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Iron(III) Salt‐Catalyzed Nazarov Cyclization/Michael Addition of Pyrrole Derivatives
Author(s) -
Fujiwara Masamune,
Kawatsura Motoi,
Hayase Shuichi,
Nanjo Masato,
Itoh Toshiyuki
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800702
Subject(s) - chemistry , pyrrole , catalysis , salt (chemistry) , yield (engineering) , ketone , methyl vinyl ketone , derivative (finance) , michael reaction , perchlorate , medicinal chemistry , selectivity , organic chemistry , combinatorial chemistry , ion , materials science , economics , financial economics , metallurgy
The Nazarov cyclization of two types of pyrrole derivatives was effectively catalyzed by 5 mol% alumina‐supported iron(III) perchlorate [Fe(ClO 4 ) 3 ⋅Al 2 O 3 ] 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.