An expedient, regioselective synthesis of 2-alkylamino-and 2-alkylthiothiazolo [5, 4-e] indoles

M Chakrabarty, T Kundu, S Arima, Y Harigaya

Index: Chakrabarty, Manas; Kundu, Taraknath; Arima, Shiho; Harigaya, Yoshihiro Tetrahedron Letters, 2005 , vol. 46, # 16 p. 2865 - 2868

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Citation Number: 16

Abstract

1-Benzenesulfonyl-5-aminoindole, prepared from 5-nitroindole, was condensed with alkyl isothiocyanates and separately with carbon disulfide and alkyl bromides/iodides to furnish efficiently the corresponding N-alkyl-thioureidoindoles the alkyl N-(indol-5′-yl) dithiocarbamates, respectively. Their cyclisation using N-bromosuccinimide (NBS) and 1, 8- diazabicyclo [5.4. 0] undec-7-ene (DBU), in the cold, followed by indolic N-deprotection, ...