ChemInform Abstract: Lithium-Halogen Exchange-Initiated Cyclization Reactions. Part 3. Intramolecular Conjugate Addition Reactions of Unsaturated Acylphosphoranes.

ChemInform ◽  
1987 ◽  
Vol 18 (39) ◽  
Author(s):  
M. P. JUN. COOKE ◽  
R. K. WIDENER
Keyword(s):  
Conjugate Addition ◽  
Addition Reactions ◽  
Cyclization Reactions ◽  
Halogen Exchange

scholarly journals Programmed Sequential Additions to Halogenated Mucononitriles

2020 ◽  
Author(s):  
Adam Zahara ◽  
Elsa Hinds ◽  
Andrew Nguyen ◽  
Sidney Wilkerson-Hill
Keyword(s):  
Natural Product ◽  
Intramolecular Cyclization ◽  
Conjugate Addition ◽  
Secondary Amines ◽  
Addition Reactions ◽  
Cyclization Reactions ◽  
Carbon Nucleophiles ◽  
Multicomponent Coupling

Dihalomucononitriles were synthesized and their reactivity evaluated to assess their ability to function as linchpin reagents. Bis(2-chloroacrylonitrile) and bis(2-bromoacrylonitrile) were synthesized from 2,13-benzothiadiazole and shown to undergo conjugate addition reactions with both nitrogen (40–95% yield) and carbon nucleophiles (72–93% yield). Secondary amines were found to undergo monoadditions while carbon nucleophiles added twice. The sequence of addition of the nucleophiles could be controlled giving mixed addition products. The multicomponent coupling products could then be converted to natural product-like motifs using intramolecular cyclization reactions.

scholarly journals Programmed Sequential Additions to Halogenated Mucononitriles

2020 ◽  
Author(s):  
Adam Zahara ◽  
Elsa Hinds ◽  
Andrew Nguyen ◽  
Sidney Wilkerson-Hill
Keyword(s):  
Natural Product ◽  
Intramolecular Cyclization ◽  
Conjugate Addition ◽  
Secondary Amines ◽  
Addition Reactions ◽  
Cyclization Reactions ◽  
Carbon Nucleophiles ◽  
Multicomponent Coupling

Dihalomucononitriles were synthesized and their reactivity evaluated to assess their ability to function as linchpin reagents. Bis(2-chloroacrylonitrile) and bis(2-bromoacrylonitrile) were synthesized from 2,13-benzothiadiazole and shown to undergo conjugate addition reactions with both nitrogen (40–95% yield) and carbon nucleophiles (72–93% yield). Secondary amines were found to undergo monoadditions while carbon nucleophiles added twice. The sequence of addition of the nucleophiles could be controlled giving mixed addition products. The multicomponent coupling products could then be converted to natural product-like motifs using intramolecular cyclization reactions.

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