1, 3‐Dipolar Cycloaddition Reactions of Indan‐1‐one Enamines across Arylnitrile Oxides Leading to Novel Cyclic Isoxazoline Derivatives. (18th November 2013)

• Record Type: Journal Article
• Authors: Jelizi, Hanene; Wannassi, Nadia; El Baker Rammah, Mohamed; Ciamala, Kabula; Knorr, Michael; Rousselin, Yoann; Kubicki, Marek M.; Strohmann, Carsten; Enescu, Mironel
• Is Part Of: Journal of heterocyclic chemistry. Volume 51:Number 2(2014)
• Page Start: 383
• Page End: 391
• Publication Date: 2013-11-18
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.1588
• Languages: English
• ISSNs: 0022-152X

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>Synthesis of a series of cyclic fused‐isoxazolines has been accomplished by <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">regioselective</named-content> and <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">diastereoselective</named-content><named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">1, 3‐dipolar cycloaddition</named-content> of 3‐methylindan‐1‐one enamines (<bold>1a</bold>, <bold>1b</bold>, <bold>1c</bold>) and 3‐phenylindan‐1‐one enamines (<bold>2a</bold>, <bold>2b</bold>, <bold>2c</bold>) to arylnitrile oxides (<bold>3d</bold>, <bold>3e</bold>, <bold>3f</bold>, <bold>3g</bold>, <bold>3h</bold>). The structure of the cycloadducts was elucidated by <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy. The proposed regio‐ and stereochemistry of fused‐compounds (<bold>4</bold>) and (<bold>5</bold>) has also been corroborated by two single‐crystal X‐ray diffraction studies carried out on 4‐methyl‐8b‐morpholinyl‐3‐(<italic>p</italic>‐tolyl)‐4<italic>H</italic>‐3a, 8b‐dihydroindeno[2, 3‐d]isoxazoline (<bold>4be</bold>) and 3‐(<italic>p</italic>‐anisyl)‐4‐phenyl‐8b‐pyrrolidinyl‐4<italic>H</italic>‐3a, 8b‐dihydroindeno[2, 3‐d]isoxazoline (<bold>5af</bold>) and by means of density functional theory calculations.</p> </abstract>