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Synthesis 2020; 52(14): 2111-2120
DOI: 10.1055/s-0040-1707999
DOI: 10.1055/s-0040-1707999
paper
Regioselective Synthesis of Isomeric 3-[1-Substituted Pyrazol-3(5)-yl]indoles from β-Ethylthio-β-indolyl-α,β-unsaturated Ketones
This work was supported by the Foundation of Science and Technology Research Projects of the 13th Five-Year Plan of Education Department of Jilin Province [JJKH20200001KJ, the National Natural Science Foundation of China (No. 20902010) and the Jilin Scientific and Technological Development Program [20130206109SF].Further Information
Publication History
Received: 08 February 2020
Accepted after revision: 25 February 2020
Publication Date:
30 March 2020 (online)
Abstract
An efficient and highly regioselective synthesis of isomeric 3-[1-substituted pyrazol-3(5)-yl]indoles has been developed by the acid-mediated regioselective cyclocondensation reaction of β-ethyltho-β-indolyl-α,β-unsaturated ketones and monosubstituted hydrazines. In the presence of 1 equivalent of AcOH in refluxing EtOH, the cyclocondensation reaction of β-ethyltho-β- indolyl-α,β-unsaturated ketones with monosubstituted hydrazines yielded 3-(1-substituted pyrazol-5-yl)indoles in excellent yields, while 3-(1-substituted pyrazol-3-yl)indoles were obtained in good yields when the cyclocondensation reaction was carried out in refluxing AcOH.
Key words
β-ethylthio-β-indolyl-α,β-unsaturated ketones - acetic acid - pyrazoles - indoles - regioselective synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707999.
- Supporting Information
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