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Preparation of Substituted Alkylpyrroles via Samarium-Catalyzed Three-Component Coupling Reaction of Aldehydes, Amines, and Nitroalkanes

1998; American Chemical Society; Volume: 63; Issue: 18 Linguagem: Inglês

10.1021/jo980435t

1520-6904

Hiroyuki Shiraïshi, Takayuki Nishitani, Satoshi Sakaguchi, Yasutaka Ishii,

Chemical Synthesis and Reactions

Pyrroles were synthesized by three-component coupling reaction of aldehydes, amines, and nitroalkanes in the presence of a catalytic amount of a samarium species under mild conditions. The reaction is considered to involve the coupling of α,β-unsaturated imines, which are provided by the samarium-catalyzed aldol-type condensation of imines generated from amines and aldehydes, with nitroalkanes. In the case of the three-component coupling of α,β-unsaturated aldehydes (or ketones) with amines and nitroalkanes, alkylpyrroles were obtained by only heating in the absence of any catalyst. For instance, a mixture of butylamine, 2-butylidenecyclohexanone, and nitroethane, allowed to react at 60 °C for 15 h, produced isoindole, 4r, which is difficult to prepare by conventional methods, in 39% yield.