Alumina-supported Cu(II), a versatile and recyclable catalyst for regioselective ring opening of aziridines and epoxides and subsequent cyclization to functionalized 1,4-benzoxazines and 1,4-benzodioxanes.
An easily accessible catalyst, alumina-supported copper(II), efficiently catalyzes the ring opening of aziridines and epoxides followed by cyclization of the corresponding intermediate to produce a variety of functionalized 1,4-benzoxazines and 1,4-benzodioxanes, respectively, in one pot without any ligand in high yields. The ring cleavages of aziridines and epoxides are highly regioselective. The catalyst is inexpensive, non-air-sensitive, environmentally friendly, and recyclable. The function of the catalyst and the reaction pathway are postulated. This protocol is successfully utilized for the formation of three carbon-heteroatom bonds, namely, C-O, C-N, and C-S, in one pot.
Department of Organic Chemistry, Indian Association for theCultivation of science, Jadavpur, Kolkata-700031, India.
Sukalyan
S
Bhadra
Laksmikanta
L
Adak
Subhas
S
Samanta
A K M
AK
Maidul Islam
Manabendra
M
Mukherjee
Brindaban C
BC
Ranu
D000537:Aluminum Oxide / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D048588:Benzoxazines / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D001388:Aziridines; D048588:Benzoxazines; D004852:Epoxy Compounds; D003300:Copper; D000537:Aluminum Oxide