Orthoamide und Iminiumsalze, CII. Umsetzungen eines Orthoamids der Phenylpropiolsäure mit tertiären CH-aciden Verbindungen

N,N′,N′′-peralkylated guanidinium chlorides and N,N′,N′′-peralkylated guanidines were prepared from N,N′-peralkylated chloroformamidinium chlorides. The alkylation of the guanidines affords N,N′,N′′-persubstituted guanidinium chlorides bromides, iodides, alkylsulfates, and tetrafluoroborates. Guanidinium tricyanomethanides and tetracyanopropenides were prepared from the chlorides and iodides by anion metathesis. The reaction of guanidinium halogenides with borontrifluoride etherate, triethyloxonium tetrafluoroborate or sodiumtetrafluoroborate delivers guanidinium tetrafluoroborates. Guanidinium saccharinides, cyanates, thiocyanates, trifluoromethansulfonates, bis(trifluormethansulfonyl)imides, hexacyanoferrates(II/III), tetracyanonickolates and tetrathiocyanatocobaltates were prepared from the corresponding guanidinium chlorides and tetrafluoroborates by anion exchange.

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Orthoamide und Iminiumsalze, CIII. Synthese von N,N′,N′′-peralkylierten Guanidiniumsalz-basierten ionischen Flüssigkeiten durch Anionenmetathese

Kantlehner

Mezger

Tiritiris

et al. 2021

Zeitschrift Für Naturforschung B

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Orthoamide und Iminiumsalze, CV. Umsetzungen von Orthoamiden der Alkincarbonsäuren mit Carbonsäureamiden

Kantlehner

Lehmann

Edelmann

et al. 2022

Zeitschrift Für Naturforschung B

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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.

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Orthoamide und Iminiumsalze, CII. Umsetzungen eines Orthoamids der Phenylpropiolsäure mit tertiären CH-aciden Verbindungen

Cited by 2 publications

References 25 publications

Orthoamide und Iminiumsalze, CIII. Synthese von N,N′,N′′-peralkylierten Guanidiniumsalz-basierten ionischen Flüssigkeiten durch Anionenmetathese

Orthoamide und Iminiumsalze, CIII. Synthese von N,N′,N′′-peralkylierten Guanidiniumsalz-basierten ionischen Flüssigkeiten durch Anionenmetathese

Orthoamide und Iminiumsalze, CV. Umsetzungen von Orthoamiden der Alkincarbonsäuren mit Carbonsäureamiden

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