DIMETHYLDIOXIRANE OXIDATION OF N-SUBSTITUTED-2-METHYLINDOLES TO INDOXYLS AND BISINDOXYLS

作者：Aristeo Dominguez Alberto^*; Melendez Rodriguez Myriam; Suarez Castillo Oscar R; Contreras Martinez Yaneth M A; Suarez Ramirez Lizbeth; Trejo Carbajal Nayely; Morales Rios Martha S; Joseph Nathan Pedro

来源：Heterocycles, 2013, 87(6): 1249-1267.

DOI：10.3987/COM-13-12669

• Dimethyldioxirane
• Indoxyl
• Spiroindoxyl
• Bisindoxyl
• Dialkylindigo

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.

• 出版日期2013-6-1