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Literature DB >> 19256518

A concise and versatile synthesis of viridicatin alkaloids from cyanoacetanilides.

Abstract

The efficient synthesis of 3-hydroxy-4-arylquinolin-2(1H)-ones through one-pot Knoevenagel condensation/epoxidation of cyanoacetanilides followed by decyanative epoxide-arene cyclization is described. A convergent assembly with functionalized aldehydes allows for rapid synthesis with diverse substitution patterns. Isolation of 3-hydroxy-4-arylquinolin-2(1H)-ones is readily accomplished by precipitation and filtration.

Entities: Chemical

Mesh：

Substances：

Year: 2009 PMID： 19256518 DOI： 10.1021/ol900255g

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

9 in total

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A concise and versatile synthesis of viridicatin alkaloids from cyanoacetanilides.

1. Synthesis and SAR studies of dual AKT/NF-κB inhibitors against melanoma.

2. In Vitro Evaluation of the Photoprotective Potential of Quinolinic Alkaloids Isolated from the Antarctic Marine Fungus Penicillium echinulatum for Topical Use.

3. Harnessing the Substrate Promiscuity of Dioxygenase AsqJ and Developing Efficient Chemoenzymatic Synthesis for Quinolones.

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