Orthoamide und Iminiumsalze, CIX. Umsetzungen von Orthoamiden der Alkincarbonsäuren mit Diolen, Ethandithiol und CH-aciden Nitroverbindungen
Author:
Kantlehner Willi12, Edelmann Kai2, Vettel Markus2, Lehmann Hansjörg2, Mezger Jochen2, Wolfgang Frey 2
Affiliation:
1. Abteilung Technische Organische Synthesechemie und Katalyseforschung , Institut für Angewandte Forschung, Hochschule Aalen , Beethovenstraße 1, 73430 Aalen , Germany 2. Institut für Organische Chemie, Universität Stuttgart , Pfaffenwaldring 55, 70569 Stuttgart , Germany
Abstract
AbstractOrthoamides of alkyne carboxylic acids17react with 1,2- and 1,3-dioles to give vinylogous cyclic urea acetals. Analogous reactions with ethandithiol deliver vinylogous thioureas. The condensation of orthoamides17with 3,5-dimethyl-4-nitroisoxazol affords 1,1-diamino-butadiene derivatives. From nitro acetaldehyde diethylacetal and orthoamides17can be prepared reactive vinylogous urea acetals, which condense with cyano-acetic acid ester under formation of 7,7-diamino-2,4,6-hexatrienecarboxylic acid esters. 5,5-Bis(dimethylamino)-2-nitro-2,4-butadienecarboxylic acid esters, which are accessible from the orthoamides17and nitro acetic ester, cyclize to give 5-dimethylamino-pyrrole-2-carboxylic acid esters on treatment with zinc/acetic acid.
Publisher
Walter de Gruyter GmbH
Subject
General Chemistry
Reference25 articles.
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