Synthesis of Azocine-Fused Indoles via Gold(I)-Catalyzed Cyclization of Azido-alkynes

Herein, we report a gold(I)-catalyzed cascade cyclization of azido-alkynes bearing an enol ester moiety, leading to indole-fused eight-membered rings. This method allows for the one-step construction of indole and tetrahydroazocin-4-one via an α-imino gold carbene intermediate. The resulting scaffold would be useful for accessing natural products with an eight-membered ring-fused indole moiety.

Authors

Hiroaki Ohno (ORCID: https://orcid.org/0000-0002-3246-4809)
Daiki Hasegawa
Atsuhito Tsuji
Norihito Arichi (ORCID: https://orcid.org/0000-0003-3618-4959)
Luca C. Greiner (ORCID: https://orcid.org/0000-0002-6235-407X)
Shinsuke Inuki (ORCID: https://orcid.org/0000-0002-7525-1280)

Institutions

Kyoto University (JP)

Publication Details

Journal: The Journal of Organic Chemistry
Published: 2024-12-31
DOI: https://doi.org/10.1021/acs.joc.4c02704
Citations: 7
Primary Topic: Catalytic Alkyne Reactions
Type: article
Field-Weighted Citation Impact: 1.75

Funders

Uehara Memorial Foundation
Japan Agency for Medical Research and Development
Japan Society for the Promotion of Science

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article

Synthesis of Azocine-Fused Indoles via Gold(I)-Catalyzed Cyclization of Azido-alkynes

Hiroaki Ohno, Daiki Hasegawa, Atsuhito Tsuji, Norihito Arichi et al.

Dec 31, 2024

7 citations

The Journal of Organic Chemistry

Catalytic Alkyne Reactions

1.75

article

Synthesis of Azocine-Fused Indoles via Gold(I)-Catalyzed Cyclization of Azido-alkynes

Hiroaki Ohno, Daiki Hasegawa, Atsuhito Tsuji, Norihito Arichi, Luca C. Greiner, Shinsuke Inuki

December 31, 2024article en

7 citations

Abstract

Herein, we report a gold(I)-catalyzed cascade cyclization of azido-alkynes bearing an enol ester moiety, leading to indole-fused eight-membered rings. This method allows for the one-step construction of indole and tetrahydroazocin-4-one via an α-imino gold carbene intermediate. The resulting scaffold would be useful for accessing natural products with an eight-membered ring-fused indole moiety.

The Journal of Organic ChemistryVol. 90(1)

Kyoto University (JP)

Uehara Memorial Foundation, Japan Agency for Medical Research and Development, Japan Society for the Promotion of Science

Openalex Percentile: Top 16%

Catalytic Alkyne Reactions

1.75

DOI Source OpenAlex

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Synthesis of Azocine-Fused Indoles via Gold(I)-Catalyzed Cyclization of Azido-alkynes — Hiroaki Ohno, Daiki Hasegawa, et al. · The Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS