Synthesis of Radialene-Shaped Pyrroles by Multiple-Anion-Capture Reactions of 1,3-Dianions

✍ Scribed by Peter Langer; Manfred Döring; Peter R. Schreiner; Helmar Görls

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 256 KB
• Volume: 7
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/1521-3765(20010618)7:12<2617::aid-chem26170>3.0.co;2-f

✦ Synopsis

A new multicomponent reaction (multiple-anion-capture reaction) of 1,3dianions 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.