Anwendung der «Zip»-Reaktion zur Synthese eines 53gliedrigen Polyaminolactams. 8. Mitteilung über Umamidirungsreaktionen

✍ Scribed by Urs Kramer; Armin Guggisberg; Manfred Hesse

• Publisher: John Wiley and Sons
• Year: 1979
• Tongue: German
• Weight: 529 KB
• Volume: 62
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19790620727

✦ Synopsis

Use of the ‘Zip’ reaction for the synthesis of a 53‐membered polyminolactam

The synthesis of N‐(39‐amino‐4, 8, 12, 16, 20, 24, 28, 32, 36‐nonaaza‐nonatriacontyl)‐12‐dodecanlactam (1)In ‘5’ wurden die Verbindungen 1 als 1‐(39‐Amino‐4,8,12,16,20,24,28,32,36‐nonaazanonatriacontyl)‐1‐azacyclotridecan‐2‐on, 4 als 7‐Chlor‐1‐phthalimido‐4‐tosyl‐4‐azaheptan, 5 als 7‐Jod‐1‐phthalimido‐4‐tosyl‐4‐azaheptan und 20 als 1,5,9,13,17,21,25,29,33,37,41‐Undecaazatripentacontan‐42‐on bezeichnet.

has been described. The formation of synthon
2
, used for the chain extension of the known
12
[6] shown in
Scheme 2
, is demonstrated in
Scheme 1
. In presence of base (KAPA‐reagent),
1
undergoes the so called ‘Zip’‐reaction resulting in a ring‐expansion by 40 members which leads to
20
.