Producción Científica Profesorado

Synthesis of Indolylindolines Mediated by tert-BuNH2



Suárez Castillo, Oscar Rodolfo

2009

Suárez-Castillo Oscar R., Meléndez-Rodríguez Myriam, Morales-García Ana L., Cano-Escudero Indira C., Contreras-Martínez Yaneth M. A., Morales-Ríos Martha S., Joseph-Nathan Pedro . Synthesis of indolylindolines mediated by t-BuNH2 Heterocycles 78, 1463-1476 (2009). ISSN 0385-5414. DOI: 10.3987/COM-08-11627


Abstract


An improved synthesis of N1-carbomethoxylated indolylindolines 2 from 5-substituted indoles 1, by replacing the previously employed strong acids or toxic metals with t-BuNH2/MeOCOCl in CH2Cl2/H2O, is described. The substituent effect of electron donor or acceptor groups was examined, revealing that electron-deficient indoles are less reactive to dimerization than electron-rich indoles, with 5-cyano and 5-nitroindoles leading to no reaction. A dynamic process caused by the restricted rotation of the N-CO2Me bond of 2 was evidenced by 1H NMR measurements.



Producto de Investigación




Artículos relacionados

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

The absoluteconfiguration of cuauhtemone and related compounds

Regioselective Synthesis of 3-Indolyl(alkoxy)acetates

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

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii

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

Trapping enols of esters and lactones with diazomethane

One-potsynthesis of conformationallyrestrictedspirooxindoles

Synthesis of Indolylindolines Mediated by tert-BuNH2

Cascade [1,3]-Sigmatropic Rearrangements of Ketene O,O-Acetals: Kinetic and DFT Level Mechanistic St...