Song, Li-Rui published the artcileMetal-free hypervalent iodine-promoted tandem carbonyl migration and unactivated C(Ph)-C(Alkyl) bond cleavage for quinolone scaffold synthesis, HPLC of Formula: 118-90-1, the publication is Chemical Communications (Cambridge, United Kingdom) (2022), 58(60), 8340-8343, database is CAplus and MEDLINE.
An unexpected iodine(III)-mediated C(sp3)-C(sp2) bond cleavage of 3-(methylamino)-2-(2-substitutedbenzoyl)acrylates 2-R-3-R1-4- R2-5-R3C6HC(O)C(C(O)OEt)=CHNHR4 (R = H, Me, Ph, 2-(naphthalen-2-yl)ethyl, etc.; R1 = H, Me, OMe, NO2, etc.; R2 = H, Me, Br, NO2, etc.; R3 = H, Me; R4 = Et, Bn, Me, i-pr) for efficient synthesis of privileged scaffold 4-quinolones I was described. Notably, a wide range of alkyl groups (e.g. Me, tert-Bu or alkyl chain) can be conveniently cleaved in this system. The detailed mechanism studies revealed that the transformation proceeded through cascade ipso-cyclization and 1,2-carbonyl migration, and the smaller bond energy determined ortho C-C bond cleavage rather than C-H bond cleavage, via an enamine radical intermediate.
Chemical Communications (Cambridge, United Kingdom) published new progress about 118-90-1. 118-90-1 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Natural product, name is 2-Methylbenzoic acid, and the molecular formula is C12H15BBrFO2, HPLC of Formula: 118-90-1.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia