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Reactivity of N ‐Boc‐Protected Amino‐Ynones in the Presence of Zinc Chloride: Formation of Acetylenic Cyclic Imines and Their Palladium Complexes
Author(s) -
Vu HuyDinh,
Renault Jacques,
Roisnel Thierry,
Robert Clémence,
Jéhan Philippe,
Gouault Nicolas,
Uriac Philippe
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500569
Subject(s) - chemistry , zinc , palladium , reactivity (psychology) , lewis acids and bases , amino acid , chloride , organic chemistry , yield (engineering) , medicinal chemistry , brønsted–lowry acid–base theory , catalysis , medicine , biochemistry , materials science , alternative medicine , pathology , metallurgy
Amino‐ynones can be seen as precursors of various heterocyclic rings. Although γ‐amino‐ynones have been used to prepare exocyclic vinylogous amides in the presence of Brønsted acids, we describe here the use of zinc chloride as a weak Lewis acid for their conversion into acetylenic cyclic imines. This reaction, which was attempted for a diverse range of γ‐amino‐ynones, proved to be robust and efficient in most cases and was easily extended to δ‐amino‐ynones to yield various acetylenic cyclic imines. Depending on the workup procedure, the latter compounds could be isolated either as free organic compounds or as zinc complexes. The ability of these cyclic imines to form complexes with palladium is also reported.