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Synthesis of Radialene‐Shaped Pyrroles by Multiple‐Anion‐Capture Reactions of 1,3‐Dianions
Author(s) -
Langer Peter,
Döring Manfred,
Schreiner Peter R.,
Görls Helmar
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20010618)7:12<2617::aid-chem26170>3.0.co;2-f
Subject(s) - chemistry , oxalic acid , regioselectivity , ion , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis
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.