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Paper | Regular issue | Vol 87, No. 6, 2013, pp.1249-1267
Published online, 2nd May, 2013
DOI: 10.3987/COM-13-12669
Dimethyldioxirane Oxidation of N-Substituted-2-methylindoles to Indoxyls and Bisindoxyls

Alberto Aristeo-Dominguez, Myriam Meléndez-Rodríguez,* Oscar R. Suárez Castillo,* Yaneth M. A. Contreras-Martínez, Lizbeth Suárez-Ramírez, Nayely Trejo-Carbajal, Martha S. Morales-Ríos, and Pedro Joseph-Nathan

*Área Académica de Química, Universidad Autónoma del Estado de Hidalgo, Mineral de la Reforma, Hidalgo, 42184, Mexico


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-ones 13, 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 dimers 10, 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.