Heterocyclization of gem -dichlorocyclopropanes: 'Fine tuning' of reactivity towards nitronium triflate

Autor:	Elena B. Averina, Victor B. Rybakov, Kseniya N. Sedenkova, Vladimir I. Minkin, Tamara S. Kuznetsova, Dmitry A. Vasilenko, D. V. Steglenko, Yuri K. Grishin, Nikolay S. Zefirov, Julia V. Kolodyazhnaya
Rok vydání:	2017
Předmět:	Solvent 010405 organic chemistry Chemistry Organic Chemistry Drug Discovery Anhydrous Organic chemistry Reactivity (chemistry) 010402 general chemistry 01 natural sciences Biochemistry Trifluoromethanesulfonate 0104 chemical sciences
Zdroj:	Tetrahedron Letters. 58:2955-2958
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2017.06.047
Popis:	The heterocyclization of gem-dichlorocyclopropanes upon treatment with nitronium triflate in organic nitriles was studied and the influence of the medium on the reaction pathway was shown. While in anhydrous solvent 5-chloroisoxazole was the only product, the admixture with water promoted a three-component heterocyclization affording 4-chloropyrimidine N-oxides. This phenomenon was rationalized using DFT calculations.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::98de3e72672557eb84733a81b1d39565 https://doi.org/10.1016/j.tetlet.2017.06.047 Zobrazit plný text záznamu Full Text from ScienceDirect