1,3-Dipolar Cycloaddition Reactions of Indan-1-one Enamines across Arylnitrile Oxides Leading to Novel Cyclic Isoxazoline Derivatives

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Titre1,3-Dipolar Cycloaddition Reactions of Indan-1-one Enamines across Arylnitrile Oxides Leading to Novel Cyclic Isoxazoline Derivatives
Type de publicationJournal Article
Year of Publication2014
AuteursJelizi H, Wannassi N, Rammah MEl Baker, Ciamala K, Knorr M, Rousselin Y, Kubicki MM, Strohmann C, Enescu M
JournalJOURNAL OF HETEROCYCLIC CHEMISTRY
Volume51
Pagination383-391
Date PublishedMAR
Type of ArticleArticle
ISSN0022-152X
Résumé

Synthesis of a series of cyclic fused-isoxazolines has been accomplished by regioselective and diastereoselective 1,3-dipolar cycloaddition of 3-methylindan-1-one enamines (1a, 1b, 1c) and 3-phenylindan-1-one enamines (2a, 2b, 2c) to arylnitrile oxides (3d, 3e, 3f, 3g, 3h). The structure of the cycloadducts was elucidated by H-1 and C-13 NMR spectroscopy. The proposed regio- and stereochemistry of fused-compounds (4) and (5) has also been corroborated by two single-crystal X-ray diffraction studies carried out on 4-methyl-8b-morpholinyl-3-(p-tolyl)-4H-3a,8b-dihydroindeno[2,3-d]isoxa zoline (4be) and 3-(p-anisyl)-4-phenyl-8b-pyrrolidinyl-4H-3a,8b-dihydroindeno[2,3-d]iso xazoline (5af) and by means of density functional theory calculations.

DOI10.1002/jhet.1588