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Synthesis 2017; 49(03): 637-646
DOI: 10.1055/s-0036-1588605
DOI: 10.1055/s-0036-1588605
paper
Brønsted Acid Catalyzed Selective Cyclization Reaction: An Efficient and Facile Synthesis of Polysubstituted Imidazole and Pyrrole Derivatives
Further Information
Publication History
Received: 31 August 2016
Accepted after revision: 02 September 2016
Publication Date:
06 October 2016 (online)
Abstract
An efficient and facile synthesis of 3-(5-aryl-1,3-dimethyl-2-oxo-2,3-dihydro-1H-imidazol-4-yl)indolin-2-one and 3-(2,5-diaryl-3-oxo-1,2,3,6-tetrahydropyrrolo[2,3-c]pyrazol-4-yl)indolin-2-one derivatives is reported from the selective cyclization reaction of 3-(2-aryl-2-oxoethylidene)indolin-2-one and 1,3-dimethylurea or 5-amino-2-phenyl-2,4-dihydro-3H-pyrazol-3-one under Brønsted acid conditions. Although there are two carbonyl groups in the substrate, the carbonyl group out of isatin is specially chosen for the cyclization reaction to give the target products. The reported products are new five-membered heterocyclic compounds and the results also show that p-toluenesulfonic acid monohydrate (PTSA·H2O) is an effective catalyst for this synthesis. Therefore, the advantages of this approach are excellent yields, short reaction times, operational simplicity, and good regioselectivity.
Key words
imidazole - pyrrole - 3-(2-aryl-2-oxoethylidene)indolin-2-one - Brønsted acid - cyclization reactionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588605.
- Supporting Information
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