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Reaction of the 5-Azoniafulvene Ion with Enamines: A New Approach to Pyrrolizines (1991)

Schärer, Daniel ; Jindra, Vladimir ; Bringhen, Alain O. ; [et al.]

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 74 (1991), S. 1817-1822

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The synthesis of N,N-dimethyl-N-[(pyrro-1-yl)methyl]anilinium chloride (14) and of the corresponding p-toluidinium salt 15 is described. These salts, when dissolved in polar solvents, are shown to be in equilibrium with 1-(chloromethyl)pyrrole (17) and thereby potentially with the 5-azoniafulvene ion (2). Consequently, they react under very mild conditions (MeCN, 60°) with enamines to give pyrrolizine derivatives in acceptable yield (40-50°). The process is rationalized in terms of an initial Mannich-type reaction which is immediately followed by acyclization.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19910740824

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