Premium
Diversity‐Oriented Synthesis of Complex Pyrrole‐Based Architectures from Very Simple Starting Materials
Author(s) -
Leonardi Marco,
Estévez Verónica,
Villacampa Mercedes,
Menéndez J. Carlos
Publication year - 2019
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.201900044
Subject(s) - pyrrole , chemistry , domino , intramolecular force , furan , combinatorial chemistry , ring closing metathesis , metathesis , ring (chemistry) , organic chemistry , catalysis , polymerization , polymer
The build/couple/pair strategy was applied to the generation of 18 structurally diverse scaffolds built around pyrrole cores. The couple phase, involving the first application of a mechanochemical multicomponent reaction for this purpose, afforded pyrrole derivatives that were transformed into some unusual fused heterocyclic systems using a domino process initiated by a Cu‐catalyzed cross coupling or intramolecular furan Diels‐Alder reactions. Because of the high current importance of macrocycles in drug discovery, the synthesis of macrocyclic libraries was also investigated using a pseudo five‐component double Hantzsch pyrrole synthesis followed by ring‐closing metathesis or the one‐pot generation of two pyrrole rings.