Lewis-Acid-Catalyzed Decarboxylative Annulation of 2‑Aminoindole-3-Carboxylate with Ynals Involving [3 + 2] Spirocycloaddition and 2,3-Aza Migration

Lewis-Acid-Catalyzed Decarboxylative Annulation of 2‑Aminoindole-3-Carboxylate with Ynals Involving [3 + 2] Spirocycloaddition and 2,3-Aza Migration

2-Aminoindole-3-carboxylates undergo a Lewis-acid-catalyzed decarboxylative annulation with ynals to afford dihydrochromeno-fused δ-carbolines through a 2,3-aza migration, via a spirocyclic intermediate generated from an initial [3 + 2] spirocycloaddition. Brønsted acid interference changes the path...

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Veröffentlicht in:Organic letters 2020-02, Vol.22 (3), p.1117-1123
Hauptverfasser: Rajesh, Manda, Kumar, Ravi, Puri, Surendra, Nanubolu, Jagadeesh Babu, Reddy, Maddi Sridhar
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container_end_page 1123
container_issue 3
container_start_page 1117
container_title Organic letters
container_volume 22
creator Rajesh, Manda
Kumar, Ravi
Puri, Surendra
Nanubolu, Jagadeesh Babu
Reddy, Maddi Sridhar
description 2-Aminoindole-3-carboxylates undergo a Lewis-acid-catalyzed decarboxylative annulation with ynals to afford dihydrochromeno-fused δ-carbolines through a 2,3-aza migration, via a spirocyclic intermediate generated from an initial [3 + 2] spirocycloaddition. Brønsted acid interference changes the path from a [3 + 2] to a [4 + 2] addition. 2-Aminoindoles without an ester functional group at C3 underwent a different condensation, followed by hetero-Diels–Alder reaction to generate chromeno-fused α-carbolines.
doi_str_mv 10.1021/acs.orglett.9b04626
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title Lewis-Acid-Catalyzed Decarboxylative Annulation of 2‑Aminoindole-3-Carboxylate with Ynals Involving [3 + 2] Spirocycloaddition and 2,3-Aza Migration
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