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Die «Zip»‐Reaktion: Eine neue Ringerweiterungsreaktion. Synthese von 17‐, 21‐ und 25‐gliedrigen Polyaminolactamen . 4. Mitteilung über Umamidierungsreaktionen
Author(s) -
Kramer† Urs,
Guggisberg Armin,
Hesse Manfred,
Schmid† Hans
Publication year - 1978
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19780610417
Subject(s) - chemistry , acrylonitrile , ring (chemistry) , yield (engineering) , stereochemistry , organic chemistry , materials science , copolymer , metallurgy , polymer
The Zip‐reaction: A New Method for the Synthesis of Macrocyclic Polyaminolactams The 21‐ and 25‐membered aminolactams 11 and 25 were synthesized from the 13‐membered lactam 4 . To introduce the ring enlargement unit (a propylamino group) 4 was N ‐alkylated using acrylonitrile and the resulting product hydrogenated. Repetition of this reaction sequence gave 3 , which was converted in the presence of base in 90% yield to the ring‐enlarged macrocyclic base 11 ( Scheme 2 ). In a similar but stepwise synthesis consisting of two separate ring‐enlargement reactions 4 was transformed to 11 via 13 ( Scheme 4 ). Introducing three ringenlargement units into 4 the 25‐membered aminolactam 25 was synthesized in 84% yield ( Scheme 5 ). The mechanism of the ring‐enlargement reaction is given in Scheme 3 . In comparison to a zip‐fastener or zipper this reaction is called “zipreaction”.