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Reactivity of Dipyrromethanes towards Azoalkenes: Synthesis of Functionalized Dipyrromethanes, Calix[4]pyrroles, and Bilanes
Author(s) -
Lopes Susana M. M.,
Lemos Américo,
Pinho e Melo Teresa M. V. D.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402944
Subject(s) - chemistry , hydrazone , reactivity (psychology) , organic chemistry , combinatorial chemistry , medicine , alternative medicine , pathology
The introduction of side chains at the 1‐ and 9‐positions of dipyrromethanes was explored by using the hetero‐Diels–Alder reaction of azoalkenes. New 5,5′‐diethyldipyrromethanes and 5‐phenyldipyrromethanes that were functionalized with open‐chain hydrazone moieties, including derivatives with tetrazolyl groups, were prepared. Furthermore, the synthesis of new calix[4]pyrroles and bilanes was achieved by employing the bis(hetero‐Diels–Alder) reaction of azoalkenes with 5,5′‐diethyldipyrromethane.