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Synthesis 2010(10): 1613-1616  
DOI: 10.1055/s-0029-1218714
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Recyclable Indium(III) Chloride Catalyzed Site-Selective Double Substitution in One Pot for the Synthesis of Isatin N-Ribonucleosides under Microwave Irradiation

Ibadur R. Siddiqui*a, Archana Singha, Shayna Shamima, Vishal Srivastavaa, Pravin K. Singha, Sanjay Yadava, Rana K. P. Singhb
a Laboratory of Green Synthesis, Department of Chemistry, University of Allahabad, Allahabad 211002, India
e-Mail: irsiddiquiau@rediffmail.com ;
b Electroorganic and Green Synthesis Laboratory, Department of Chemistry, University of Allahabad, Allahabad 211002, India
e-Mail: rkp.singh@rediffmail.com;
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Publication History

Received 22 January 2010
Publication Date:
26 March 2010 (online)

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Abstract

A novel one-pot synthesis of isatin N-ribonucleosides from N-phenylribosylamines and diethyl oxalate in ethanol catalyzed by recyclable indium(III) chloride under microwave irradiation has been developed. The transformation consists of indium(III) chloride catalyzed nucleophilic substitution by N-phenylribosyl­amines on diethyl oxalate followed by rapid intramolecular electrophilic substitution, which results in annulation of a five-membered nitrogen heterocycle on to the benzene ring yielding isatin N-ribonucleosides. The reaction proceeded smoothly in quantitative yields at ambient temperatures. The starting materials, N-phenylribosyl­amines, were prepared by indium(III) chloride catalyzed nucleophilic substitution of the anomeric hydroxy group of β-d-ribofuranose by an arylamine under microwave irradiation.

Key words

isatin N-ribonucleoside - indium(III) chloride - one-pot reaction - microwave - double substitution