Chemo, stereo, and regioselective addition of α‐(2‐methoxyaryl)‐<i>N</i>‐aryl nitrones to diarylidineacetone: Synthesis of novel isoxazolidines

Microwave-assisted stereoselective 1,3-dipolar cycloaddition of C,N-diarylnitrones (i.e., N-(arylmethylidene)benzenamine N-oxides) 2 to substituted bis(arylmethylidene)acetones (¼ 1,5-diarylpenta-1,4-dien-3-ones) 1 leading to diastereoisomer pairs of bis-isoxazolidines 3 and 4 in good to excellent yield is described (Scheme 2 and Table 2). The configuration outcome of the reaction is discussed based on the NMR and X-ray data of the products. The use of microwaves for carrying out organic reactions is a well established procedure and has emerged as a promising synthetic technique, since the reactions are clean, fast, and economical with easy workup. The technique of microwave irradiation enables organic reactions to occur expeditiously at ambient pressure and provides unique reaction processes with special attributes such as accelerated reaction rate and relatively good yields [1g] [2b] [6] with selectivity in certain cases.

show abstract

Synthesis and fungicidal activity of 2-(diphenylmethyl)-3-arylisoxazolidine-5-carboxamides

Żelechowski

Golebiewski

Krawczyk

2015

Monatsh Chem

View full text Add to dashboard Cite

Chemo, stereo, and regioselective addition of α‐(2‐methoxyaryl)‐N‐aryl nitrones to diarylidineacetone: Synthesis of novel isoxazolidines

Abstract: 1 2 3 4 5A new set of 2,3,4,5-tetrasubstituted isoxazolidines with an , -unsaturated carbonyl function at position 4 has been synthesized. The multicomponent approach and microwave irradiation protocol have also been investigated for the above synthesis.

Cited by 5 publications

References 25 publications

ChemInform Abstract: Chemo‐, Stereo‐, and Regioselective Addition of α‐(2‐Methoxyaryl)‐N‐aryl Nitrones to Diarylidineacetone: Synthesis of Novel Isoxazolidines.

ChemInform Abstract: Chemo‐, Stereo‐, and Regioselective Addition of α‐(2‐Methoxyaryl)‐N‐aryl Nitrones to Diarylidineacetone: Synthesis of Novel Isoxazolidines.

Microwave‐Assisted Stereoselective 1,3‐Dipolar Cycloaddition of C,N‐Diarylnitrone (i.e., N‐(Arylmethylidene)benzenamine N‐Oxide) and Bis(arylmethylidene)acetone (=1,5‐Diarylpenta‐1,4‐dien‐3‐one): NMR and Crystal Analysis of Diastereoisomeric Bis(isoxazolidines)

Synthesis and fungicidal activity of 2-(diphenylmethyl)-3-arylisoxazolidine-5-carboxamides

Contact Info

Product

Resources

About