One-Pot, Highly Regioselective 1,3-Dipole Cycloaddition Promoted by Montmorillonite for the Synthesis of Spiro[indole-pyrrolizine], Spiro[indole-indolizine], and Spiro[indole-pyrrolidine] gem-Bisphosphonates

Abstract Various spiro[indole-pyrrolizine], spiro[indole-indolizine], and spiro[indole-pyrrolidine] gem -bisphosphonates were prepared by multicomponent reactions between isatins, tetraethyl vinylidenebis(phosphonate), and amino acids in the presence of montmorillonite. The one-pot reactions proceed...

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Veröffentlicht in:Synthesis (Stuttgart) 2015-12, Vol.47 (23), p.3783-3796
Hauptverfasser: Li, Guozhu, Wu, Mingshu, Liu, Fengjiao, Jiang, Jie
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract Various spiro[indole-pyrrolizine], spiro[indole-indolizine], and spiro[indole-pyrrolidine] gem -bisphosphonates were prepared by multicomponent reactions between isatins, tetraethyl vinylidenebis(phosphonate), and amino acids in the presence of montmorillonite. The one-pot reactions proceeded by 1,3-dipole cycloadditions of azomethine ylides formed in a decarboxylative manner. The proposed mechanism is in line with experimental data that confirmed that the azomethine ylide is formed in a decarboxylative manner; this provides new insight into the underlying mechanisms of such cycloadditions. The method has many notable features, such as a broad substrate scope, high efficiency, and high regioselectivity.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0035-1560463