TY - JOUR

T1 - A new approach to the synthesis of 4-(N-aryl)carbamoylmethyl-4,5- dihydropyridazin-3(2H)-ones

AU - Stepakov, Alexander V.

AU - Kinzhalov, Michail A.

AU - Boitsov, Vitaly M.

AU - Stepakova, Liubov V.

AU - Starova, Galina L.

AU - Vyazmin, Sergey Yu

AU - Grinenko, Elena V.

PY - 2011/6/15

Y1 - 2011/6/15

N2 - Reaction of N-aryl substituted maleimides with aliphatic ketazines leads to the formation of 4,5-dihydropyridazin-3(2H)-ones in moderate yields. The reaction proceeds through 1,4-addition of an azine to the maleimide double bond, as confirmed by separation of the corresponding adducts in some cases, which are then converted into 4,5-dihydropyridazin-3(2H)-ones. In addition, the solid-state synthesis of 4,5-dihydropyridazin-3(2H)-ones is demonstrated for the first time.

AB - Reaction of N-aryl substituted maleimides with aliphatic ketazines leads to the formation of 4,5-dihydropyridazin-3(2H)-ones in moderate yields. The reaction proceeds through 1,4-addition of an azine to the maleimide double bond, as confirmed by separation of the corresponding adducts in some cases, which are then converted into 4,5-dihydropyridazin-3(2H)-ones. In addition, the solid-state synthesis of 4,5-dihydropyridazin-3(2H)-ones is demonstrated for the first time.

KW - 4,5-Dihydropyridazin-3(2H)-ones

KW - Aliphatic ketazines

KW - Michael addition product

KW - Microwave irradiation

KW - N-Arylmaleimides

KW - Solvent-free conditions

UR - http://www.scopus.com/inward/record.url?scp=79956055814&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2011.04.038

DO - 10.1016/j.tetlet.2011.04.038

M3 - Article

VL - 52

SP - 3146

EP - 3149

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 24

ER -