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

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

Journal Name: Current Organic Synthesis

Volume 10 , Issue 5 , 2013

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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.

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Article Details

VOLUME: 10
ISSUE: 5
Year: 2013
Page: [803 - 811]
Pages: 9
DOI: 10.2174/1570179411310050011
Price: $58

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