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Synthesis 2020; 52(09): 1398-1406
DOI: 10.1055/s-0039-1690053
DOI: 10.1055/s-0039-1690053
paper
Synthesis of 4-Nitroisoxazoles via NO/NO2-Mediated Heterocyclization of Aryl-Substituted α,β-Unsaturated Ketones
This work was supported by the Russian Science Foundation, grant no. 19-73-00145.Further Information
Publication History
Received: 10 December 2019
Accepted after revision: 13 January 2020
Publication Date:
03 February 2020 (online)
Abstract
A straightforward approach for the synthesis of 4-nitroisoxazoles has been developed via heterocyclization of aryl/hetaryl-substituted α,β-unsaturated ketones upon treatment with tetranitromethane-triethylamine (TNM-TEA) complex or t-BuONO. This strategy features high efficiency and wide substrate tolerance under simple reaction conditions.
Key words
4-nitroisoxazoles - alkenes - ketones - heterocycles - ring closure - tert-butyl nitrite - heterocyclization - tetranitromethaneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690053.
- Supporting Information
Primary Data
- Primary Data
for this article are available online at https://doi.org/10.1055/s-0039-1690053 and can be cited using the following DOI: 10.4125/pd0113th.
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For reviews and some recent examples, see:
For recent examples of various bioactive bis(heterocycles), see:
For review and recent examples, see: