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CC BY 4.0 · Synthesis 2017; 49(12): 2753-2760
DOI: 10.1055/s-0036-1589496
DOI: 10.1055/s-0036-1589496
paper
Synthesis of Chromenoimidazoles, Annulated with an Azaindole Moiety, through a Base-Promoted Domino Reaction of Cyanomethyl Quaternary Salts
Further Information
Publication History
Received: 15 February 2017
Accepted after revision: 20 February 2017
Publication Date:
04 April 2017 (online)
Abstract
The reactivity of N-cyanomethyl quaternary salts of 4-, 5- and 7-azaindoles towards salicylic aldehydes has been studied. The interaction of azaindolium salts with salicylic aldehydes proceeds as a base-promoted domino reaction, giving the corresponding chromenoimidazopyrrolopyridines. In the case of the 7-(cyanomethyl)-7-azaindolium salt, the reaction was found to be more sensitive, but the use of the 1-methyl-substituted salt allowed the synthesis of the desired compounds, incorporating the heterocyclic core of isogranulatimide C, a marine natural product.
Key words
azaindoles - domino reaction - isogranulatimides - iminium salts - chromenoimidazoles - microwaveSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1558972.
- Supporting Information
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For our studies on the construction of fused chromenoimidazoles, see: