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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