Application of 2-substituted ethyl isothiocyanates and 2-aminothiols in the synthesis of the analogs of indole phytoalexin camalexin

…, P Kutschy, JP Tewari, V Kováčik

Index: Dzurilla, Milan; Ruzinsky, Martin; Kutschy, Peter; Tewari, Jalpa P.; Kovacik, Vladimir Collection of Czechoslovak Chemical Communications, 1999 , vol. 64, # 9 p. 1448 - 1456

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Citation Number: 18

Abstract

Abstract Treatment of (indol-1-yl) magnesium bromide or iodide with 2-bromoethyl isothiocyanate afforded 1-(4, 5-dihydrothiazol-2-yl) indole (6). Analogous reaction with 2, 2- dimethoxyethyl isothiocyanate led to corresponding 1-thiocarbamoylindole derivative (7), which was cyclized to 1-(5-methoxy-4, 5-dihydrothiazol-2-yl) indole (8) by treatment with boron trifluoride etherate. New analogs of camalexin, namely 4', 5'-dihydrocamalexin (12) ...