Producción Científica Profesorado

Synthesis and characterization of azathiaethers macrocyclic ringsdecorated with one or two 2-pyridylmethyl fragments

Mendoza Espinosa, Daniel


Simplicio González-Montiel, René Velázquez-Jiménez , Diego Martínez-Otero, Daniel Mendoza-Espinosa, J. Manuel Vásquez-Pérez, Noemí Andrade-López, Julián Cruz-Borbolla, Oscar Muñoz-Granados, Journal of Molecular Structure 1176 (2019) 54-65 doi:10.1016/j.molstruc.2018.08.060


Monoaza-dithia- (1a e 3a) and diaza-tetrathia- (1b and 3b) macrocycles with a pendant 2-pyridylmethylfragment have been prepared by the reaction between 2-(aminomethyl)pyridine with dibromidedithioetherderivatives. Four of the macrocycles have been characterized by X-ray crystallography,revealing the formation of two 14- and 15-membered monoaza-dithiaethers, and two 26- and 30-membered diaza-tetrathiaether macrocycles featuring one or two exo-2-pyridylmethyl fragments,respectively. The monoaza-dithiaethers macrorings adopt a twisted conformation while the diazatetrathiaethersmacrorings display a rectangular conformation. Intramolecular interactions of macrorings2a, 3a, 1b and 3b were studied by non-covalent interaction analysis. It was found that smallermacrorings are less stable than larger ones due to larger strain energies and that intramoleculardispersive interactions and hydrogen bonding play an important role in the macrocycle conformationadopted.

Producto de Investigación

Artículos relacionados

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

Transesterifications mediated by t-BuNH2

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

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

Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor

Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine

Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii

Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters

Regioselective Synthesis of 3-Indolyl(alkoxy)acetates