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.
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
Cleavage of alkoxycarbonylprotectinggroups from carbamates by t-BuNH2
Synthesis of Bromoindole Alkaloids from Laurencia brongniartii