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

✍ Scribed by Alan R. Katritzky; Martin A. C. Button; Sergey N. Denisenko

Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
505 KB
Volume
37
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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.

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