![4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxy-6-quinazolinyl acetate structure](https://static.chemtradehub.com/structs/740/740081-22-5-f58f.webp "4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxy-6-quinazolinyl acetate structure")
4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxy-6-quinazolinyl acetate
CAS Number:
740081-22-5
Molecular Formula:
C17H13ClFN3O3
(E)-Selective Friedel–Crafts acylation of alkynes to β-chlorovinyl ketones: defying isomerizations in batch reactions by flow chemistry approaches
Literature Information
Publication Date
2019-04-11
DOI
10.1039/C9QO00217K
Impact Factor
5.281
Authors
Hyungmo Koo, Hun Young Kim, Kyungsoo Oh
View Original
Abstract
The Friedel–Crafts acylation of alkynes stereoselectively provides (Z)-β-chlorovinyl ketones, whereas the AlCl3-promoted reaction yields a mixture of stereoisomeric β-chlorovinyl ketones. To develop the (E)-selective synthesis of β-chlorovinyl ketones, a flow chemistry approach was devised for the Friedel–Crafts acylation of alkynes that defies the facile (E) → (Z) isomerization under the AlCl3-promoted reaction conditions. Compared to batch reactions, the flow chemistry approach provides a fast, clean, high yielding, and stereoselective synthetic route to (E)-β-chlorovinyl ketones.
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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
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