Synthesis of radialene-shaped pyrroles by multiple-anion-capture reactions of 1,3-dianions.
A new multicomponent reaction (multiple-anion-capture reaction) of 1,3-dianions with nitriles and oxalic acid-bis(imidoyl)chlorides is reported. This process allows for an efficient and regioselective synthesis of a variety of radialene-shaped pyrroles which constitute structurally new and interesting heterocyclic systems. The cyclization products can be considered as aza-analogues of the pharmacologically relevant substance class of 3-acetyltetramic acids. A rationalization of the experimental results is given based on quantum chemical computations.
Langer
P
P
Institut für Organische Chemie der Georg-August-Universität Göttingen, Germany. planger@gwdg.de
Döring
M
M
Schreiner
P R
PR
Görls
H
H
D000838:Anions; D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D009570:Nitriles; D010070:Oxalates; D011758:Pyrroles / Q000138:chemical synthesis*
D000838:Anions; D009570:Nitriles; D010070:Oxalates; D011758:Pyrroles