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Synthesis 2014; 46(16): 2175-2178
DOI: 10.1055/s-0033-1341237
DOI: 10.1055/s-0033-1341237
paper
An Efficient Synthesis of Nitrated Cycloalka[b]pyridines
Further Information
Publication History
Received: 27 February 2014
Accepted after revision: 26 March 2014
Publication Date:
08 May 2014 (online)
Abstract
The three-component ring transformation of 1-methyl-3,5-dinitro-2-pyridone with cycloalkanones of different ring sizes in the presence of ammonium acetate affords the corresponding nitrated cycloalka[b]pyridines in high yields. Furthermore, a double bond can be easily introduced into the product by changing the cycloalkanone into a cycloalkenone.
Key words
pyridines - multicomponent reaction - ketones - heterocycles - bicyclic compounds - ring transformationSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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The TCRT of 3-methyl-5-nitro-4-pyrimidinone with ketone in the presence of NH4OAc proceeds efficiently to afford pyrimidines, nitropyridones, and aminopyridines, see: