithiobenzoates gave 3-(arylthiocarbonylaminomethyl) indoles. The Hugerschoff ring- closure reactions of the thiobenzamide intermediates () with phenyltrimethylammonium tribromide and subsequent basic treatment furnished 2-arylthiazino [6, 5-b] indole ...