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Propyne Iminium Salts and Isoquinoline – 1 : 1 and 2 : 1 Adducts
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Philipp Kratzer
Published/Copyright:
June 2, 2014
The reaction of equimolar amounts of propyne iminium trifluoromethanesulfonates 1a, b and isoquinoline yielded, after hydrolytic work-up, the N-(3-oxoprop-1-en-1-yl)isoquinolinium salts 4a, b in modest yields. Monitoring of the reaction by 1H NMR spectroscopy indicated the formation of salts 4, 3-isoquinolinio-substituted propene iminium salts 3, and N,N,N',N'-tetramethylvinamidinium salts 5 as the major components. The expected aminoallenes (2-(3-(dimethylamino)allen-1- yl)isoquinolinium triflates) 2 could not be detected in the reaction solutions. It is possible, however, to trap the aminoallene intermediates in a polar [4+2] cycloaddition reaction, as shown by the isolation of 2 : 1 adducts 7c, d in good yield from cyclopropyl-substituted propyne iminium triflates 1c, d and isoquinoline. Hydride abstraction from 7c, d yielded the 2,4-dicyclopropyl-1,3- bis((dimethyliminio)(aryl)methyl)pyrido[2,1-a]isoquinolinium tris(triflates) 8c, d.
Graphical Abstract
Propyne Iminium Salts and Isoquinoline – 1 : 1 and 2 : 1 Adducts
Keywords: Propyne Iminium Salts; Isoquinoline; Conjugate Addition; Aminoallene; Pseudo Three-Component Reaction
Received: 2014-2-17
Published Online: 2014-6-2
Published in Print: 2014-5-1
© 1946 – 2014: Verlag der Zeitschrift für Naturforschung
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Keywords for this article
Propyne Iminium Salts;
Isoquinoline;
Conjugate Addition;
Aminoallene;
Pseudo Three-Component Reaction
Articles in the same Issue
- Chemistry of Iminium Salts, Imines, and Related Compounds
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- Synthesis of Methyl 3-Azidothieno[2,3-b]pyridine-2-carboxylates and Application of the Huisgen Reaction
- Orthoamide und Iminiumsalze, LXXXVII [1]. Eine neue, einfache Synthese für 1,3-Dimethylthymin / Orthoamides and Iminium Salts LXXXVII [1]. A New and Facile Synthesis of 1,3-Dimethylthymine
- Orthoamide und Iminiumsalze, LXXXIV [1]. Die Synthese von starken Formylierungsmitteln im präparativen Großmaßstab: Tris(dichlormethyl)amin / Orthoamides and Iminiumsalts LXXXIV [1]. The Synthesis of Strong Formylating Reagents on a Large Preparative Scale: Tris(chloromethyl)amine
- Orthoamide und Iminiumsalze, LXXXV [1]. Die Synthese von starken Formylierungsmitteln im präparativen Großmaßstab: N,N,N',N'- Tetraformylhydrazin und Formyl-aalen [Tris(diformylamino)methan] / Orthoamides and Iminium Salts LXXXV [1]. The Synthesis of Strong Formylating Reagents on a Large Preparative Scale: N;N;N';N'-Tetraformylhydrazine and Formyl-aalen [Tris(diformylamino)methane]
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- Zugänge zu Isomeren und Verwandten der Lamellarin-Alkaloide / Approach to Isomers and Structural Relatives of the Lamellarin Alkaloids
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