Diels-alder reactions of 3-(2-nitrovinyl)indoles: Formation of carbazoles and bridged carbazoles
β Scribed by Wayland E. Noland; Michael J. Konkel; Michael S. Tempesta; Russell D. Cink; Dawn M. Powers; Elmer O. Schlemper; Charles L. Barnes
- Book ID
- 112130566
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1993
- Tongue
- English
- Weight
- 702 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0022-152X
No coin nor oath required. For personal study only.
π SIMILAR VOLUMES
## Abstract 3βIndolylalkanoic acids 2 react with benzoic acid anhydride under catalysis of Et~2~O β ZnCl~2~ and mild conditions to furnish the 1βphenylβsubstituted pyrano[3,4β__b__]indolβ3βones 1c, 1d, and 3a, 3b. Products 1c, 1d, and 3b may be converted into the novel functionalized carbazoles 4 a
The role of the substitution pattern on the stability of the obtained 1.2-dihydreearbazolee is interpreted In terms of electronic and steric effects on the aromatization to the corresponding carbazoles. CH and 2-CHb bonds, a small coupling constant of 1,6 Hz is observed. A dihedral angle of about 26