ChemInform Abstract: Synthesis of Dihydropyrans and Dihydrofurans via Radical Cyclization of Unsaturated Alcohols and 1,3-Dicarbonyl Compounds

ChemInform ◽  
2014 ◽  
Vol 45 (44) ◽  
pp. no-no
Author(s):  
Hakan Aslan ◽  
Deniz E. Akpinar ◽  
Atilla Oektemer ◽  
Mehtap Yakut ◽  
Oguzhan Alagoez
Keyword(s):  
Radical Cyclization ◽  
Dicarbonyl Compounds ◽  
Unsaturated Alcohols

Iron-catalyzed tandem cyclization of olefinic dicarbonyl compounds with benzylic Csp3–H bonds for the synthesis of dihydrofurans

2015 ◽  
Vol 51 (23) ◽  
pp. 4803-4806 ◽  
Author(s):  
Li-Na Guo ◽  
Shun Wang ◽  
Xin-Hua Duan ◽  
Shi-Liu Zhou
Keyword(s):  
Radical Cyclization ◽  
Quaternary Carbon ◽  
Dicarbonyl Compounds ◽  
Ready Access ◽  
Tandem Cyclization

A novel iron-catalyzed radical cyclization of olefinic dicarbonyl compounds with benzyl hydrocarbons and simple alkanes has been developed. This protocol provides ready access to a variety of dihydrofurans containing a quaternary carbon center in moderate to good yields.

Tandem SN2′ nucleophilic substitution/oxidative radical cyclization of aryl substituted allylic alcohols with 1,3-dicarbonyl compounds

2017 ◽  
Vol 15 (15) ◽  
pp. 3239-3247 ◽  
Author(s):  
Zhen Zhang ◽  
Cheng Li ◽  
Shao-Hua Wang ◽  
Fu-Min Zhang ◽  
Xue Han ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Radical Cyclization ◽  
Allylic Alcohols ◽  
Dicarbonyl Compounds ◽  
Oxidative Radical Cyclization

Herein we present a novel tandem SN2′ nucleophilic substitution/oxidative radical cyclization of aryl substituted allylic alcohols with 1,3-dicarbonyl compounds.

scholarly journals Synthesis of Pyrroloquinones via a CAN Mediated Oxidative Free Radical Reaction of 1,3-Dicarbonyl Compounds with Aminoquinones

2013 ◽  
Vol 2013 ◽  
pp. 1-12 ◽  
Author(s):  
Thao Nguyen ◽  
Dwayaja Nadkarni ◽  
Shilpa Dutta ◽  
Su Xu ◽  
Sanghun Kim ◽  
...  
Keyword(s):  
Free Radical ◽  
Organic Molecules ◽  
Radical Reaction ◽  
Radical Cyclization ◽  
Biologically Active ◽  
Free Radical Reaction ◽  
Marine Alkaloids ◽  
Structural Units ◽  
Dicarbonyl Compounds ◽  
Marine Metabolites

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, andN,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%.

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