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Iron(III) Salt-Catalyzed Nazarov Cyclization/Michael Addition of Pyrrole Derivatives

Authors

  • Masamune Fujiwara,

    1. Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan, Fax: (+81)-857-31-5259; phone: (+81)-857-31-5259
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  • Motoi Kawatsura,

    1. Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan, Fax: (+81)-857-31-5259; phone: (+81)-857-31-5259
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  • Shuichi Hayase,

    1. Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan, Fax: (+81)-857-31-5259; phone: (+81)-857-31-5259
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  • Masato Nanjo,

    1. Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan, Fax: (+81)-857-31-5259; phone: (+81)-857-31-5259
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  • Toshiyuki Itoh

    1. Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan, Fax: (+81)-857-31-5259; phone: (+81)-857-31-5259
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Abstract

The Nazarov cyclization of two types of pyrrole derivatives was effectively catalyzed by 5 mol% alumina-supported iron(III) perchlorate [Fe(ClO4)3⋅Al2O3 ] which provided the desired cyclization with high trans selectivity in good to excellent yield. The cyclized product was next reacted with a vinyl ketone in the presence of the same iron salt to afford the corresponding Michael product. A sequential type Nazarov/Michael reaction of pyrrole derivatives has also been accomplished; the synthetic route to 4,5-dihydrocyclopenta[b]pyrrol-6(1 H)-one derivative 5 or 5,6-dihydrocyclopenta[b]pyrrol-4(1 H)-one derivative 6 has thus been established using a very economical iron catalyst.

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