Antiaromatische Verbindungen; 28.1Eine Synthese von Pyrrol-Derivaten aus Tri-tert-butylazet und Isonitrilen oder Kohlenmonoxid
- 1 January 1990
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1990 (09) , 834-840
- https://doi.org/10.1055/s-1990-27029
Abstract
Antiaromatic Compounds; 28.1. A Synthesis of Pyrrole Derivatives from Tri-tert-butylazete and Isonitriles or Carbon Monoxide The kinetically stabilized azete 4 reacts with isonitriles 5 in a sequence of [4 + 1] cycloaddition and ring-opening steps to yield 2- and 3-imino substituted 2H- and 3H-pyrrole derivatives 8,9. The α-methylene isonitriles 10 react analogously, but the formation of 2- and 3-iminopyrroles is still followed by an [1,5]-shift which leads to 2- and 3-aminopyrroles 13,14. With carbon monoxide the azete 4 is transformed into the 2H-pyrrole-2-one and 3H-pyrrole-3-one 18 and 19.Keywords
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