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1,3-Dipolar cycloaddition reaction of 4,5-dihydro-1H-imidazole 3-oxides with alkynes

✍ Scribed by Sergey A. Popov; Nikita V. Chukanov; Galina V. Romanenko; Tatjana V. Rybalova; Yuri V. Gatilov; Vladimir A. Reznikov

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
346 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

Dihydro-1H-imidazole 3-oxides bearing different substituents at positions 1 and 2 of the heterocycle were shown to react with a wide range of acceptor-substituted alkynes forming corrsponding cycloadductsderivatives of 1,2,3,7a-tetrahydroimidazo[1,2-b]isoxazole. High regioselectivity of this process stipulated by conjugation of the nitrogen atom with the nitrone group was revealed.

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1,3-Dipolar Cycloaddition or Nucleophili
1,3-Dipolar Cycloaddition or Nucleophilic Addition: Influence of Solvents and Nature of Substituents in the Reagent and Substrate Molecules on the Reaction of 4,5-Dihydro-1H-imidazole 3-Oxides with Alkynes.
✍ Sergey A. Popov; Vladimir A. Reznikov 📂 Article 📅 2006 🏛 John Wiley and Sons ⚖ 22 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

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Two competitive processes -1,3-dipolar cycloaddition and nucleophilic addition -in the reaction of 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole 3-oxides with asymmetrically substituted alkynes were shown to occur. The influence of solvents and the nature of substituents in the reagent and substrate

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**1,3‐Dipolare Cycloadditionen von Benzonitriloxiden an 1‐Aroyl‐4,5‐dihydro‐3,4,4‐trimethyl‐5‐methylen‐1__H__‐pyrazole** Die 1‐Aroyl‐4,5‐dihydro‐3,4,4‐trimethyl‐5‐methylen‐1__H__‐pyrazole **2**, dargestellt durch Wasserabspaltung aus den entsprechenden 4,5‐Dihydro‐5‐hydroxy‐1__H__‐pyrazolen **1**,

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## Abstract Benzonitrile oxide cycloadds to the CC bond of substituted 4,5‐dihydro‐3‐methylene‐2(3__H__)‐furanones 1a–1g. Thus, (__E__)‐1a and (__E__)‐1b are converted into the corresponding isoxazolinespirodihydrofuranones (4__RS__,5__RS__)‐2a and (4__RS__,5__RS__)‐2b, and (__E__)‐1c is converted

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## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v