154124-86-4Relevant academic research and scientific papers
Diels-Alder Reactions of 3-(2-nitrovinyl)indoles: Formation of Carbazoles and Bridged Carbazoles
Noland, Wayland E.,Konkel, Michael J.,Tempesta, Michael S.,Cink, Russell D.,Powers, Dawn M.,et al.
, p. 183 - 192 (2007/10/02)
The Diels-Alder reactions of 1-substituted-3-(2-nitrovinyl)indoles 3 with quinones and acetylenes give aromatized 1:1 adducts (- nitrous acid) (1) or (- nitrous acid, -2 hydrogens) 2,5.Likewise, dimerization (-2 nitrous acids) of 3 gives aromatized 2-(3-indolyl)carbazoles 4.In contrast, 3 reacts with maleimides 6 to give 1:2 adducts (-nitrous acid or -2hydrogens) 10 and 11, respectively, along with smaller amounts of 1:1 adducts (- nitrous acid, -2 hydrogens; or -4 hydrogens) 12 and 13, respectively.A mechanism for formation of the nitro products 11 and 13 is discussed.A 1:2 adduct (-2 hydrogens) 19 was also obtained from a Diels- Alder reaction between maleimide and the vinylindole produced in situ by condensing 1-methylindole with acetone.The stereochemistry of this 1:2 adduct has been determined by X-ray crystallography.
