Ring opening of 2-substituted 4-nitrothiophenes with pyrrolidine. Access to new functionalized nitro-unsaturated building blocks was written by Dell’Erba, C.;Gabellini, A.;Novi, M.;Petrillo, G.;Tavani, C.;Cosimelli, B.;Spinelli, D.. And the article was included in Tetrahedron in 2001.Application of 42137-24-6 This article mentions the following:
The reaction conditions of the ring-opening processes of 3-nitrothiophene and of 3-nitrobenzo[b]thiophene with pyrrolidine and AgNO3 were optimized as well as those of the subsequent S-methylation of the ensuing Ag enethiolates to 4-methylthio-2-nitro-1-pyrrolidino-1,3-butadiene (I) and 1-(2-methylthiophenyl)-1-nitro-2-pyrrolidinoethylene (II). Under such conditions 2-substituted 4-nitrothiophenes consistently gave good yields of the corresponding 4-methylthio-2-nitro-1-pyrrolidino-4-R-1,3-butadienes (pyr-MNRB, R = PhS, PhSO2, MeS, MeSO2, MeCO, MeCO2, and CN). The nitroenamine derivatives I, II, and pyr-MNRB were then reacted with p-MeC6H4MgBr to furnish moderate to good yields of 4-methylthio-2-nitro-1-(p-tolyl)-4-R-1,3-butadienes (p-tolyl-MNRB) and 1-(2-methylthiophenyl)-1-nitro-2-(p-tolyl)ethylene(III). Stereochem. of the interesting building blocks I–III, pyr-MNRB, and p-tolyl-MNRB was assigned on the grounds of 1H NMR data and NOE experiments In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Application of 42137-24-6).
4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Application of 42137-24-6
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts