Producción Científica Profesorado

Conformationalstudies of N-carbomethoxy-2-alkoxyindolenines by dynamic NMR, crystallography, and molecular mechanics

Suárez Castillo, Oscar Rodolfo


Conformational studies of N-carbomethoxy-2-alkoxyindolenines by dynamic NMR, crystallography, and molecular mechanics. Suárez-Castillo O. R., Contreras-Martínez Y. M. A., Beiza-Granados L., Meléndez-Rodríguez M., Villagómez-Ibarra J. R., Torrez-Valencia J. M., Morales-Ríos M. S., Joseph-Nathan P. DOI:


The synthesis of N-carbomethoxy-2-alkoxyindolenines and the transformation to their tautomeric indoles is reported. Variable-temperature 1H NMR studies of these 2-alkoxyindolenines evidenced dynamic processes involving two low-energy E and Z equilibrating conformers around the NC(O) carbamate bond, for which the barriers (?G?) between the two conformations are in the order of 12.513.9 kcal/mol, as deduced from computational NMR line shape simulations. The rotational barrier decreases as the bulkiness of the alkoxyl group increases, with the E conformer being always more stable. Molecular mechanics calculations evidenced a preferred quasi-axial position of the alkoxyl group in the five-membered ring as the steric effect increases, in agreement with X-ray diffraction studies.

Producto de Investigación

Artículos relacionados

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

Role of lipid peroxidation in biliary obstruction in the rat

Transesterifications mediated by t-BuNH2

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

Synthesis of Acetamido(indol-3-yl)propanol Derivatives

Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives

Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling

One-potsynthesis of conformationallyrestrictedspirooxindoles

Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine

Synthesis of ?4:?2-Exocyclic-Diene Iridium(I) Complexes Derived from 1,3-Oxazolidin-2-ones and Their...