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Title
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The use of calcium carbide as acetylene source in a three-component coupling with omega-chlorinated ketones and primary amines
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Author
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Abstract
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| Calcium carbide was used in a Cu-I-catalysed three-component coupling with omega-chlorinated ketones and primary amines to generate terminal 2-alkynyl-N-heterocycles. The formation of an imine and the subsequent intramolecular substitution results in an active electrophilic iminium species, which can be alkynylated by in situ formed copper acetylide. A number of aliphatic primary (functionalised) amines and aliphatic or aromatic alkynes together with different alkyl- or aryl-substituted gamma- or delta-chloroketones could be used. Simple acid-base workup instead of column chromatography can be applied to obtain the resulting 2-alkynylpyrrolidines and 2-alkynylpiperidines. |
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Language
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English
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Source (journal)
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Chemistry: a European journal. - Weinheim
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Publication
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Weinheim
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2018
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ISSN
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0947-6539
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DOI
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10.1002/CHEM.201803669
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Volume/pages
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24
:62
(2018)
, p. 16645-16651
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ISI
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000449551100024
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Pubmed ID
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30112778
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Full text (Publisher's DOI)
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Full text (open access)
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Full text (publisher's version - intranet only)
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