Synthesis of 5-(chlorodinitromethyl)-2-methyl-2H-tetrazole and its reaction with diazoalkanes

Autor:	M. A. Abdel’rakhim, A. G. Tyrkov
Rok vydání:	2013
Předmět:	chemistry.chemical_classification chemistry.chemical_compound chemistry Diazomethane Potassium Organic Chemistry chemistry.chemical_element Azole Salt (chemistry) Diazo Tetrazole Reactivity (chemistry) Medicinal chemistry
Zdroj:	Russian Journal of Organic Chemistry. 49:632-634
ISSN:	1608-3393 1070-4280
DOI:	10.1134/s1070428013040271
Popis:	It is known that 5-dinitromethyl-2-methyl-2H-tetrazole (I) reacts with diazomethane to give isomeric methyl (2-methyltetrazol-5-yl)nitromethanenitronates and (1,3-dimethyl-1H-tetrazol-5-yl)dinitromethylide [1]. With a view to study how the nature of substituted 5-dinitromethyltetrazoles affects the direction of their reactions with diazo compounds, we have synthesized an analog of tetrazole (I), 5-(chlorodinitromethyl)-2methyl-2H-tetrazole (II), and examined its reactions with diazomethane (III) and diazoethane (IV). Tetrazole (II) was prepared in 70% yield by chlorination of azole I potassium salt (Scheme 1). tion of C–O bond, yielding nitronic acid esters as primary O-alkylation products. These esters react with excess diazoalkane, thus being converted in succession into substituted ethenes and then cyclic esters, dihydroisoxazole N-oxides VI and VIII (Scheme 2). The product ratio is likely to be determined by higher reactivity of the ambident anion in the O-alkylation process.
Databáze:	OpenAIRE
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