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Synthesis 2015; 47(10): 1436-1446
DOI: 10.1055/s-0034-1380174
DOI: 10.1055/s-0034-1380174
paper
Unusual Formal 1,2-Addition of Pyrazolones to 3-Indolylmethanols: Regiospecific Synthesis of 2,3-Disubstituted Indoles
Further Information
Publication History
Received: 15 November 2014
Accepted after revision: 16 January 2015
Publication Date:
26 February 2015 (online)
Abstract
An unusual formal 1,2-addition reaction of pyrazol-5-ones with isatin-derived 3-indolylmethanols has been established, which is suggested to proceed via a cascade reaction sequence of oxa-Michael addition, [3,3] rearrangement, 1,3-H shift and tautomerization. During the proposed reaction pathway, [3,3]-sigmatropic rearrangement of the oxa-Michael addition product is thought to be the key step leading to the regiospecific formal 1,2-addition reaction. This approach not only provides an easy access to 2,3-disubstituted indoles, but also has realized the rarely reported formal 1,2-addition of 3-indolylmethanols with regiospecificity, which opens a new window for investigations on 3-indolylmethanol-involved transformations.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380174.
- Supporting Information
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