![N-{3-[Benzyl(methyl)amino]propyl}-9-chloro-5,6,7,8-tetrahydro-2-acridinecarboxamide structure](https://static.chemtradehub.com/structs/142/1426944-49-1-1e4c.webp "N-{3-[Benzyl(methyl)amino]propyl}-9-chloro-5,6,7,8-tetrahydro-2-acridinecarboxamide structure")
N-{3-[Benzyl(methyl)amino]propyl}-9-chloro-5,6,7,8-tetrahydro-2-acridinecarboxamide
CAS Number:
1426944-49-1
Molecular Formula:
C25H28ClN3O
Reactivity of epoxy-ynamides with metal halides: nucleophile (Br/Cl/OH)-assisted tandem intramolecular 5-exo-dig or 6-endo-dig cyclisation and AgF2-promoted oxidation
Literature Information
Publication Date
2019-02-21
DOI
10.1039/C9QO00027E
Impact Factor
5.281
Authors
Mandala Anitha, Mallepalli Shankar, K. C. Kumara Swamy
View Original
Abstract
Several metal halides react with epoxy-ynamides. Thus, CuBr-mediated concomitant bromination/5-exo-dig cyclisation of epoxy-ynamides affords functionalised 1,3-oxazolidines. In contrast, functionalised 1,4-oxazines are obtained via 6-endo-dig cyclisation of epoxy-ynamides using LiCl or CuF2/H2O. In addition, CuBr is effective for dibromination of functionalised ynamides leading to α,β-dibromo-enamides, with the (E) isomer predominating. Formation of epoxy-1,2-dioxo-amides by oxidation of epoxy-ynamides using AgF2 as the oxidising agent is also highlighted.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
![(4aR,5S,6R,8aS)-5-[2-(3-Furyl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-3,4,4a,5,6,7,8,8a-octahydro-1-naphthalenecarboxylic acid structure](https://static.chemtradehub.com/structs/184/18411-75-1-d4cd.webp "(4aR,5S,6R,8aS)-5-[2-(3-Furyl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-3,4,4a,5,6,7,8,8a-octahydro-1-naphthalenecarboxylic acid structure")
(4aR,5S,6R,8aS)-5-[2-(3-Furyl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-3,4,4a,5,6,7,8,8a-octahydro-1-naphthalenecarboxylic acid
CAS Number:
18411-75-1
Molecular Formula:
C20H28O4
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