- One-step synthesis of dialkynyl-1,2-diones and their conversion to fused pyrazines bearing enediyne units
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A convenient procedure for the preparation of symmetrically end-protected dialkynyl-1,2-diones 3 from lithium acetylides and oxalyl chloride in the presence of CuBr and LiBr is described. The condensation of 3 with various aromatic and heteroaromatic 1,2-diamines leads to pyrazine-based α-dialkynylated heterocycles. The enediyne substructure of diethynylquinoxaline can be thermally rearranged in a Bergman cyclization reaction.
- Faust, Ruediger,Weber, Christian,Fiandanese, Vito,Marchese, Giuseppe,Punzi, Angela
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- 1,2-dialkinylated compounds
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PCT No. PCT/EP97/03340 Sec. 371 Date May 20, 1998 Sec. 102(e) Date May 20, 1998 PCT Filed Jun. 25, 1997 PCT Pub. No. WO98/00386 PCT Pub. Date Jan. 8, 1998The present invention is relative to 1,2-dialkynylated compounds, especially dialkynyl-1,2-diones, a
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- Terminally protected 1-phenyl-1,5-hexadiyne-3,4-diones as first members of the class of dialkynyl-1,2-diones
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Reaction of lithiated 1-(1-ethoxy-3-phenyl-prop-2-ynyl)-1H-benzotriazole (3) with various acetylenic aldehydes followed by periodinane oxidation and hydrolysis yields terminally protected 1-phenyl-1,5-hexadiyne-3,4-diones 7a-d as the first examples of dialkynyl-1,2-diones. VCH Verlagsgesellschaft mbH, 1996.
- Faust, Ruediger,Weber, Christian
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p. 1235 - 1238
(2007/10/03)
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