【摘 要】
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The indole framework is a privileged core structure of natural products and material chemistry and these important organics are most likely derived from the ind
【机 构】
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SchoolofChemistryandChemicalEngineering,SouthChinaUniversityofTechnology,Guangzhou,510640
【出 处】
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第五届岭南有机化学论坛暨华南理工大学-兰州大学有机化学双边论坛
论文部分内容阅读
The indole framework is a privileged core structure of natural products and material chemistry and these important organics are most likely derived from the indole C2-H alkenylation/cyclization cascade.Schipper,Yoshikai,Kanai and our group successively reported that N-substituted N,N-dimethylaminocarbonyl,pyridyl or pyrimidyl group from indoles could efficiently enhance intermolecular C2-alkenylation with alkynes(Scheme 1a).1.2 We recently attempted to employ N-alkylaminocarbonyl as a directing group to produce C2-alkenylated indole intermediates C through the reductive cross-coupling with alkynes B,and followed by intramolecular carboamination and oxidation to construct HPIOs(D),but we finally only obtained the unexpected(Z)-alkenylated indole E(Scheme 1b).2b In this communication,we tried to switch the alkyne coupling partner(B) to the α-acyl diazo compound(F),and envisioned that carboamido group could assist the formation of metallocyclic intermediate G through a transition metal-catalyzed C-H activation,intermolecular carbenoid insertion into indole C2-H bond and metal carbene migratory insertion process,then underwent an intramolecualr cyclization reaction to furnish 2H-pyrimido[1,6-a]indol-1-ones(D)(Scheme 1c).
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