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Amidinoethylation-a new reaction-IV. The amidinoethylation of alcohols: a facile synthesis of 3-alkoxy-N,N'-substituted-propanamidines1 1 Acrylamidines and polyacrylamidines VII, for part VI see R. Fuks and M. Van Den Bril, Tetrahedron 37, 2895 (1981).

par Van Den Bril, Marc ;Fuks, Robert
Référence Tetrahedron, 37, 16, page (2905-2908)
Publication Publié, 1981

Article révisé par les pairs

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Résumé :

The amidinoethylation of alcohols takes place by the addition of sodium alkoxides 2 (R1 = Me, Et) to the CC double bond of a variety of N,N'-substituted-propenamidines 1 (Method A). This illustrates the activation of the CC double bond by the conjugated amidine function and provides a new class of Michael acceptors for alcohols. However, this activation is poorer than with other nucleophiles or Michael acceptors. The amidinoethylation makes available 3-alkoxy-N,N'-substituted-amidines not easily accessible by other classical methods. However, it is demonstrated that the general N,N'-substituted-amidine synthesis via the nitrilium salts can also apply to nitrile compounds having an alkoxygroup present on the molecule (method B). Since the cyanoethylation of alcohols (4) is a very fast and facile reaction the method B is the preferred strategy for the synthesis of 3-alkoxy-N,N'-substituted-propanamidines 3. © 1981.