An Unexpected Transition-Metal Free Regioselective Cyclization of Alkynyl-Tethered Indoles to Prepare Indole-Fused Azepino[2,1-b]quinazolinones and Spiroindole-pyrrolo[2,1-b]quinazolinones

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This is a Experimental Study study.

Pei‐Sen Zou; Yong Geng; Xiaoqing Liu; Jun‐Cheng Su; Cheng‐Xue Pan; Dong‐Liang Mo; Gui‐Fa Su

doi:10.1039/d5gc04267d

January 1, 2025Green Chemistry

An Unexpected Transition-Metal Free Regioselective Cyclization of Alkynyl-Tethered Indoles to Prepare Indole-Fused Azepino[2,1-b]quinazolinones and Spiroindole-pyrrolo[2,1-b]quinazolinones

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Key Points

Efficiently synthesizing indole-fused azepino[2,1-b]quinazolinones shows great potential for drug development.
The cyclization achieved good to excellent yields, showcasing a promising alternative to transition-metal catalysis.
The regioselective nature of the cyclization permits the creation of new spiroindole-pyrrolo[2,1-b]quinazolinones with targeted properties.
This base-promoted approach under mild reaction conditions opens new avenues for future synthetic methodologies.

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Implication

The method demonstrates base-promoted cyclization of alkynyl-indoles to yield quinazolinones, implying new pathways for synthesis.

Abstract

We report an unexpectedly transition-metal free and base-promoted regioselective cyclization of N3-alkynyl-2-indolylquinazolinones for the efficient synthesis of various indole-fused azepino[2,1-b]quinazolinones and spiroindole-pyrrolo[2,1-b]quinazolinones in good to excellent yields under mild reaction...

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Zou et al. (2025) studied this question.

synapsesocial.com/papers/68e9b1c1ba7d64b6fc132448 https://doi.org/10.1039/d5gc04267d

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An Unexpected Transition-Metal Free Regioselective Cyclization of Alkynyl-Tethered Indoles to Prepare Indole-Fused Azepino[2,1-b]quinazolinones and Spiroindole-pyrrolo[2,1-b]quinazolinones

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An Unexpected Transition-Metal Free Regioselective Cyclization of Alkynyl-Tethered Indoles to Prepare Indole-Fused Azepino[2,1-b]quinazolinones and Spiroindole-pyrrolo[2,1-b]quinazolinones

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