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Synthesis 2013; 45(14): 1965-1974
DOI: 10.1055/s-0033-1338936
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© Georg Thieme Verlag Stuttgart · New York

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
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Publication History

Received: 04 March 2013

Accepted after revision: 17 April 2013

Publication Date:
14 May 2013 (online)

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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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    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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Primary Data

    for this article are available online at http­://www.thieme-connect.com/ejournals/toc/synthesis and can be cited using the following DOI: 10.4125/pd0046th
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