Copper(II)/copper(I)-catalyzed aza-Michael addition/click reaction of in situ generated alpha-azidohydrazones: synthesis of novel pyrazolone-triazole framework.
A one-pot Cu(II)-catalyzed aza-Michael addition of trimethylsilyl azide to 1,2-diaza-1,3-dienes and Cu(I)-catalyzed 1,3-dipolar cycloaddition of in situ generated alpha-azidohydrazones with alkynes is reported. This process combining two consecutive steps with recycling of the catalyst (Cu(OAc)(2).H(2)O) represents a useful protocol for the smooth synthesis of novel pyrazolone-triazole derivatives.
Attanasi
Orazio A
OA
Istituto di Chimica Organica, Università degli Studi di Urbino Carlo Bo, Via I Maggetti 24, 61029 Urbino (PU), Italy.
Favi
Gianfranco
G
Filippone
Paolino
P
Mantellini
Fabio
F
Moscatelli
Giada
G
Perrulli
Francesca R
FR
D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D006835:Hydrazones / Q000737:chemistry; D015394:Molecular Structure; D047069:Pyrazolones / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D001386:Azides; D006835:Hydrazones; D047069:Pyrazolones; D014230:Triazoles; C038362:pyrazolone; D003300:Copper