An Unusual Aminal Derivative from a Misdirected Gabriel Synthesis
- 1 July 1985
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 15 (9) , 837-841
- https://doi.org/10.1080/00397918508063879
Abstract
N-(2-Bromoethyl)phthalimide (1) was reacted with sodium imidazolate in DMF to give the novel aminal N-[1-(1H-imidazol-1-yl)ethyl]phthalimide (4a) as well as N-vinylphthalimide (3) and the desired Gabriel intermediate 2. Aminal 4a as well as heterologues 4b - d form directly from reaction of 3 with the appropriate heterocyclic sodium salt.Keywords
This publication has 7 references indexed in Scilit:
- Homogenkatalytische Vinylierung von cyclischen Imiden und Lactamen zur Synthese vonN-VinylmonomerenAngewandte Chemie, 1979
- Synthesis of Bi‐ and tridentate imidazole ligandsJournal of Heterocyclic Chemistry, 1977
- Five-membered rings. II. Inter and intramolecular reactions of simple amines with N-substituted phthalimides. Methylamine as a reagent for removal of a phthaloyl group from nitrogenCanadian Journal of Chemistry, 1970
- The Gabriel Synthesis of Primary AminesAngewandte Chemie International Edition in English, 1968
- Synthesis of N-VinylphthalamidesNippon kagaku zassi, 1962
- Reaction of Vinyl Ethers with Acidic Imino Compounds. A New Synthesis of Some N-Vinyl ImidesThe Journal of Organic Chemistry, 1958
- Notiz über ein N‐substituiertes PyrrolEuropean Journal of Inorganic Chemistry, 1951