Synthesis of Pyrroloquinones via a CAN Mediated Oxidative Free Radical Reaction of 1,3-Dicarbonyl Compounds with Aminoquinones
Joint Authors
Murugesan, Srinivasan
Xu, Su
Velu, Sadanandan
Nguyen, Thao
Kim, Sanghun
Dutta, Shilpa
Nadkarni, Dwayaja
Source
Issue
Vol. 2013, Issue 2013 (31 Dec. 2013), pp.1-12, 12 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2013-09-09
Country of Publication
Egypt
No. of Pages
12
Main Subjects
Abstract EN
Pyrroloquinone ring systems are important structural units present in many biologically active molecules including a number of marine alkaloids.
For example, they are found in a series of marine metabolites, such as tsitsikammamines, zyzzyanones, wakayin, and terreusinone.
Several of these alkaloids have exhibited antimicrobial, antimalarial, antifungal, antitumor, and photoprotecting activities.
Synthesis of pyrroloquinone unit is the key step in the synthesis of many of these important organic molecules.
Here, we present a ceric (IV) ammonium nitrate (CAN) mediated oxidative free radical cyclization reaction of 1,3-dicarbonyl compounds with aminoquinones as a facile methodology for making various substituted pyrroloquinones.
1,3-dicarbonyl compounds used in this study are ethyl acetoacetate, acetylacetone, benzoyl acetone, and N,N-dimethyl acetoacetamide.
The aminoquinones used in this study are 2-(benzylamino)naphthalene-1,4-dione and 6-(benzylamino)-1-tosyl-1H-indole-4,7-dione.
The yields of the synthesized pyrroloquinones ranged from 23–91%.
American Psychological Association (APA)
Nguyen, Thao& Nadkarni, Dwayaja& Dutta, Shilpa& Xu, Su& Kim, Sanghun& Murugesan, Srinivasan…[et al.]. 2013. Synthesis of Pyrroloquinones via a CAN Mediated Oxidative Free Radical Reaction of 1,3-Dicarbonyl Compounds with Aminoquinones. Journal of Chemistry،Vol. 2013, no. 2013, pp.1-12.
https://search.emarefa.net/detail/BIM-458469
Modern Language Association (MLA)
Nguyen, Thao…[et al.]. Synthesis of Pyrroloquinones via a CAN Mediated Oxidative Free Radical Reaction of 1,3-Dicarbonyl Compounds with Aminoquinones. Journal of Chemistry No. 2013 (2013), pp.1-12.
https://search.emarefa.net/detail/BIM-458469
American Medical Association (AMA)
Nguyen, Thao& Nadkarni, Dwayaja& Dutta, Shilpa& Xu, Su& Kim, Sanghun& Murugesan, Srinivasan…[et al.]. Synthesis of Pyrroloquinones via a CAN Mediated Oxidative Free Radical Reaction of 1,3-Dicarbonyl Compounds with Aminoquinones. Journal of Chemistry. 2013. Vol. 2013, no. 2013, pp.1-12.
https://search.emarefa.net/detail/BIM-458469
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-458469