Chen, Zhen published the artcileTransition-Metal-Free [3 + 2] Cycloaddition of Nitroolefins and Diazoacetonitrile: A Facile Access to Multisubstituted Cyanopyrazoles, Synthetic Route of 5153-73-1, the publication is Organic Letters (2018), 20(7), 2120-2124, database is CAplus and MEDLINE.
Nitroalkenes such as β-nitrostyrenes (E)-RCH:CHNO2 [R = Ph, 4-MeC6H4, 4-MeOC6H4, 4-Me2NC6H4, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-F3CC6H4, 4-NCC6H4, 3-MeOC6H4, 2-MeOC6H4, 2-BrC6H4, 1-naphthyl, 2-naphthyl, 9-anthracenyl, 2-furyl, 2-thienyl, (E)-R1CH:CH, PhCC, PhCH2CH2, Bu, i-Bu, cyclohexyl; R1 = Ph, 4-MeOC6H4, 2-O2NC6H4] underwent metal-free regioselective [3+2]-cycloaddition reactions with diazoacetonitrile N2:CHCN either used sep. or generated in situ from aminoacetonitrile hydrochloride with Cs2CO3 in THF to give 3-pyrazolecarbonitriles such as I [R = Ph, 4-MeC6H4, 4-MeOC6H4, 4-Me2NC6H4, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-F3CC6H4, 4-NCC6H4, 3-MeOC6H4, 2-MeOC6H4, 2-BrC6H4, 1-naphthyl, 2-naphthyl, 9-anthracenyl, 2-furyl, 2-thienyl, (E)-R1CH:CH, PhCC, PhCH2CH2, Bu, i-Bu, cyclohexyl; R1 = Ph, 4-MeOC6H4, 2-O2NC6H4] in 55-93% yields. The cycloaddition reaction was also performed in tandem with regioselective N-alkylation reactions with MeI or PhCH2Br to yield 1-methyl- or 1-benzyl-3-pyrazolecarbonitriles in 31-73% yields with 10-48% of the 2-alkyl-3-pyrazolecarbonitrile regioisomers (<25% yields in ten of twelve cases). Diazoacetonitrile is potentially explosive and should be handled with caution.
Organic Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Synthetic Route of 5153-73-1.
Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts