2011
DOI: 10.1016/j.tet.2011.08.030
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4-Chloro-3-(trifluoroacetyl)- and 4-chloro-3-(methoxalyl)coumarins as novel and efficient building blocks for the regioselective synthesis of 3,4-fused coumarins

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Cited by 42 publications
(34 citation statements)
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“…Compounds with basic coumarin skeleton ring structure reduce trauma or disease-induced tissue inflammation due to their antioxidant, anti-inflammatory and immunosuppressive activities [5].…”
Section: Introductionmentioning
confidence: 99%
“…Compounds with basic coumarin skeleton ring structure reduce trauma or disease-induced tissue inflammation due to their antioxidant, anti-inflammatory and immunosuppressive activities [5].…”
Section: Introductionmentioning
confidence: 99%
“…Our starting point was the development of suitable conditions for the synthesis of pyrido[3,2‐ c ]coumarin 3a by reaction of chromone‐3‐carboxylic acid 1a with aminopyrazole 2a (Scheme ). The aminopyrazole 2a and related aminoheterocycles used in this study were prepared as previously reported in our work related to the synthesis of heteroannulated pyridines, spirocyclic 1,4‐dihydropyridine compounds, and 3,4‐fused coumarins . The best yield of 3a (up to 90 %) was obtained under the conditions reported in entry 5 of Table using acetic acid as solvent (14 h, 60 °C).…”
Section: Resultsmentioning
confidence: 89%
“…This transformation can be rationalized by assuming the initial formation of intermediate 11Ј accompanied by intramolecular nucleophilic addition of the hydroxyl group at the triple bond (Scheme 4). We also hoped to increase the scope of this reaction to include 3-(trifluoroacetyl)chromone [25] and 4-chloro-3-(trifluoroacetyl)coumarin, [26] however, these attempts were unsuccessful. Previously, alkynyl ketones have been condensed with amidines to give pyrimidines.…”
Section: Resultsmentioning
confidence: 99%