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

• Published in: Journal of organic chemistry Vol. 75; no. 24; pp. 8533 - 8541
• Main Authors: Bhadra, Sukalyan, Adak, Laksmikanta, Samanta, Subhas, Maidul Islam, A. K. M, Mukherjee, Manabendra, Ranu, Brindaban C
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 17.12.2010; Amer Chemical Soc
• Subjects: Aluminum Oxide - chemistry; Aziridines - chemistry; Benzoxazines - chemistry; Catalysis; Catalysts: preparations and properties; Chemistry; Chemistry, Organic; Copper - chemistry; Cyclization; Epoxy Compounds - chemistry; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Kinetics and mechanisms; Molecular Structure; Organic chemistry; Physical Sciences; Preparations and properties; Reactivity and mechanisms; Science & Technology; Stereoisomerism; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; SUBSTITUTION; POTENT; DESIGN; HETEROCYCLES; COMPLEXES; ANTAGONISTS; DERIVATIVES; EFFICIENT; 3,4-DIHYDRO-2H-1,4-BENZOXAZINES; DOMINO; Copper II; One pot reaction; Catalytic reaction; Regioselectivity; Nitrogen heterocycle; Ligand; Aziridine derivatives; Air; Oxygen heterocycle; Ring cleavage; Cyclization; Functionalization; Epoxide; Reaction mechanism; Green chemistry; Recycling; Alumina; Catalyst; Catalyst support
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo101916e

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.