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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

[ Vol. 10 , Issue. 6 ]

Author(s):

Orazio A. Attanasi, Luca Bianchi, Maurizio D’Auria, Gianfranco Favi, Fabio Mantellini and Rocco Racioppi   Pages 951 - 960 ( 10 )

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.

Affiliation:

Sezione di Chimica Organica e Sostanze Organiche Naturali, Dipartimento STeVA, Universita degli Studi di Urbino “Carlo Bo”, Via I Maggetti 24, 61029 Urbino (PU), Italy.



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