- Exploiting Iminoquinones as Electrophilic at Nitrogen "n+" Synthons for C-N Bond Construction
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New methods for C-N bond construction exploiting the N-centered electrophilic character of iminoquinones are reported. Iminoquinones, generated in situ via the condensation of o-vinylanilines with benzoquinones, undergo acid-catalyzed cyclization to afford N-arylindoles in excellent yields. Under similar reaction conditions, homoallylic amines react analogously to afford N-arylpyrroles. Additionally, organometallic nucleophiles are shown to add to the nitrogen atom of N-alkyliminoquinones to provide amine products. Finally, iminoquinones are shown to be competent electrophiles for copper-catalyzed hydroamination.
- Mori-Quiroz, Luis M.,Comadoll, Chelsea G.,Super, Jonathan E.,Clift, Michael D.
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supporting information
p. 7008 - 7013
(2021/09/18)
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- A cascade approach to 3D cyclic carbamates: Via an ionic decarboxylative functionalization of olefinic oxamic acids
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An m-CPBA-mediated intramolecular epoxidation-decarboxylative alkoxylation cascade reaction of olefinic oxamic acids has been developed. The distinct ionic decarboxylative mechanism was preliminarily revealed. The protocol features mild reaction conditions and operational simplicity, allowing the construction of diverse medicinally valuable 5-7 membered 3D cyclic carbamate architectures in moderate to high yields.
- Fan, Huaqiang,Wan, Yi,Pan, Peng,Cai, Wenbin,Liu, Shihui,Liu, Chuanxu,Zhang, Yongqiang
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- Deoxygenation Reactions of ortho-Nitrostyrenes with Carbon Monoxide Catalysed by Metal Carbonyls: a New Route to Indoles
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The metal carbonyls Fe(CO)5, Ru3(CO)12, and Rh6(CO)16 are catalysts for the deoxygenation of ortho-nitrostyrenes under carbon monoxide pressure to give indole derivatives; the crystal structure of a non-catalytically active rhodium complex obtained during the synthesis of (5e) is reported.
- Crotti, Corrado,Cenini, Sergio,Rindone, Bruno,Tollari, Stefano,Demartin, Francesco
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p. 784 - 786
(2007/10/02)
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