![N-[4-(Cyanoethynyl)phenyl]-16-oxo-4,7,10,13-tetraoxa-17-azahenicos-1-yn-21-amide structure](https://static.chemtradehub.com/structs/218/2183440-36-8-68cb.webp "N-[4-(Cyanoethynyl)phenyl]-16-oxo-4,7,10,13-tetraoxa-17-azahenicos-1-yn-21-amide structure")
N-[4-(Cyanoethynyl)phenyl]-16-oxo-4,7,10,13-tetraoxa-17-azahenicos-1-yn-21-amide
CAS Number:
2183440-36-8
Molecular Formula:
C25H31N3O6
Iodine mediated oxidative cross-coupling of unprotected anilines and heteroarylation of benzothiazoles with 2-methylquinoline
Literature Information
Publication Date
2017-12-19
DOI
10.1039/C7OB02241G
Impact Factor
3.876
Authors
Abdullah Alarifi
View Original
Abstract
Iodine-promoted oxidative C–H/C–H cross-coupling of unprotected anilines and 2-methylquinoline to furnish C4-carbonylated aniline (4-aminophenyl)(quinoline-2-yl) methanones in moderate to good yields has been demonstrated. This work provides the first site-selective approach for the synthesis of free amino groups containing methanones including unprecedented C–H functionalization rather than the N–H functionalization of unprotected anilines via the Kornblum oxidation of 2-methylquinoline. Furthermore, we noticed that the incorporation of KOH under standard conditions provides 2-heteroarylbenzothiazoles from benzothiazoles and 2-methylquinoline in good to excellent yields. These transformations do not require any transition metals or peroxides and tolerate various functional groups such as methoxy, hydroxy, bromo, chloro and nitro groups. Moreover, a plausible mechanistic pathway is proposed.
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
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methyl 6-bromo-3-formyl-1H-indole-4-carboxylate
CAS Number:
1353636-63-1
Molecular Formula:
C11H8BrNO3
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4,4-Difluoro-2-methyl-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-proline
CAS Number:
1194032-23-9
Molecular Formula:
C11H17F2NO4
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