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Unusual Approach to Branched 3-Alkynylamides and to 1,5-Dihydropyrrol-2-ones
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    Unusual Approach to Branched 3-Alkynylamides and to 1,5-Dihydropyrrol-2-ones
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    Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole Polytechnique, 91128 Palaiseau Cedex, France
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    Organic Letters

    Cite this: Org. Lett. 2010, 12, 3, 416–419
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    https://doi.org/10.1021/ol902472r
    Published January 12, 2010
    Copyright © 2010 American Chemical Society

    Abstract

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    Rare carboxamide branched alkynes such as 11a can be readily obtained by reaction of the electrophilic 4-alkylidene isoxazolinones with isocycanides followed by nitrosative cleavage of the heterocyclic ring. N-Iodosuccinimide induced ring closure in the presence of a nucleophile results in the formation of new iodopyrrolinones such as 16c.

    Copyright © 2010 American Chemical Society

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    Experimental procedures, full spectroscopic data and copies of 1H and 13C NMR spectra for all new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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    This article is cited by 38 publications.

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    29. Seyed Sajad Sajadikhah, Malek Taher Maghsoodlou, Nourallah Hazeri. Efficient and extremely facile one-pot four-component synthesis of mono and bis-N-aryl/alkyl-3-aminodihydropyrrol-2-one-4-carboxylates catalyzed by p-TsOH·H2O. Research on Chemical Intermediates 2015, 41 (4) , 2503-2511. https://doi.org/10.1007/s11164-013-1364-0
    30. Seyed Sajad Sajadikhah, Nourallah Hazeri, Malek Taher Maghsoodlou, Sayyed Mostafa Habibi‐Khorassani. Facile One‐pot Synthesis of Substituted Dihydropyrrol‐2‐ones via Four‐component Domino Reaction of Amines, Dialkyl Acetylenedicarboxylates and Formaldehyde. Journal of the Chinese Chemical Society 2013, 60 (8) , 1003-1006. https://doi.org/10.1002/jccs.201200597
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    34. Se-Hee Kim, Sung-Hwan Kim, Hyun-Ju Lee, Jae-Nyoung Kim. One-Pot Synthesis of 5-Hydroxypyrrolin-2-one Derivatives from Modified Morita-Baylis-Hillman Adducts via a Consecutive CuI-Mediated Aerobic Oxidation, Allylic Iodination, Hydration of Nitrile, and Lactamization. Bulletin of the Korean Chemical Society 2012, 33 (6) , 2079-2082. https://doi.org/10.5012/bkcs.2012.33.6.2079
    35. Cheol-Hee Lim, Sung-Hwan Kim, Jae-Nyoung Kim. Facile Synthesis of 5-Hydroxy-3-pyrrolin-2-ones from Morita-Baylis-Hillman Adducts. Bulletin of the Korean Chemical Society 2012, 33 (5) , 1622-1626. https://doi.org/10.5012/bkcs.2012.33.5.1622
    36. John Boukouvalas, Richard P. Loach, Etienne Ouellet. Oxidative rearrangement of 2-furylcarbamates with dimethyldioxirane: a high-yielding preparation of 5-hydroxypyrrol-2(5H)-ones. Tetrahedron Letters 2011, 52 (39) , 5047-5050. https://doi.org/10.1016/j.tetlet.2011.07.084
    37. Stefano Cicchi, Franca M. Cordero, Donatella Giomi. Five-Membered Ring Systems with O and N Atoms. 2011, 303-327. https://doi.org/10.1016/B978-0-08-096805-6.00011-5
    38. Igor Dias‐Jurberg, Fabien Gagosz, Samir Z. Zard. ChemInform Abstract: Unusual Approach to Branched 3‐Alkynylamides and to 1,5‐Dihydropyrrol‐2‐ones.. ChemInform 2010, 41 (27) https://doi.org/10.1002/chin.201027120

    Organic Letters

    Cite this: Org. Lett. 2010, 12, 3, 416–419
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol902472r
    Published January 12, 2010
    Copyright © 2010 American Chemical Society

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