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2-aminothiophenes from triacetonamine: A convenient way to novel sterically hindered piperidine derivatives

✍ Scribed by Ulrich Sensfuss; Wolf D. Habicher

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
196 KB
Volume
9
Category
Article
ISSN
1042-7163

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✦ Synopsis

Bicyclic 2-aminothiophenes 2, which are available by the Gewald reaction of 2,2,6,6-tetramethyl-4-piperidone (triacetonamine, 1), were employed in cyclizations to give new tricyclic thienopyridine and thienopyrimidine derivatives, without protection of the piperidine nitrogen, whereas methylation of 2 occurred exclusively at the piperidine nitrogen. Acylation of 2 in the presence of a tertiary amine yielded N-thienyl imides, due to the high NH acidity of the intermediate N-thienyl amides. Similarly, benzylation of an N-thienyl amide proceeded readily in sodium ethoxide solution. α­§ 1998

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