What question did this study set out to answer?

Develop a direct and efficient catalytic strategy to synthesize isoquinolone skeletons from allene precursors via intramolecular carbopalladation followed by amidation.

January 1, 2003HeterocyclesOpen Access

A Facile and Direct Synthesis of Isoquinolone Derivatives from Allenes: Intramolecular Carbopalladation of Allenes Followed by Amidations

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Authors

KHKunio HiroiOhu University KWKazuhiro WatanabeIHI Corporation (Czechia)

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Implication

Experimental synthesis demonstrates efficient formation of isoquinolone derivatives via palladium-catalyzed allene cyclization, indicating a direct route for heterocyclic scaffold construction.

Key Points

Develop a direct and efficient catalytic strategy to synthesize isoquinolone skeletons from allene precursors via intramolecular carbopalladation followed by amidation.
Subjected (o-iodobenzamidoalkyl)allene substrates to cyclization in the presence of a catalytic amount of palladium(II) acetate [Pd(OAc)2].
Mediated intramolecular carbopalladation followed by nucleophilic substitution to induce ring closure into isoquinolones.
Palladium-catalyzed cyclization of (o-iodobenzamidoalkyl)allene compounds successfully provided the corresponding isoquinolone derivatives in good yields.
Facilitated smooth heterocyclic core formation using 2-iodobenzamide derivatives, surmounting cyclization difficulties previously observed with 2-iodobenzylamine analogs.

Cite This Study

Hiroi et al. (2003) studied this question.

synapsesocial.com/papers/6aa4bc695b13064ba7dc3e5b https://doi.org/10.3987/com-02-s53

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Implication

Experimental synthesis demonstrates efficient formation of isoquinolone derivatives via palladium-catalyzed allene cyclization, indicating a direct route for heterocyclic scaffold construction.

A Facile and Direct Synthesis of Isoquinolone Derivatives from Allenes: Intramolecular Carbopalladation of Allenes Followed by Amidations

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Implication

Key Points

Cite This Study

A Facile and Direct Synthesis of Isoquinolone Derivatives from Allenes: Intramolecular Carbopalladation of Allenes Followed by Amidations

Discussion

Member takes

Implication

Key Points

Cite This Study

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