A concise route to indoloazocines via a sequential Ugi–gold-catalyzed intramolecular hydroarylation

Modha, Sachin G.; Vachhani, Dipakkumar; Jacobs, Jeroen; Meervelt, Luc Van; Eycken, Erik V. Van der

doi:10.1039/c2cc32586a

Cited by 93 publications

(47 citation statements)

References 54 publications

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“…45 The protocol involved mild reaction conditions, found incompatible. Later, an improved version of this protocol was reported 46 where Au(PPh 3 )SbF 6 is used instead of the previously described Au(PPh 3 )OTf.…”

Section: Transition Metal-catalyzed Carbocyclizationsmentioning

confidence: 99%

Metal-mediated post-Ugi transformations for the construction of diverse heterocyclic scaffolds

et al. 2015

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The Ugi-4CR is by far one of the most successful multicomponent reactions leading to high structural diversity and molecular complexity. However, the reaction mostly affords a linear peptide backbone, enabling post-Ugi transformations as the only solution to rigidify the Ugi-adduct into more drug like species. Not surprisingly, the development of these transformations, leading to new structural frameworks, has expanded rapidly over the last few years. As expected, palladium-catalyzed reactions have received the foremost attention, yet other metals, particularly gold complexes, are fast catching up. This tutorial review outlines the developments achieved in the past decade, highlighting the modifications that are performed in a sequential or domino fashion with emphasis on major concepts, synthetic applications of the derived products as well as mechanistic aspects.

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Section: Transition Metal-catalyzed Carbocyclizationsmentioning

confidence: 99%

Metal-mediated post-Ugi transformations for the construction of diverse heterocyclic scaffolds

et al. 2015

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“…This synthetic sequence is atom economic and mild conditions are applied to generate a very complex molecular structure from readily available starting materials. Based on this work and our continuous interest in transition metal catalysis [45–54], multicomponent reactions [55–57] and the chemistry of the indole core [58–60], we herein report a post-Ugi gold-catalyzed intramolecular domino cyclization sequence for the synthesis of spiroindolines with propargylamines as an alkyne source (Scheme 1). …”

Section: Introductionmentioning

confidence: 99%

Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines

Kumar¹,

Vachhani²,

Modha³

et al. 2013

Beilstein J. Org. Chem.

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SummaryAn Ugi four-component reaction of propargylamine with 3-formylindole and various acids and isonitriles produces adducts which are subjected to a cationic gold-catalyzed diastereoselective domino cyclization to furnish diversely substituted spiroindolines. All the reactions run via an exo-dig attack in the hydroarylation step followed by an intramolecular diastereoselective trapping of the imminium ion. The whole sequence is atom economic and the application of a multicomponent reaction assures diversity.

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“…In this regard, goldcatalyzed reactions of alkyne-functionalized indoles allow the construction of a wide range of heteropolycyclic frameworks. [23][24][25][26][27][28][29][30][31][32][33] However, related cycloisomerizations of indoles with a tethered allene have been less studied. [34][35][36] In particular, a gold-catalyzed hydroarylation of N-allenylmethylindoles that furnishes dihydro-pyrido[1,2-a]-1H-indoles has been described (Scheme 1a).…”

Section: Figure 1 Naturally Occurring 49-dihydro-1h-carbazolesmentioning

confidence: 99%

Regioselective Synthesis of Elusive 4,9-Dihydro-1H-Carbazoles by Gold-Catalyzed Cycloisomerization of 3-Allenylmethylindoles

et al. 2013

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Abstract.A general and efficient synthesis of 4,9-dihydro-1H-carbazoles from 3-allenylmethylindoles is reported. The process, catalyzed by a cationic gold(I) complex, involves a formal C2H bond activation of the indole unit by reaction with allenes. The nature of the substituents at the allylic as well as the terminal position of the allene moiety has a crucial effect on the regioselectivity of the cyclization, which is also influenced by the catalyst and the solvent employed. Moreover, some evidence of the 2 contribution of different reaction routes is provided which led us to propose a plausible multi-pathway mechanism consistent with all the results described.

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A concise route to indoloazocines via a sequential Ugi–gold-catalyzed intramolecular hydroarylation

Abstract: A diversity oriented approach for the synthesis of indoloazocines is reported employing an Ugi reaction followed by a gold-catalyzed intramolecular hydroarylation.

Cited by 93 publications

References 54 publications

Metal-mediated post-Ugi transformations for the construction of diverse heterocyclic scaffolds

Metal-mediated post-Ugi transformations for the construction of diverse heterocyclic scaffolds

Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines

Regioselective Synthesis of Elusive 4,9-Dihydro-1H-Carbazoles by Gold-Catalyzed Cycloisomerization of 3-Allenylmethylindoles

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