Premium
Metal‐Free Cyclotrimerization for the De Novo Synthesis of Pyridines
Author(s) -
Kral Karolin,
Hapke Marko
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201007647
Subject(s) - cycloaddition , chemistry , metal , functional group , group (periodic table) , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , polymer
Two routes, one destination : The metal‐free, uncatalyzed [2+2+2] cycloaddition of cyanodiynes can proceed through two different reaction cascades, both yielding pyridines as products (see scheme). The unactivated cyano group can act either as an enophile in Alder–ene or as a dienophile in hetero‐Diels–Alder reactions—both of which are rather uncommon for this well‐known functional group.