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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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A novel application of DDQ as electrophile in the Nenitzescu reaction

U Kucklaender1, R Bollig, W Frank

  • 1Institute of Pharmaceutical and Medicinal Chemistry, Heinrich-Heine-University Duesseldorf, Duesseldorf, Germany. kucklaen@uni-duesseldorf.de

Bioorganic & Medicinal Chemistry
|April 5, 2011
PubMed

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Diels–Alder Reaction: Characteristics of Dienophiles

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
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Diels–Alder Reaction: Characteristics of Dienes

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Characteristics of the diene
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Diazonium Group Substitution: –OH and –H

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