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Current Organic Synthesis

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

DOI: 10.2174/1570179411310050011

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

Page: [803 - 811] Pages: 9

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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.

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