Abstract:[reaction: see text] 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 beta-carbolin-1-one mimic of pancratistatin. Methyl 2-indolecarboxylat… Show more
“…After the preliminary studies in the 1960s and 1970s on the use of stoichiometric amounts of Lewis acids such as AlCl 3 , SnCl 4 , and BF 3 ,119 the discovery over the last decade of unusual Lewis acids such as lanthanide triflates120a and indium(III) salts120b–d opened up access to the catalytic ring‐opening of epoxides with indoles. Moreover, high pressures120e and silica gel120f were found to assist the regioselective C3‐alkylation of indoles with both racemic and enantiomerically pure epoxides.…”
Section: Reaction With C(sp3)‐based Alkylating Agentsmentioning
140 years ago Adolf von Baeyer proposed the structure of a heteroaromatic compound which revolutionized organic and medical chemistry: indole. After more than a century, indole itself and the complexity of naturally occurring indole derivatives continue to inspire and influence developments in synthetic chemistry. In particular, the ubiquitous presence of indole rings in pharmaceuticals, agrochemicals, and functional materials are testament to the ever increasing interest in the design of mild and efficient synthetic routes to functionalized indole derivatives. This Review emphasizes the achievements in the selective catalytic functionalization of indoles (C-C bond-forming processes) over the last four years.
“…After the preliminary studies in the 1960s and 1970s on the use of stoichiometric amounts of Lewis acids such as AlCl 3 , SnCl 4 , and BF 3 ,119 the discovery over the last decade of unusual Lewis acids such as lanthanide triflates120a and indium(III) salts120b–d opened up access to the catalytic ring‐opening of epoxides with indoles. Moreover, high pressures120e and silica gel120f were found to assist the regioselective C3‐alkylation of indoles with both racemic and enantiomerically pure epoxides.…”
Section: Reaction With C(sp3)‐based Alkylating Agentsmentioning
140 years ago Adolf von Baeyer proposed the structure of a heteroaromatic compound which revolutionized organic and medical chemistry: indole. After more than a century, indole itself and the complexity of naturally occurring indole derivatives continue to inspire and influence developments in synthetic chemistry. In particular, the ubiquitous presence of indole rings in pharmaceuticals, agrochemicals, and functional materials are testament to the ever increasing interest in the design of mild and efficient synthetic routes to functionalized indole derivatives. This Review emphasizes the achievements in the selective catalytic functionalization of indoles (C-C bond-forming processes) over the last four years.
“…addition of indoles to oxiranes and aziridines derived from cyclohexadiene diols) (255)(256)(257)(258). Analogues of narciclasine (68), pan crastistatin, and 7-deoxypancratistatin have been synthesized using modifications of the reported procedures as well as new methodologies (e.g.…”
“…The interesting bioisosteric replacement of the methylenedioxybenzene ring with the indole moiety as in compound 2 , also prepared by Hudlicky and coworkers, leads to essentially complete loss of in vitro anticancer activity. 29,30 …”
Section: Introduction and Biomedical Significancementioning
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