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p. 727
Published: 31 August 2003
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p. 728-734
Received: 19 December 2002; in revised form: 19 August 2003 / Accepted: 20 August 2003 / Published: 31 October 2003
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| Download PDF Full-text (53 KB) Abstract: Treatment of carboxylated Wang polymer attached to a 2-unsubstituted indole derivative with a trifluoroacetic acid based mixture resulted in a side reaction: p-hydroxybenzylation at the 2-position of the indole ring. The structure of the resulting N-3-aminopropyl)-N-benzyl-4-[2-(4-hydroxybenzyl)-1H-indol-3-yl]-butyramide trifluoroacetate was ascertained by a full assignment of its 1 H- and 13 C-NMR spectra. The side reaction could be suppressed by the use of 1,2-ethanedithiol in high concentrations (16 %).
p. 735-743
Received: 29 April 2003; in revised form: 17 August 2003 / Accepted: 18 August 2003 / Published: 31 October 2003
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| Download PDF Full-text (53 KB) Abstract: A general synthesis of tetronic acid derivatives, namely 4-aroyl-3-alkoxy-2(5H)-furanones, is achieved via the treatment of an anhydrous dimethylformamide (DMF) solution of 4-aroyl-3-hydroxy-2(5H)-furanones with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as base at -10-0°C, followed by the addition of alkyl iodide. Their structural assignments are based on spectroscopic data and confirmed by X-ray crystallography. These furanones were used as starting materials for the preparation of furodiazepines.
p. 744-755
Received: 1 June 2003; in revised form: 20 August 2003 / Accepted: 25 August 2003 / Published: 31 October 2003
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| Download PDF Full-text (108 KB) Abstract: Acylation of 3-hydrazino-5,6-diphenyl-1,2,4-triazine (2) and hydrazine hydrate (7) with 4-aryl-1,3,7-triphenyl-8-oxa-1,2,6-triazaspiro[4.4]nona-2,6-dien-9-ones 5a,b gave the corresponding heterocyclic carbohydrazides 6a,b and 8a,b respectively. Conversion of compounds 8a,b into the versatile carbohydrazide derivatives 9a-g, 10, 13 and the related oxadiazoles 11, 12a,b was undertaken. A primary in vitro test of compound 8a (concentration 10-4 M) showed activity against leukemia cell lines (CCRFCEM, K-256, MOLT-4, PRMI-8226, SR).
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