Efficient synthesis of 3,5-functionalized isoxazoles and isoxazolinesvia1,3-dipolar cycloaddition reactions of 1-propargyl- and 1-allylbenzotriazoles

Autor:	Martin A. C. Button, Alan R. Katritzky, Sergey N. Denisenko
Rok vydání:	2000
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Benzotriazole chemistry Organic Chemistry Propargyl 1 3-Dipolar cycloaddition Moiety Halide Nitrite Medicinal chemistry Alkyl
Zdroj:	Journal of Heterocyclic Chemistry. 37:1505-1510
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570370616
Popis:	3-Aryl-5-(benzotriazol-1-ylmethyl)- 10a-f and 3-p-methoxyphenyl-5-(α-benzotriazol-1-yl-α-ethoxymethyl)-isoxazole (13) were prepared in high yields by 1,3-dipolar cycloadditions of 1-propargyl-benzotriazole (5) and (α-ethoxypropargyl)benzotriazole (8), respectively, with nitrite oxides 3a-f (prepared in situ from benzohydroximoyl chlorides 2a-f). The benzotriazol-1-ylmethyl moiety was further elaborated by sequential lithiation and reaction with aldehydes, alkyl halides and Michael acceptors. Similar 1,3-cycloadditions using 1-allylbenzotriazole (6) and 1-(α-ethoxyallyl)benzotriazole (7) afforded 3,5-substituted isoxazolines 11b, f and 12 in excellent yields.
Databáze:	OpenAIRE
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