(4+3) annulation of enone-tethered indoles with α-alkylidene succinimides: access to seven-membered azepino[3,2,1-<i>hi</i>]indole scaffolds

We have developed a straightforward synthesis of azepino[3,2,1-<i>hi</i>]indole architectures with four contiguous chiral carbons as single diastereomers. This metal-free protocol between indole-enones and alkylidene succinimides proceeds efficiently under ambient conditions, demonstrating a broad scope in good to excellent yields. The feasibility of the current methodology was illustrated by one-pot, gram-scale synthesis and further modifications.

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Publication Details

Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc02885j
Citations
3
Primary Topic
Chemical synthesis and alkaloids
Type
article
Field-Weighted Citation Impact
2.81
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article

(4+3) annulation of enone-tethered indoles with α-alkylidene succinimides: access to seven-membered azepino[3,2,1-hi]indole scaffolds

Rama Krishna Peddinti, Km Roshani, Mohammad Saim Raza
3 citations
Chemical Communications
Chemical synthesis and alkaloids
2.81
article

(4+3) annulation of enone-tethered indoles with α-alkylidene succinimides: access to seven-membered azepino[3,2,1-hi]indole scaffolds

Rama Krishna Peddinti, Km Roshani, Mohammad Saim Raza
article en
3 citations

Abstract

We have developed a straightforward synthesis of azepino[3,2,1-<i>hi</i>]indole architectures with four contiguous chiral carbons as single diastereomers. This metal-free protocol between indole-enones and alkylidene succinimides proceeds efficiently under ambient conditions, demonstrating a broad scope in good to excellent yields. The feasibility of the current methodology was illustrated by one-pot, gram-scale synthesis and further modifications.

Chemical CommunicationsVol. 61(67)
Indian Institute of Technology Roorkee (IN)
Openalex Percentile: Top 10%
Chemical synthesis and alkaloids
2.81
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