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Synthesis 2020; 52(15): 2267-2276
DOI: 10.1055/s-0040-1707471
DOI: 10.1055/s-0040-1707471
paper
Direct Synthesis of 5-Acyl-3-oxy-4-pyrones Based On Acid-Catalyzed Acylation of Enaminodiones with Acylbenzotriazoles via Soft Enolization
This work was financially supported by the Russian Science Foundation (Grant 18-73-00186).Further Information
Publication History
Received: 02 March 2020
Accepted after revision: 21 March 2020
Publication Date:
16 April 2020 (online)
Abstract
A novel convenient acid-catalyzed acylation of enaminodiones with acylbenzotriazoles via soft enolization has been developed for the direct synthesis of hard-to-reach 5-acyl-3-oxy-4-pyrones. The important advantages of the reaction include broad substrate scope, mild conditions, scalability, and readily isolation of products by crystallization without the use of chromatography. Further modification of the pyrone ring and synthesis of various azaheterocycles via ring-opening transformation have been demonstrated for the preparation of potential scaffolds for inhibition of metalloenzymes.
Key words
5-acyl-3-oxy-4-pyrone - enaminodiketone - soft enolization - acylbenzotriazole - debenzylation - ring-openingSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707471.
- Supporting Information
Primary Data
- Primary Data
for this article are available online at https://doi.org/10.1055/s-0040-1707471 and can be cited using the following DOI: 10.4125/pd0117th.
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