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Synlett 2001; 2001(7): 1143-1145
DOI: 10.1055/s-2001-15135
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A Highly Regio- and Stereoselective Novel Route To (E)-2-Alkyl (Aryl)idene-1,2,3,4-tetrahydroquinoxalines Through a Palladium-Catalysed Arylation and Concurrent Heteroannulation Process

Rupa Mukhopadhyay* , Nitya G. Kundu
  • *Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Calcutta - 700 032, India; Fax (91) (33) 473 28 05; E-mail: ocrm@mahendra.iacs.res.in
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Publication Date:
31 December 2001 (online)

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In a single-step operation, N-(prop-2-ynyl)-N,N′-1,2-phenylene di-tosylamide 1 reacted with aryl iodides (2-11) under very mild conditions [palladium acetate (5 mol%) potassium carbonate (5 equiv.), TBAB (0.5 equiv.) in DMF at room temperature, 24 h] to yield exclusively 2-alkyl(aryl)-idene-1,4-ditosyl-1,2,3,4-tetrahydroquinoxalines 12-21 in highly satisfactory yields. Surprisingly to compounds obtained were of E-configuration instead of the usually expected Z-configuration.

quinoxalines - E-configuration - palladium catalysis