Aza-Diels-Alder Reaction Between 1,2-Diaza-1,3-dienes and β-Aryl-α,β-unsaturated Carbonyl Compounds. Easy One-pot Entry to 2’-Oxo-imidazo[1’,5’- f]tetrahydropyridazine

Author(s): Orazio A. Attanasi , Luca Bianchi , Maurizio D’Auria , Gianfranco Favi , Fabio Mantellini , Rocco Racioppi .

Journal Name: Current Organic Synthesis

Volume 10 , Issue 6 , 2013

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Abstract:

1,2-Diaza-1,3-dienes bearing electron withdrawing groups react with α,β-unsaturated carbonyl compounds by means of an uncommon aza-Diels-Alder reaction furnishing functionalized tetrahydropyridazines. The regioselectivity of the process is governed by the nature of the β substituent of the α,β-unsaturated carbonyl compounds. In the case of β aryl-α,β-unsaturated carbonyl compounds the formed tetrahydropyridazines present the carbonyl group in a suitable position to undergo a further cyclization process that furnish new 2’-oxo-imidazo[1’,5’-f]tetrahydropyridazine derivatives.

Keywords: 1, 2-Diaza-1, 3-dienes, α, β-unsaturated carbonyl compounds, fused heterocycles, tetrahydropyridazines, imidazoles, DFT calculations.

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Article Details

VOLUME: 10
ISSUE: 6
Year: 2013
Page: [951 - 960]
Pages: 10
DOI: 10.2174/157017941006140206104854
Price: $58

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