Divergent [4+3] Annulations of β′-Acetoxy Allenoates: Access to Azepino[1,2- <i>a</i> ]indole Derivatives

In this work, the Lewis base-catalyzed divergent [4 + 3] annulation reactions of β'-acetoxy allenoates with two different indole derivatives are reported. A wide range of azepino[1,2-<i>a</i>]indole derivatives was smoothly obtained from 2-((3-formyl-1<i>H</i>-indol-2-yl)methyl)malonates by employing the DABCO catalyst. The syntheses of two regioselective diazepino[1,2-<i>a</i>]indole derivatives from 3-formyl-1<i>H</i>-indole-2-carboxamides are realized by the catalysis of DABCO and organophosphine, respectively. A series of functional group transformations can be achieved in the three 1,2-fused seven-membered indole products.

Authors

Institutions

Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-10-14
DOI
https://doi.org/10.1021/acs.joc.5c01904
Citations
2
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
1.87
Controls
|||
ALL TIME
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
SEP
OCT
article

Divergent [4+3] Annulations of β′-Acetoxy Allenoates: Access to Azepino[1,2- a ]indole Derivatives

You Huang, Yannan Zhu
2 citations
The Journal of Organic Chemistry
Asymmetric Synthesis and Catalysis
1.87
article

Divergent [4+3] Annulations of β′-Acetoxy Allenoates: Access to Azepino[1,2- a ]indole Derivatives

You Huang, Yannan Zhu
article en
2 citations

Abstract

In this work, the Lewis base-catalyzed divergent [4 + 3] annulation reactions of β'-acetoxy allenoates with two different indole derivatives are reported. A wide range of azepino[1,2-<i>a</i>]indole derivatives was smoothly obtained from 2-((3-formyl-1<i>H</i>-indol-2-yl)methyl)malonates by employing the DABCO catalyst. The syntheses of two regioselective diazepino[1,2-<i>a</i>]indole derivatives from 3-formyl-1<i>H</i>-indole-2-carboxamides are realized by the catalysis of DABCO and organophosphine, respectively. A series of functional group transformations can be achieved in the three 1,2-fused seven-membered indole products.

The Journal of Organic ChemistryVol. 90(42)
Nankai University (CN), Institute of Organic Chemistry (HU), Yancheng Institute of Technology (CN)
Openalex Percentile: Top 13%
Asymmetric Synthesis and Catalysis
1.87
AI Navigator

Ask Laika to Summarize, Analyze, and Connect papers live on the map.

Summarize Papers & Methodologies

Extract key findings, datasets, and comparative methods across publications.

Benchmark Rankings & Visual Analytics

Rank top research institutions, authors, funders, topics, and journals by Field-Weighted Citation Impact (FWCI) and paper volume with instant charts.

Connect Distant Disciplines

Bridge topological clusters on the map to find hidden collaborative intersections.