Abstract. A new approach to useful precursors for the synthesis of isoxazolidine-carbocyclic nucleosides is detailed, starting from the readily available N-benzoyl-2,3-oxazanorborn-5-ene and introducing more polar and hydrophilic functionalities through 1,3-dipolar cycloaddition of carbethoxyformonitrile oxide, generated either from the corresponding hydroximoyl chloride a condensed carbethoxyisoxazoline nucleus. This polycyclic heterocycle is obtained or, more conveniently, by catalyzed condensation with ethyl nitroacetate.
Conversion of a nitrosocarbonyl hetero Diels-Alder cycloadduct to useful isoxazoline-carbocyclic aminols / P. Quadrelli; B. Bovio; A. Piccinini; P. Caramella; F. De Sarlo; F. Machetti. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 65:(2009), pp. 10679-10684.
Conversion of a nitrosocarbonyl hetero Diels-Alder cycloadduct to useful isoxazoline-carbocyclic aminols
DE SARLO, FRANCESCO;MACHETTI, FABRIZIO
2009
Abstract
Abstract. A new approach to useful precursors for the synthesis of isoxazolidine-carbocyclic nucleosides is detailed, starting from the readily available N-benzoyl-2,3-oxazanorborn-5-ene and introducing more polar and hydrophilic functionalities through 1,3-dipolar cycloaddition of carbethoxyformonitrile oxide, generated either from the corresponding hydroximoyl chloride a condensed carbethoxyisoxazoline nucleus. This polycyclic heterocycle is obtained or, more conveniently, by catalyzed condensation with ethyl nitroacetate.
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