Reaction of N-sulfonyl-1,4-benzoquinone imines with enamines View Full Text


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Article Info

DATE

2017-04

AUTHORS

S. A. Konovalova, A. P. Avdeenko, V. V. Pirozhenko, A. L. Yusina, G. V. Palamarchuk, S. V. Shishkina

ABSTRACT

N-Sulfonyl derivatives of 1,4-benzoquinone imine reacted with enamines to give 1,4-addition products and products of their subsequent cyclization, substituted 5-aminobenzofurans and 5-aminoindoles, depending on the solvent nature, electron-withdrawing power of the substituent on the quinone imine nitrogen atom, and enamine structure. The presence of strong electron-withdrawing trifluoromethanesulfonyl group on the quinone imine nitrogen atom favors formation of 1,4-addition products and benzofuran derivatives. More... »

PAGES

525-538

References to SciGraph publications

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  • 2006-05. Halogenation of N-substituted para-quinone monoimine and para-quinone monooxime esters: V. Chlorination and bromination of N-arylsulfonyl-1,4-benzoquinone monoimines dialkyl-substituted in the quinoid ring in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • 1974-11. Synthesis of 5-aminoindole derivatives from N-arylsulfonylquinone diimines in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
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  • 2005-07. Quinoneimines in the Nenitzescu reaction in RUSSIAN CHEMICAL BULLETIN
  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1134/s1070428017040054

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    http://dx.doi.org/10.1134/s1070428017040054

    DIMENSIONS

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