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

Title: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

Volume: 10 Issue: 6

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

Affiliation:

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

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.

Cite this article as:

Attanasi A. Orazio, Bianchi Luca, D’Auria Maurizio, Favi Gianfranco, Mantellini Fabio and Racioppi Rocco, 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, Current Organic Synthesis 2013; 10 (6) . https://dx.doi.org/10.2174/157017941006140206104854