Producción Científica Profesorado

Mechanistic study of reversible solid-state melt isomerization of 2-oxindoles to 2-quinolinones and its occurrence in a mass spectrometer



Suárez Castillo, Oscar Rodolfo

2019

Gelacio Martínez-Gudiño, Nadia A.Pérez-Rojas, Joel J.Trujillo-Serrato, Yolanda Mora-Pérez, Oscar R.Suárez-Castillo, Martha S.Morales-Ríos, Journal of Molecular Structure, 1175 (2019) 828-835 doi:10.1016/j.molstruc.2018.08.056


Abstract


An eco-friendly equilibrated rearrangement of a series of 2-oxo-3-indolyl acetic acids (1) with 2-oxo-1,2,3,4-tetrahydroquinoline-4-carboxylic acid derivatives (2) was investigated through a solid state melt reaction (SSMR). Mechanistic insight into the thermal rearrangement is provided by 13C-isotopic labeling. The standard mass spectra of 1 and 2 were virtually identical preventing their reliable identification. Reversible interconversion of 1 and 2 was evidenced to occur in the inlet system of a mass spectrometer under electron impact conditions. Relative abundances of fragment ions were found to be a function of temperature.



Producto de Investigación




Artículos relacionados

Reactivity of TpMe2Ir(C2H4)(DMAD) with carboxylic acids. A DFT study on geometrical isomers and stru...

Regioselective Synthesis of 3-Indolyl(alkoxy)acetates

Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea

Configuration, stereodynamics and crystal structure of 3-substituted-2-oxofuro[2,3-b]indoles

Role of lipid peroxidation in biliary obstruction in the rat

The absoluteconfiguration of cuauhtemone and related compounds

13C NMR and crystallographic evidence of push-pull effects in furoindolic ?-enamino esters

Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2

Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural ...

Synthesis of Indolylindolines Mediated by tert-BuNH2