ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
A New Synthesis of N-Alkylated 3,3-DialkylpiperidinesIn 1- and 4-position suitably substituted 2-aza-1,3-butadienes (e.g. 5) do not react with acrylonitrile according to a Diels-Alder reaction but in a Michael addition to give 5-(1-alkenylimino)-4,4-dialkylpentanenitriles (e.g. 8), which can be transformed into 1,3,3-trialkylpiperidines (9) by hydrogenating cyclization. The same piperidines are also obtained by cyclization of the azomethines 4 of 4,4-dialkyl-4-formylbutanenitriles.
Notes:
In 1- und 4-Stellung geeignet substituierte 2-Aza-1,3-butadiene (z.B. 5) reagieren mit Acrylnitril nicht nach Diels-Alder, sondern führen in einer Michael-Addition zu 5-(1-Alkenylimino)-4,4-dialkylpentannitrilen (z. B. 8), die sich durch hydrierende Cyclisierung in 1,3,3-Trialkylpiperidine (9) umwandeln lassen. Die gleichen Piperidine sind auch durch Cyclisierung der Azomethine 4 von 4,4-Dialkyl-4-formylbutannitrilen zugänglich.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19781110508
Permalink