Zur Aminolyse von Bis-Imidoylchloriden der Oxals�ure II. Umsetzung mit Diaminen und Aminoalkoholen
In: Journal f�r Praktische Chemie/Chemiker-Zeitung, Jg. 337 (1995), S. 508-515
Online
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Zugriff:
On the Aminolysis of Bis-Imidoylchlorides of Oxalic Acid. II. Reaction with Aliphatic Diamines and Aminoalcohols The aminolysis of bis-imidoylchloride 1 derived from oxalic acid with several diamines and aminoalcohols was investigated. At room temperature diamines 2 as well as aminoalcohols 7 give mainly the cyclic amidines 3 and mixed amidine-imidates 8 in moderately up to good yields. While cis-1,2-diaminocyclohexane yields at room temperature the bicyclic amidine 3a, the trans isomer reacts to 3b only when heated for several hours. Depending on the conditions, the racemic 1,2-diaminopropane 2h gives derivatives of pyrazine 3h or the open-chain amidine 5 resulting from an oxidative aromatization and subsequent hydrolysis. Histamine 2i and 1,8-diamino-3,6-dioxaoctane 2p react selectively with 1 to seven- respectively twelve-membered heterocycles 3i and 3p. The mixed aliphatic and aromatic diamines 2n, o show an anomalous behaviour leading to 2,2′-bis-chinazolines 3n, o. In comparison with acyclic oxalic amidines the new cyclic derivatives show less molecular dynamic in their nmr spectra. In some cases, a s-trans-arrangement of the amidine substructure was observed.
Titel: |
Zur Aminolyse von Bis-Imidoylchloriden der Oxals�ure II. Umsetzung mit Diaminen und Aminoalkoholen
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Autor/in / Beteiligte Person: | Lindauer, Dirt ; Billert, Thomas ; Görls, Helmar ; Beckert, Rainer ; Döring, Manfred |
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Zeitschrift: | Journal f�r Praktische Chemie/Chemiker-Zeitung, Jg. 337 (1995), S. 508-515 |
Veröffentlichung: | Wiley, 1995 |
Medientyp: | unknown |
ISSN: | 1521-3897 (print) ; 0941-1216 (print) |
DOI: | 10.1002/prac.199533701107 |
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