Direct Access to Cinnoline-4-carbaldehydes: Iridium(III)-Catalyzed C–H [4 + 2] Annulation Using 2-Chloromalonaldehyde as a C ₂ Synthon

Chao Zhang; Guanyu Qiao; Lin Dong

doi:10.1021/acs.joc.6c00331

May 6, 2026The Journal of Organic Chemistry

Direct Access to Cinnoline-4-carbaldehydes: Iridium(III)-Catalyzed C–H [4 + 2] Annulation Using 2-Chloromalonaldehyde as a C ₂ Synthon

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Key Points

The aim is to establish a method for synthesizing cinnoline-4-carbaldehyde derivatives through metal-catalyzed reactions.
Utilized iridium(III) as a catalyst for C–H annulation.
Employed 2-chloromalonaldehyde as a C2 synthon.
Executed a dephthaloylation step for functionalization.
Successfully synthesized cinnoline-4-carbaldehyde derivatives with high efficiency.
Facilitated direct installation of aldehyde groups for further functionalization.

Implication

Demonstrates efficient synthesis of cinnoline-4-carbaldehyde derivatives, implying improved synthetic applications.

Abstract

synthon in metal-catalyzed cyclization reactions; (ii) the direct and efficient installation of an aldehyde group, a versatile synthetic handle and reactive motif enabling subsequent functionalization; and (iii) a subsequent dephthaloylation step that affords synthetically valuable cinnoline-4-carbaldehyde derivatives.

Discussion

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Cite This Study

Zhang et al. (2026) studied this question.

synapsesocial.com/papers/69fd7e5cbfa21ec5bbf068bf https://doi.org/10.1021/acs.joc.6c00331

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Direct Access to Cinnoline-4-carbaldehydes: Iridium(III)-Catalyzed C–H [4 + 2] Annulation Using 2-Chloromalonaldehyde as a C ₂ Synthon

Key Points

Implication

Abstract

Discussion

Cite This Study

Direct Access to Cinnoline-4-carbaldehydes: Iridium(III)-Catalyzed C–H [4 + 2] Annulation Using 2-Chloromalonaldehyde as a C ₂ Synthon

Key Points

Implication

Abstract

Discussion

Cite This Study

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