Sequential [3 + 2] Annulation/Intramolecular Transesterification of o -Hydroxyaryl Azomethines and Conjugated Dienes: Access to Chromeno[4,3- b ]pyrrolidines

Zhenjie Gan; Ganyi Fan; Jiachen Jiang; Tong Sun; Er-Qing Li

doi:10.1021/acs.joc.5c02375

February 11, 2026The Journal of Organic Chemistry

Sequential [3 + 2] Annulation/Intramolecular Transesterification of o -Hydroxyaryl Azomethines and Conjugated Dienes: Access to Chromeno[4,3- b ]pyrrolidines

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Key Points

To explore a new cyclization reaction that efficiently constructs chromeno[4,3-b]pyrrolidine derivatives using o-hydroxyaryl azomethines and conjugated dienes.
Conducted a domino cyclization reaction of o-hydroxyaryl azomethines with electron-deficient conjugated dienes.
Investigated the chemoselectivity and substrate scope of the reaction.
Demonstrated the scalability of the reaction under standard conditions.
The method successfully produces chromeno[4,3-b]pyrrolidine derivatives with excellent chemoselectivity.
The reaction is effective across a broad range of substrates.
Reaction parameters allow for scaling up to gram quantities.

Implication

This research demonstrates a novel method to construct chromeno[4,3-b]pyrrolidine derivatives, implying potential applications in organic synthesis.

Abstract

Herein, we report a domino cyclization reaction of o-hydroxyaryl azomethines with electron-deficient conjugated dienes. This method provides a novel and efficient pathway for the construction of chromeno[4,3-b]pyrrolidine derivatives. The protocol exhibits excellent chemoselectivity and a broad substrate scope. Furthermore, the reaction can be scaled up to gram quantities under the standard conditions.

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Cite This Study

Gan et al. (2026) studied this question.

synapsesocial.com/papers/699011932ccff479cfe58553 https://doi.org/10.1021/acs.joc.5c02375

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Sequential [3 + 2] Annulation/Intramolecular Transesterification of o -Hydroxyaryl Azomethines and Conjugated Dienes: Access to Chromeno[4,3- b ]pyrrolidines

Key Points

Implication

Abstract

Discussion

Cite This Study

Sequential [3 + 2] Annulation/Intramolecular Transesterification of o -Hydroxyaryl Azomethines and Conjugated Dienes: Access to Chromeno[4,3- b ]pyrrolidines

Key Points

Implication

Abstract

Discussion

Cite This Study

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