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

被引：25

作者：

Chakrabarty, M

Kundu, T

Arima, S

Harigaya, Y

机构：

[1] Bose Inst, Dept Chem, Kolkata 700009, W Bengal, India

[2] Kitasato Inst, Sch Pharmaceut Sci, Minato Ku, Tokyo 108, Japan

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 16期

关键词：

thiazolo[5,4-e]indoles; regioselective synthesis; thioureido-indoles; indolyldithiocarbamates; NBS-DBU;

D O I：

10.1016/j.tetlet.2005.02.125

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Benzenesulfonyl-5-aminoindole 5, prepared from 5-nitroindole 3, was condensed with alkyl isothiocyanates and separately with carbon disulfide and alkyl bromides/iodides to furnish efficiently the corresponding N-alkyl-thioureidoindoles 6a-c and the alkyl N'-(indol-5'-yl)dithiocarbamates 9a-e, 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, furnished regioselectively the 2-alkylamino- and the 2-alkylthiothiazolo[5,4-e]indoles 8a-c and 11a-e, respectively, in good overall yields. (c) 2005 Elsevier Ltd. All rights reserved.

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页码：2865 / 2868

页数：4

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