A Practical, Ligand-Free, Palladium-Catalyzed Isocyanide Insertion Reaction for the Construction of Novel Ring-Fused Quinazolinones

Fei Ji; Mei-fang Lv; Wen-bin Yi; Chun Cai

doi:10.1055/s-0033-1338936

Synthesis, Table of Contents

Synthesis 2013; 45(14): 1965-1974
DOI: 10.1055/s-0033-1338936

paper

A Practical, Ligand-Free, Palladium-Catalyzed Isocyanide Insertion Reaction for the Construction of Novel Ring-Fused Quinazolinones

Fei Ji

Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China Fax: +86(25)84315030 Email: c.cai@mail.njust.edu.cn

,

Mei-fang Lv

Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China Fax: +86(25)84315030 Email: c.cai@mail.njust.edu.cn

,

Wen-bin Yi

Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China Fax: +86(25)84315030 Email: c.cai@mail.njust.edu.cn

,

Chun Cai*

Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China Fax: +86(25)84315030 Email: c.cai@mail.njust.edu.cn

› Author Affiliations

Abstract

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Abstract

A high-yielding, ligand-free, palladium-catalyzed isocyanide insertion reaction for the synthesis of phthalazino[1,2-b]quinazolinones from the readily obtainable quinazolinones has been developed. Easily handled and relatively low-cost palladium(II) acetate was used as the catalyst, without an additional ligand. Preparation of the quinazolinones involved the cascade reaction of isatoic anhydrides, phenylhydrazines and 2-bromobenzaldehyde catalyzed by p-toluenesulfonic acid in one pot. This novel protocol may be applicable for the synthesis of other important ring-fused heterocyclic compounds.

Key words

ligand-free - palladium catalysis - isocyanide insertion reaction - ring-fused quinazolinones - depropargylation

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References

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