Synthesis and Transformation into 4,5-Dihydroisoxazole Derivatives of Methyl(hetarylalkyl)-N-allyl-N-phenylcarbamates

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Abstract

By alkylation of aromatic carbamates with allyl bromide under liquid-liquid phase transfer catalysis, the corresponding N-allyl derivatives of aryl carbamates were obtained in 63–71% yields. It has been established that the cycloaddition of arene carbonitrile N-oxides, generated in situ from the corresponding oximes in the presence of chloramine T, to the allylic fragment upon boiling in ethanol leads to the production of the corresponding 4,5-dihydroisoxazole derivatives in 89–96% yields.

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About the authors

A. V. Velikorodov

Astrakhan Tatishchev State University; Astrakhan State Medical University

Author for correspondence.
Email: avelikorodov@mail.ru
ORCID iD: 0000-0001-9802-8252
Russian Federation, pl. Shahumyana, 1, Astrakhan, 414000; ul. Bakinskaya, 121, Astrakhan, 414000

E. N. Kutlalieva

Astrakhan Tatishchev State University; Astrakhan State Medical University

Email: avelikorodov@mail.ru
ORCID iD: 0000-0002-9712-4223
Russian Federation, pl. Shahumyana, 1, Astrakhan, 414000; ul. Bakinskaya, 121, Astrakhan, 414000

N. V. Zolotareva

Astrakhan Tatishchev State University

Email: avelikorodov@mail.ru
ORCID iD: 0000-0002-3209-2929
Russian Federation, pl. Shahumyana, 1, Astrakhan, 414000

N. N. Stepkina

Astrakhan Tatishchev State University

Email: avelikorodov@mail.ru
ORCID iD: 0000-0001-8603-3951
Russian Federation, pl. Shahumyana, 1, Astrakhan, 414000

S. B. Nosachev

Astrakhan Tatishchev State University

Email: avelikorodov@mail.ru
ORCID iD: 0000-0001-8469-5425
Russian Federation, pl. Shahumyana, 1, Astrakhan, 414000

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Supplementary files

Supplementary Files
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1. JATS XML
2. Scheme 1 1a–h, 2a–h: R = Me, R' = H (a); R = Me, R' = 4-Meo (b); R = Me, R' = 4-MeO (c); R = Me, R' = 4-NO2 (d); R = Me, R' = 4-Br(e); R = 2-furylmethyl, R' = H(f), R= 2-morpholinoethyl, R' = H(g); R = 2-(pyridine-2-Yl)ethyl (I).

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3. Scheme 2 2a–f, 3a–f: R = Me, R' = H, Ar = 3-NO2C6H4 (a); R = Me, R' = H, Ar = 3,4-OCH2OC6H3 (b); R = Me, R' = 4-Me, Ar = 4-BrC6H4 (c); R = Me, R' = 4-MeO, Ar = 4-MeOC6H4 (d); R = 2-furanmethyl, R' = H, AR = 4-meoc6h4 (E); R = 2-Furanmethyl, R' = H, AR = 3-No2c6h4 (F); R = me, R' = 4-NO2, AR = 4-Meoc6h4 (G)

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