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Direct preparation of pyrrolizidines using imines and isonitriles


Gademann, Karl; Kerschgens, Isabel (2015). Direct preparation of pyrrolizidines using imines and isonitriles. Synthesis, 47(20):3153-3160.

Abstract

An acid mediated annulation reaction for the formation of 7a-substituted unnatural pyrrolizidines is described. To reach this goal, the pyrroline 3-(3,4-dihydro-2H-pyrrol-5-yl)propan-1-ol is reacted with a large variety of isonitriles directly resulting in the target compounds. The reaction is operationally simple and tolerates air and water, and the resulting pyrrolizidines can be further transformed to the corresponding oxidized and reduced derivatives.

Abstract

An acid mediated annulation reaction for the formation of 7a-substituted unnatural pyrrolizidines is described. To reach this goal, the pyrroline 3-(3,4-dihydro-2H-pyrrol-5-yl)propan-1-ol is reacted with a large variety of isonitriles directly resulting in the target compounds. The reaction is operationally simple and tolerates air and water, and the resulting pyrrolizidines can be further transformed to the corresponding oxidized and reduced derivatives.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:pyrrolizidines - isonitriles - cyclizations - pyrrolines
Language:English
Date:9 July 2015
Deposited On:22 Aug 2017 16:04
Last Modified:02 Oct 2019 09:49
Publisher:Georg Thieme Verlag
ISSN:0039-7881
OA Status:Green
Publisher DOI:https://doi.org/10.1055/s-0034-1380433

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