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Synthesis 2019; 51(06): 1445-1454
DOI: 10.1055/s-0037-1610319
DOI: 10.1055/s-0037-1610319
paper
Metal- and Solvent-free Synthesis of Functionalized Dihydrooxazolo[3,2-a]indoles by One-Pot Tandem Assembly of 3H-Indoles and Propargylic Alcohols
This work was supported by the Russian Foundation for Basic Research (grant no. 17-03-00927). The main results were obtained with the equipment of Baikal Analytical Center for collective use SB RAS.Further Information
Publication History
Received: 10 September 2018
Accepted after revision: 18 October 2018
Publication Date:
28 November 2018 (online)
Abstract
The reaction of 3H-indoles with tertiary propargylic alcohols to give functionalized dihydrooxazolo[3,2-a]indoles in good to excellent yields has been developed. This metal- and solvent-free, one-pot tandem assembly proceeds under mild conditions (22–60 °C) and is regio- and stereoselective: either the Z- or E-isomers (relative to the double bond) are alternatively formed depending on other functionalized substituents on the propargylic alcohols.
Key words
3H-indole - 1H-benzo[e]indole - propargylic alcohols - annulation - dihydrooxazolo[3,2-a]indolesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610319.
- Supporting Information
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