| Lewis acid or Brønsted acid catalyzed reactions of vinylidene cyclopropanes with activated carbon-nitrogen, nitrogen-nitrogen, and iodine-nitrogen double-bond-containing compounds. | |
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MedLine Citation:
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PMID: 19072794 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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Lewis acid or Brønsted acid catalyzed reactions of vinylidene cyclopropanes (VDCPs), 1, with activated carbon-nitrogen, nitrogen-nitrogen, and iodine-nitrogen double-bond-containing compounds have been thoroughly investigated. We found that pyrrolidine and 1,2,3,4-tetrahydroquinoline derivatives can be formed in good yields in the reactions of VDCPs 1 with ethyl (arylimino)acetates 2 by a [3+2] cycloaddition or intramolecular Friedel-Crafts reaction pathway. Based on these results, we found that activated carbon-nitrogen and nitrogen-nitrogen double-bond-containing compounds, such as N-toluene-4-sulfonyl (N-Ts) imines 5 and diisopropylazodicarboxylate (7), can also react with VDCPs 1 to give [3+2] cycloaddition products in moderate to good yields in the presence of a Lewis acid. When N-tert-butoxycarbonyl aldimine 9 was used as the substrate, six-membered cycloaddition products 10 and 11 were formed in moderate yields in the presence of a Brønsted acid, trifluoromethanesulfonic acid (TfOH). The reactions of VDCPs 1 with N-Ts-iminophenyliodinane (12) were also carried out in the presence of (CuOTf)(2)C(6)H(6) and it was found that nitrogen-containing indene derivatives 13 were obtained, rather than the aziridination products. Plausible mechanisms for all of these transformations are discussed, based on the obtained results. |
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Authors:
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Jian-Mei Lu; Zhi-Bin Zhu; Min Shi |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Chemistry (Weinheim an der Bergstrasse, Germany) Volume: 15 ISSN: 1521-3765 ISO Abbreviation: Chemistry Publication Date: 2009 |
Date Detail:
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Created Date: 2009-01-14 Completed Date: 2009-02-24 Revised Date: 2009-08-04 |
Medline Journal Info:
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Nlm Unique ID: 9513783 Medline TA: Chemistry Country: Germany |
Other Details:
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Languages: eng Pagination: 963-71 Citation Subset: - |
Affiliation:
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State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, China. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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