Temperature-Dependent, Switchable Synthesis of α-Carbolines and Tetrahydropyrrolo[2,3-b]indoles via Formal [4 + 1 + 1] and [3 + 1 + 1] Cyclizations

A switchable one-pot, three-component cyclization of 3-vinylindoles, sulfonyl azides, and α-bromoketones has been developed for the synthesis of α-carbolines and tetrahydropyrrolo[2,3-b]indoles. The advantages of this strategy include excellent product selectivity, good functional group tolerance, highly functionalized products, and mild conditions.

Authors

Siyang Xing (ORCID: https://orcid.org/0000-0002-6240-0363)
Fangli Jing (ORCID: https://orcid.org/0000-0001-6029-7481)
Long Yi Jin (ORCID: https://orcid.org/0000-0002-3104-8424)
Bolin Zhu (ORCID: https://orcid.org/0000-0002-6846-566X)
Xiqing Wang (ORCID: https://orcid.org/0000-0002-6520-6814)
Ji Pang

Institutions

Tianjin Normal University (CN)

Publication Details

Journal: The Journal of Organic Chemistry
Published: 2025-05-30
DOI: https://doi.org/10.1021/acs.joc.5c00683
Citations: 4
Primary Topic: Asymmetric Synthesis and Catalysis
Type: article
Field-Weighted Citation Impact: 3.74

Funders

National Natural Science Foundation of China
Natural Science Foundation of Tianjin City

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article

Temperature-Dependent, Switchable Synthesis of α-Carbolines and Tetrahydropyrrolo[2,3-b]indoles via Formal [4 + 1 + 1] and [3 + 1 + 1] Cyclizations

Siyang Xing, Fangli Jing, Long Yi Jin, Bolin Zhu et al.

May 30, 2025

4 citations

The Journal of Organic Chemistry

Asymmetric Synthesis and Catalysis

3.74

article

Temperature-Dependent, Switchable Synthesis of α-Carbolines and Tetrahydropyrrolo[2,3-b]indoles via Formal [4 + 1 + 1] and [3 + 1 + 1] Cyclizations

Siyang Xing, Fangli Jing, Long Yi Jin, Bolin Zhu, Xiqing Wang, Ji Pang

May 30, 2025article en

4 citations

Abstract

A switchable one-pot, three-component cyclization of 3-vinylindoles, sulfonyl azides, and α-bromoketones has been developed for the synthesis of α-carbolines and tetrahydropyrrolo[2,3-b]indoles. The advantages of this strategy include excellent product selectivity, good functional group tolerance, highly functionalized products, and mild conditions.

The Journal of Organic ChemistryVol. 90(23)

Tianjin Normal University (CN)

National Natural Science Foundation of China, Natural Science Foundation of Tianjin City

Openalex Percentile: Top 7%

Asymmetric Synthesis and Catalysis

3.74

DOI Source OpenAlex

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Temperature-Dependent, Switchable Synthesis of α-Carbolines and Tetrahydropyrrolo[2,3-b]indoles via Formal [4 + 1 + 1] and [3 + 1 + 1] Cyclizations — Siyang Xing, Fangli Jing, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS