By means of an iodide-catalyzed nitrocyclopropane to 4,5-dihydroisoxazoline 2-oxide isomerization, the 1,1'-dinitro-[1,1']bi(cyclopropyl)s I (Ar = 4-MeC6H4, 1-naphthyl, 2-thienyl), derived from an initial ring-opening of 3,4-dinitrothiophene, can be stereospecifically converted into the bisnitronates II (same Ar). From these, successive N-oxide redn. [P(OMe)3/dioxane] and aromatization (DDQ/toluene) provide convenient access to the interesting 4,5,4'5'-tetrahydro[3,3']biisoxazolyls III and [3,3']biisoxazolyls IV, respectively.
Access to 5,5’-diaryl substituted 4,5,4’,5’-tetrahydro[3,3’]biisoxazolyl 2,2’-dioxides, 4,5,4’,5’-tetrahydro[3,3’]biisoxazolyls and [3,3’]biisoxazolyls via an initial ring-opening of 3,4-dinitrothiophene / L., Bianchi; C., Dell'Erba; Gasparrini, Francesco; M., Novi; G., Petrillo; F., Sancassan; C., Tavani. - In: ARKIVOC. - ISSN 1551-7004. - ELETTRONICO. - --:(2002), pp. 142-158. [10.3998/ark.5550190.0003.b14]
Access to 5,5’-diaryl substituted 4,5,4’,5’-tetrahydro[3,3’]biisoxazolyl 2,2’-dioxides, 4,5,4’,5’-tetrahydro[3,3’]biisoxazolyls and [3,3’]biisoxazolyls via an initial ring-opening of 3,4-dinitrothiophene
GASPARRINI, Francesco;
2002
Abstract
By means of an iodide-catalyzed nitrocyclopropane to 4,5-dihydroisoxazoline 2-oxide isomerization, the 1,1'-dinitro-[1,1']bi(cyclopropyl)s I (Ar = 4-MeC6H4, 1-naphthyl, 2-thienyl), derived from an initial ring-opening of 3,4-dinitrothiophene, can be stereospecifically converted into the bisnitronates II (same Ar). From these, successive N-oxide redn. [P(OMe)3/dioxane] and aromatization (DDQ/toluene) provide convenient access to the interesting 4,5,4'5'-tetrahydro[3,3']biisoxazolyls III and [3,3']biisoxazolyls IV, respectively.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
