Diastereoselektive Ringschlußreaktion zum Pyrrolodiazepino-chinolin

✍ Scribed by Gündel, Wolf-H. ;Bohnert, Sabine

• Publisher: John Wiley and Sons
• Year: 1986
• Tongue: English
• Weight: 235 KB
• Volume: 1986
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.198619860618

✦ Synopsis

Quaternary salts of N-(3-quinolinylcarbonyl)-~-prolinamide 5 b, c cyclize under the influence of base to pyrrolodiazepino-quinolines 6 b, c with an additional dissymmetric carbon atom. The reaction yields the pure enantiomers 6b, c with high diastereoselectivity. The salt with a sarcosine moiety (Sa) forms the racemic diazepino-quinoline 6a under the same conditions. Das Pyrrolo[ 1,2-a][1,4]benzodiazepin-Geriist ist das gemeinsame Strukturelement der Antibiotika Anthramycin, Sibiromycin u. a. ',*I. Aus der Antitumorwirkung dieser Tricyclen resultierte das Interesse an derartigen Ringsystem 3-6). Bislang nicht bekannte Derivate, in C-CL H-X-C02C2H5 ~c -x -c 0 2 c 2 H 5 P NH, 2 ___o 1 3 ~~-" ' " " . __cz C,H5-CHiBr