@article{5f9ecc4c15a64f30ba4d82ac556f5d1c,
title = "Reactions of indole derivatives with oxiranes and aziridines on silica. Synthesis of β-carbolin-1-one mimic of pancratistatin: Journal of Organic Chemistry",
abstract = "(Chemical Equation Presented) Indole and several indoles functionalized at C-2 were condensed with oxiranes, vinyloxiranes, aziridines, and vinylaziridines in the solid state on the surface of silica. The yields of these reactions were compared to those obtained from Lewis acid-catalyzed ring-opening reactions performed in solution and found to be superior in each case. The solid-phase aziridine opening constituted a key step in the synthesis of the β-carbolin-1-one mimic of pancratistatin. Methyl 2-indolecarboxylate was found to react on the silica gel surface with N-tosylvinylaziridine in 68% yield. A nine-step synthesis of the pancratistatin mimic has been attained. The additional key transformation in this synthesis involved silica gel-catalyzed opening of an epoxide and hydrolysis of an acetonide. Detailed experimental procedures and full characterization are reported for all new compounds. {\textcopyright} 2005 American Chemical Society.",
keywords = "Amaryllidaceae Alkaloids, Aziridines, Carbolines, Combinatorial Chemistry Techniques, Ethylene Oxide, Indoles, Isoquinolines, Molecular Mimicry, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Plants, Medicinal, Silicon Dioxide, Catalysis, Derivatives, Hydrolysis, Reaction kinetics, Silica gel, Surfaces, 1 iodo hexahydro 2,3 dimethylbenzodioxol [3 indolyl] toluenesulfonamide, 1,2 epoxy 3 butene, 12c hexahydro 1,2 epoxy 3,4 benzodioxolylindolyl[2,3 c] 6 quinolinone, 12c hexahydro 1,2,3,4 tetraacetateindolyl [2,3 c] 6 quinolinone, 2 (indol 3 yl) 2,2 dimethyl 3a,4,5,7a tetrahydrobenzo[1,3]dioxol 4 ol, 2 (indol 3 yl)cyclohex 3 enol, 2 methyl [3 (2,2 dimethyl 3a,4,5,7a tetrahydrobenzo[1,3]dioxolyl) 4 tosylamine] 3 indolylacetate, 2 methyl [3 (2,2 dimethyl 3a,4,5,7a tetrahydrobenzo[1,3]dioxolyl) 4 tosylamine] 3 indolylcarboxylate, 3 indolyl 2 [3 (2,2 dimethyl 3a,4,5,7a tetrahydrobenzo[1,3]dioxolyl) 4 tosylamine]carboxylic acid, 3 indolyl 3 (2,2 dimethyl 3a,4,5,7a tetrahydrobenzo[1,3]dioxolel) 4 methylcarbamate, 3 indolyl 3 (2,2 dimethyl 3a,4,5,7a tetrahydrobenzo[1,3]dioxolyl) 4 tosylamine, 5 (2 carboxyindol 3 yl) 2,2 dimethyl 3a,4,5,6a tetrahydrobenzo[1,3]dioxol 4 tosylamine, aziridine, aziridine derivative, beta carboline 1 one, beta carboline derivative, carboxylic acid derivative, epoxide, ethylene oxide, indole derivative, isoquinoline derivative, Lewis acid, methyl 2 indolecarboxylate, n [2 (1,3 benzodioxol 5 yl) 3,4 dihydroxy 5,6 (isopropylidenedioxy)cyclohex 1 yl] 5 toluenesulfonamide 3 indolyl 2 methyl ester, n [2 (indol 3 yl)cyclohex 3 enyl] 4 methylbenzenesulfonamide, n [2 (indol 3 yl)cyclohexyl] 4 methylbenzenesulfonamide, n tosylvinylaziridine, silica gel, silicon dioxide, unclassified drug, vinylaziridine, article, catalysis, chemical structure, hydrolysis, quantum yield, solid, synthesis, Acetonides, Epoxides, Oxiranes, Nitrogen compounds",
author = "T. Hudlicky and U. Rinner and K.J. Finn and I. Ghiviriga",
note = "Export Date: 13 June 2023; Cited By: 76; Correspondence Address: T. Hudlicky; Department of Chemistry, Brock University, St. Catharines, Ont. L2S 3A1, Canada; email:
[email protected]; CODEN: JOCEA",
year = "2005",
month = apr,
day = "29",
doi = "10.1021/jo040292c",
language = "English",
volume = "70",
pages = "3490--3499",
journal = "J. Org. Chem.",
issn = "0022-3263",
number = "9",
}
