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Volumn , Issue 15, 2011, Pages 2167-2170

Copper(II)-catalyzed synthesis of pyrazinones from α-Azido-N- allylamides under an oxygen atmosphere

Author keywords

1,3 dipolar cycloaddition; copper; organic azides; oxygen; pyrazinone

Indexed keywords

2 FORMYL PYRAZINONE DERIVATIVE; ALKENE; ALPHA AZIDO N ALLYLAMIDE; AZIRIDINE DERIVATIVE; CUPRIC ION; PYRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 80052675780     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1261185     Document Type: Article
Times cited : (9)

References (40)
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    • For recent reports on the bioactivity study of substituted pyrazines and their derivatives, see
    • For recent reports on the bioactivity study of substituted pyrazines and their derivatives, see
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    • 4 and NaOAc exhibited similar reactivity, while MgO was not a viable catalyst for this transformation.
    • 4 and NaOAc exhibited similar reactivity, while MgO was not a viable catalyst for this transformation.
  • 22
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    • The structures of 3b and 3i were secured by X-ray crystallographic analysis (see Supporting Information). The supplementary crystallographic data of these molecules are contained in CCDC 824717 and 824717, respectively. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/conts/retrieving.html.
    • The structures of 3b and 3i were secured by X-ray crystallographic analysis (see Supporting Information). The supplementary crystallographic data of these molecules are contained in CCDC 824717 and 824717, respectively. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/conts/retrieving.html.
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    • Dihydropyrazinone 4 might be formed from the proposed primary alkyl radical D (in Scheme 7) by hydrogen abstraction from the solvent DMF. For the process of hydrogen abstraction from the solvent DMF
    • Dihydropyrazinone 4 might be formed from the proposed primary alkyl radical D (in Scheme 7) by hydrogen abstraction from the solvent DMF. For the process of hydrogen abstraction from the solvent DMF:, Minisci F, Citterio A, Vismara E, Giordano C, Tetrahedron 1985 41 4157
    • (1985) Tetrahedron , vol.41 , pp. 4157
    • Minisci, F.1    Citterio, A.2    Vismara, E.3    Giordano, C.4
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    • For generation of imine from -azido ketones and esters under the strong basic conditions, see
    • For generation of imine from -azido ketones and esters under the strong basic conditions, see:, Manis P A., Rathke M W., J. Org. Chem. 1980 45 4952
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    • One of the possibilities of the reaction course for the formation of deallylated amide 7 is outlined below. It might commence with radical 1,5-H shift from putative iminyl copper species to give allylic radical, further oxidation of which would afford allylic cation species. Addition of water to the carbocation followed by C-N bond cleavage from resulting hemiaminal could deliver deallylated amide 7 (Scheme 8). We recently reported similar 1,5-H shift from iminyl copper species, see
    • One of the possibilities of the reaction course for the formation of deallylated amide 7 is outlined below. It might commence with radical 1,5-H shift from putative iminyl copper species to give allylic radical, further oxidation of which would afford allylic cation species. Addition of water to the carbocation followed by C-N bond cleavage from resulting hemiaminal could deliver deallylated amide 7 (Scheme 8). We recently reported similar 1,5-H shift from iminyl copper species, see:, Zhane L, Ang G Y., Chiba S, Org. Lett. 2011 13 1622
    • (2011) Org. Lett. , vol.13 , pp. 1622
    • Zhane, L.1    Ang, G.Y.2    Chiba, S.3
  • 28
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    • For recent reports on the azido-alkene 1,3-dipolar cycloaddition reaction, see
    • For recent reports on the azido-alkene 1,3-dipolar cycloaddition reaction, see:, Hui B W.-Q, Chiba S, Org. Lett. 2009 11 729
    • (2009) Org. Lett. , vol.11 , pp. 729
    • Hui, B.W.-Q.1    Chiba, S.2
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    • For reports on the mechanism of the elimination of dinitrogen from triazoline intermediates with heterolytic cleavage of the N-N bond, see
    • For reports on the mechanism of the elimination of dinitrogen from triazoline intermediates with heterolytic cleavage of the N-N bond, see:, Shea K J., Kim J.-S, [nl]J. Am. Chem. Soc. 1992 114 4846
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    • A radical pathway via homolytic cleavage of the N-N bond of triazoline intermediates is proposed, see
    • A radical pathway via homolytic cleavage of the N-N bond of triazoline intermediates is proposed, see:, Broeckx W, Overbergh N, Samyn C, Smets G, Labbé G, Tetrahedron 1971 27 3527
    • (1971) Tetrahedron , vol.27 , pp. 3527
    • Broeckx, W.1    Overbergh, N.2    Samyn, C.3    Smets, G.4    Labbé, G.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.