Producción Científica Profesorado

Synthesis of Indolylindolines Mediated by tert-BuNH2



Meléndez Rodríguez, Myriam

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

Regioselective Synthesis of 3-Indolyl(alkoxy)acetates

First Total Synthesis of ()-Flustraminol B

Transesterifications mediated by t-BuNH2

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

DFT and NMR parameterized conformation of valeranone

Mechanisticstudies of the photochemicalrearrangement of 1-oxolongipin-2-ene derivatives

Photochemical rearrangements of highly functionalized longipinene derivatives

Quirogane, Prenopsane, and Patzcuarane Skeletons Obtained by Photochemically Induced Molecular Rearr...

Cleavage of alkoxycarbonylprotectinggroups from carbamates by t-BuNH2

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii