Producción Científica Profesorado

Dimethyldioxirane oxidation of N-substituted-2-methylindoles to indoxyls and bisindoxyls



Meléndez Rodríguez, Myriam

2013

Aristeo-Dominguez, A., Meléndez-Rodríguez, M., Suárez Castillo, O. R., Contreras-Martínez, Y. M. A., Suárez-Ramírez, L., Trejo-Carbajal, N., Morales-Ríos, M. S., Joseph-Nathan, P. (2013). Dimethyldioxirane oxidation of N-substituted-2-methylindoles to indoxyls and bisindoxyls. Heterocycles 87, 1249-1267.


Abstract


Oxidation of 2-methylindoles 12a-f with dimethyldioxirane (DMD) revealed that N-unprotected 12b,f and protected N-carbamate 2-methylindole 12c afforded indoxyls 16b,c and o-(N-propionyl)aminobenzoic acid 17f as the main products, while N-alkyl- or N-aryl-2-methylindoles 12a,d,e gave 1,5?-diphenyl-4?,5?-dihydro-3?H-spiro[indole-2,2?-pyrano[3,2-b]indol]-3(1H)-one (10), 2,3'-bisindolin-3-ones13, dispiro[indole-2,2?-furan-5?,2?-indole]diones 14 or 2-[(3-oxoindolin-2-yl)methyl]-2-hydroxyindolin-3-ones 15. The structure of dimers10, 13a,d,e, 14a,d and 15a,d followed from NMR measurements, X-ray diffraction analysis confirmed those structures of 13a,d,e,14a,d and 15d, and some mechanistic implications are discussed.



Producto de Investigación




Artículos relacionados

Photochemical rearrangements of highly functionalized longipinene derivatives

DFT and NMR parameterized conformation of valeranone

First Total Synthesis of ()-Flustraminol B

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

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

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

Cleavage of alkoxycarbonylprotectinggroups from carbamates by t-BuNH2

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii

Synthesis of Indolylindolines Mediated by tert-BuNH2

Transesterifications mediated by t-BuNH2