143378-19-2Relevant academic research and scientific papers
Uncommon 1,2-migration of a nitro group within a β-nitrostyryl moiety: Synthetic scope and mechanistic details
Bianchi, Lara,Ghelfi, Franco,Giorgi, Gianluca,Maccagno, Massimo,Petrillo, Giovanni,Spinelli, Domenico,Stenta, Marco,Tavani, Cinzia
, p. 6298 - 6309 (2013/10/21)
The unusual migration of a nitro group from the β- to the α-position of a β-aryl-α-nitroethenyl moiety, following a nitrocyclopropane to isoxazoline N-oxide isomerization, has been studied from a mechanistic and synthetic points of view. As a result, two series of isomeric isoxazoline N-oxides could be obtained under controlled conditions. When reacted with diazomethane, a model transposed isoxazoline cleanly furnished a new, interesting pyrazolylisoxazole. Copyright
Synthetic exploitation of the ring-opening of 3,4-dinitrothiophene. Access to 1,4-disubstituted 2,3-dinitro-1,3-butadienes and 2,3-diaminobutanes
Dell'Erba, Carlo,Novi, Marino,Petrillo, Giovanni,Spinelli, Domenico,Tavani, Cinzia
, p. 3313 - 3326 (2007/10/03)
The reactions of 1,4-bis(diethylamino)-2,3-dinitro-1,3-butadiene 1 (deriving from ring-opening of 3,4-dinitrothiophene with diethylamine) with one mole of Grignard reagents give, together with disubstituted products 1,4-dialkyl- and 1,4-diaryl-2,3-dinitro-1,3-butadienes 2, the monosubstituted 1-alkyl-4-diethylamino- and 1-aryl-4-diethyl-amino-2,3-dinitro-1,3-butadienes 8 in yields dependent on the nature of the reagent employed. Aryl-substituted compounds 8 undergo a highly regioselective reaction with aryl Grignard reagents to furnish good yields of 1-Ar1-4-Ar2-2,3-dinitro-1,3-butadienes 9. Preliminary results are also reported on the transformation of some dinitrobutadienes 2 and 9 into the corresponding 1,4-disubstituted 2,3-diaminobutanes 10.
Synthetic exploitation of the ring-opening of 3,4-dinitrothiophene. Access to 1,4-disubstituted 2,3-dinitro-1,3-butadienes and 2,3-butanedione dioximes
Dell'Erba, Carlo,Mele, Andrea,Novi, Marino,Petrillo, Giovanni,Stagnaro, Paola
, p. 4407 - 4418 (2007/10/02)
The optimized ring-opening reaction of 3,4-dinitrothiophene 1 with either primary or secondary amines leads to 1,4-bis(alkylamino)- and 1,4-bis(arylamino)- 2 or 1,4-bis(dialkylamino)-2,3-dinitro-1,3-butadienes 3 in satisfactory to excellent yields. While
