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Synthesis 2019; 51(06): 1482-1490
DOI: 10.1055/s-0037-1610312
DOI: 10.1055/s-0037-1610312
paper
Convenient Synthesis of Ethyl 5-Oxohomoadamantane-4-carboxylate: A Useful Precursor of Polyfunctional Homoadamantanes
The research was supported by the Ministry of Education and Science of the Russian Federation within the framework of the Project part of the State Assignment No. 4.6764.2017/BC and Russian Foundation for Basic Research (Project No. 16-43-630823 A).Further Information
Publication History
Received: 03 September 2018
Accepted after revision: 12 October 2018
Publication Date:
08 November 2018 (online)
Abstract
A facile and convenient synthesis of ethyl 5-oxohomoadamantane-4-carboxylate is reported, and its chemical properties as a cage analogue of acetoacetic ester are investigated. Various derivatives of homoadamantane were synthesized through the reaction of 5-oxohomoadamantane-4-carboxylate with electrophilic agents, binucleophiles, and hydrazoic acid. Some new unusual products were obtained by the reaction of that β-keto ester with nitric acid and nitrosyl chloride. Cage compounds synthesized could be used as precursors for the diverse condensed heterocyclic compounds with potential viral ion channel abrogating activity that possess conformationally rigid lipophilic moieties.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610312.
- Supporting Information
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