Imidoylketenes 11 and oxoketenimines 12 are generated by flash vacuum thermolysis of Meldrum's acid derivatives 9, pyrrolediones 17 and 18, and triazole 19 and are observed by IR spectroscopy. Ketenimine-3-carboxylic acid esters 12a are isolable at room temperature. Ketenes 11 and ketenimines 12 undergo rapid interconversion in the gas phase, and the ketenes cyclize to 4-quinolones 13. When using an amine leaving group in Meldrum's acid derivatives 9c, the major reaction products are aryliminopropadienones, ArN=C=C=C=O (15). The latter react with 1 equiv of nucleophile to produce ketenimines 12 and with 2 equiv to afford maIonic acid imide derivatives 16. N-Arylketenimine-C-carboxamides 12c cyclize to quinolones 13c via the transient amidinoketenes 11c at temperatures of 25-40 degrees C. This implies rapid interconversion of ketenes and ketenimines by a 1,3-shift of the dimethylamino group, even at room temperature. This interconversion explains previously poorly understood outcomes of the ynamine-isocyanate reaction. The solvent dependence of the tautomerism of 4-quinolones/4-quinolinols is discussed. Rotational barriers of NMe2 groups in amidoketenimines 12c and malonioc amides and amidines 16 (24) are reported.

Aryliminopropadienone−C-Amidoketenimine− Amidinoketene−2-Aminoquinolone Cascades and the Ynamine−Isocyanate Reaction

Tautomerism and acidity in 4-quinolone-3-carboxylic acid derivatives

Polyine, 9. Umsetzungen von Butadiindiaminen und eines Butadiinamins mit Arylisocyanaten

Ynediamine 1 is a versatile synthon in heterocyclic chemistry. It reacts with arylisocyanates to furnish new diaminoquinolones 4 and 5 by rearrangement as confirmed by X-Ray measurements. They react with phosgene by loss of methyl chloride whereby an oxazolone ring is formed.

New Aminoquinolones From Arylisocyanates and Ynediamine

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New Aminoquinolones From Arylisocyanates and Ynediamine