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Synfacts 2011(6): 0605-0605  
DOI: 10.1055/s-0030-1260457
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Zinc(II)-Catalyzed Synthesis of Poly-functionalized Pyrroles

Contributor(s): Victor Snieckus, Toni Rantanen
O. A. Attanasi, S. Berretta, L. De Crescentini, G. Favi, G. Giorgi, F. Mantellini*, S. Nicolini
Universitá degli Studi di Urbino ‘Carlo Bo’ and Universitá degli Studi di Siena, Italy
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Publication History

Publication Date:
19 May 2011 (online)

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Significance

Reported are full details of the ­preliminary communication (O. A. Attanasi et al. Adv. Synth. Catal. 2009, 351, 715) concerning the reaction of 1,2-diaza-1,3-dienes A with amines B and dialkyl acetylene dicarboxylates C catalyzed by zinc triflate to afford tetrasubstituted pyrroles F. Additionally, details are disclosed on the two-step, one-pot synthesis of 3-hydroxypyrroles H, not requiring any catalyst. The overall yields are modest, but as the starting materials are inexpensive and/or easily prepared, this offsets the deficit. Substrate scope was well studied and interesting linked bis-pyrroles were also prepared [R³NH2 = H2N(CH2)xNH2].