期刊
TETRAHEDRON
卷 72, 期 38, 页码 5798-5806出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.08.008
关键词
Heterocycle synthesis; Carbazole; Diels-Alder cycloaddition; Ene reaction
资金
- Newcastle University and EPSRC [EP/I033959/1]
- Umm al-Qura University
- EPSRC [EP/I033959/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/I033959/1] Funding Source: researchfish
Pentacyclic pyrrolo[3,4-a]carbazole-1,3(2H)-diones are accessed via two key synthetic steps, an intermolecular Diels-Alder (D-A) reaction between an N-protected 3-vinyl-1H-indole and N-methyl-maleimide, and a Lewis acid-catalysed intramolecular carbonyl-ene cyclisation reaction. Cyclopentyl-or cyclohexyl-containing scaffolds can be formed through variation in the length of the alkyl tether, whilst the observed stereospecificity of carbonyl-ene cyclisation supports a concerted mechanism. (C) 2016 Elsevier Ltd. All rights reserved.
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