Three-Component Reaction of Aldose Sugars, Aryl Amines, and 1,3-Diones: A Novel Synthesis of Annulated Pyrroles

Aldose sugars undergo smooth coupling with enamines, generated in situ from aryl amines and 1,3-diketones, in the presence of 10 mol % of InCl3 in water at 80 °C to furnish annulated pyrrole derivatives in relatively good to high yields. The use of InCl3, in combination with water, makes this proced...

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Bibliographic Details
Published in:	Journal of organic chemistry Vol. 73; no. 8; pp. 3252 - 3254
Main Authors:	Yadav, Jhillu S., Subba Reddy, Basi V., Srinivas, Mende, Divyavani, Chitteti, Jeelani Basha, Shaik, Sarma, Akella V. S.
Format:	Journal Article
Language:	English
Published:	Washington, DC American Chemical Society 18-04-2008
Subjects:	Amines - chemistry Carbohydrates - chemistry Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Magnetic Resonance Spectroscopy Models, Molecular Molecular Structure Organic chemistry Preparations and properties Pyrroles - chemical synthesis Pyrroles - chemistry Water Annelation Aldose Nitrogen heterocycle Enamine Oside Indium III Chlorides Diketone Chemical synthesis Arylamine Pyrrole derivatives
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Summary:	Aldose sugars undergo smooth coupling with enamines, generated in situ from aryl amines and 1,3-diketones, in the presence of 10 mol % of InCl3 in water at 80 °C to furnish annulated pyrrole derivatives in relatively good to high yields. The use of InCl3, in combination with water, makes this procedure quite simple, more convenient, and environmentally friendly.
Bibliography:	ark:/67375/TPS-BDGK6V5B-J istex:17643178E97804FC2B9B07ADA66DA332E78E9286 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo702012w