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Nitroso Diels-Alder Cycloadducts Derived From N-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity

Andrea Menichetti1, Francesco Berti1, Mauro Pineschi1

  • 1Department of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, Italy.

Molecules (Basel, Switzerland)
|February 5, 2020
PubMed

Keywords:
diversity oriented synthesisfunctionalized piperidinesfunctionalized pyrrolesheterobicyclic compoundsnitroso Diels-Alder

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
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Conformation
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In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction. 
Characteristics of Dienophiles
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