Synthesis of Tetrahydropyridazine Amino Acid Derivatives by a Formal [4+2] Cycloaddition Reaction of 1,2-Diaza-1,3-dienes with Dehydroalanine Esters.

Title:Synthesis of Tetrahydropyridazine Amino Acid Derivatives by a Formal [4+2] Cycloaddition Reaction of 1,2-Diaza-1,3-dienes with Dehydroalanine Esters.

Volume: 10 Issue: 5

Author(s): Orazio A. Attanasi, Gianfranco Favi, Gianluca Giorgi, Fabio Mantellini, Giada Moscatelli and Giovanni Piersanti

Affiliation:

Keywords: Cycloaddition reaction, dehydroalanine esters, 1, 2-Diaza-1, 3-dienes, N, N-disubstituted quaternary center, nitrogen heterocycles, tetrahydropyridazine amino acids.

Abstract: A highly efficient formal inverse electron demand aza Diels–Alder reaction of 1,2-diaza-1,3-dienes (DDs) is accomplished using dehydroalanine esters (DhAs) as electron-rich dienophiles. Both diastereoisomers of unprecedented ,-disubstituted cyclic tetrahydropyridazine amino acids were obtained in excellent yields, in refluxing acetonitrile without activation.

Cite this article as:

Attanasi A. Orazio, Favi Gianfranco, Giorgi Gianluca, Mantellini Fabio, Moscatelli Giada and Piersanti Giovanni, Synthesis of Tetrahydropyridazine Amino Acid Derivatives by a Formal [4+2] Cycloaddition Reaction of 1,2-Diaza-1,3-dienes with Dehydroalanine Esters., Current Organic Synthesis 2013; 10 (5) . https://dx.doi.org/10.2174/1570179411310050011