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- Title
The Annelation for Enaminoureides of 3,3-Dimethyl-1,2,3,4-tetrahydroisoquinoline Series by Action of Oxalyl Chloride and Ninhydrin.
- Authors
Mikhailovskii, A. G.; Yusov, A. S.; Korchagin, D. V.; Gashkova, O. V.
- Abstract
By reaction of Ritter cyclization of cyanoacetylureas with dimethylbenzylcarbinoles the corresponding enaminoureides were obtained, derivatives of 3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline. The polyfunctional character of obtained compounds is confirmed by the structure of products of reaction with some electrophiles: phenyl isocyanate reacts at the γ-C atom of enamine and CONH2 group of urea, under the action of oxalyl chloride annelation of a pyrrole cycle occurs with the formation of a derivative of 2,3-dioxopyrrolo[2,1-a]isoquinoline. Reaction with ninhydrin occurs similary with enaminoamides having hydrogen atoms at the amide nitrogen: a pyrrole ring is fused with the formation of a system of indeno[1,2-b]pyrrole.
- Subjects
OXALYL chloride; ETHANES; ENAMINES; TETRAHYDROISOQUINOLINES; PYRROLES; ELECTROPHILES
- Publication
Russian Journal of Organic Chemistry, 2018, Vol 54, Issue 5, p713
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S107042801805007X