Orthoamide und Iminiumsalze, CV. Umsetzungen von Orthoamiden der Alkincarbonsäuren mit Carbonsäureamiden
Author:
Kantlehner Willi12, Lehmann Hansjörg2, Edelmann Kai2, Mezger Jochen2, Frey Wolfgang2
Affiliation:
1. Institut für Angewandte Forschung, Abteilung Technische Organische Synthesechemie und Katalyseforschung, Hochschule Aalen , Beethovenstr. 1 , D-73430 Aalen , Germany 2. Institut für Organische Chemie, Universität Stuttgart , Pfaffenwaldring 55 , 70569 Stuttgart , Germany
Abstract
Abstract
The reaction of an orthoamide derivative of phenylpropiolic acid (22a) with primary and secondary amides gives rise to the formation of a wide spectrum of reaction products. The reaction of 22a with formamide delivers a N-carbamoyl-cinnamic acid amidine, wheras the analogous reaction with methylene-diformamide leads to a ketenaminal, which is substituted in β-position by a N-formylimino group. From the orthoamide 22a and phthalimide a phthalic acid amide amidine is obtained. In contrast the reaction of diformamide with 22a affords a β-imino enamine. 2,6-Diaminopyridines can be obtained from 22a with acetamide, propionamide and butyramide in low yields. The pyridines are characterized as perchlorates. From 22a and benzamide a 4-amino-2,6-diphenylpyrimidine is obtained in low yield. In the reaction of the closely related orthoamide derivative of 4-Cl-phenylpropiolic acid 22b with benzamide are isolated as a further products two pyrimidine derivatives. A pyrimidinone and a vinylogous thiourea can be obtained from 22a and urea and thiourea, respectively.
Publisher
Walter de Gruyter GmbH
Subject
General Chemistry
Reference58 articles.
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