A novel and facile synthesis of 7,8-diacylcoumarins

Tetrahedron Letters

Volumn 48, Issue 40, 2007, Pages 7181-7183

  Kotali, Antigoni ^a   Lafazanis, Ioannis S ^a   Harris, Philip A ^b  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^b GLAXOSMITHKLINE   (United States)

Author keywords

7,8 Diacylcoumarins; Lead tetraacetate; N Acylhydrazones; Transformation

Indexed keywords

7,8 DIACYLCOUMARIN DERIVATIVE; COUMARIN; FUNCTIONAL GROUP; HYDRAZONE DERIVATIVE; HYDROXYL GROUP; UMBELLIFERONE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DRUG SYNTHESIS; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 34548455393     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.202     Document Type: Article

References (17)

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16. Preparation of 7-hydroxy-8-acetylcoumarin N-carbonylhydrazones (4). A mixture of 7-hydroxy-8-acetylcoumarin 3 (5 mmol) and the corresponding hydrazide, in the molar ratio 1:1 were refluxed in propanol (20 ml), for 24 h. The mixture was allowed to cool and the resulting precipitate was filtered and subsequently dried to afford the pure products 4 as white solids (Tables 1 and 2).
17. Preparation of 7,8-diacylcoumarins 5. Lead tetracetate was added to a stirred solution of hydrazone 4 (1 mmol) in THF (20 ml), in an ice bath. The molar ratios of hydrazone/LTA and the reaction times are presented in Table 1. The mixture was then stirred at rt with the exception of 4f, which was stirred in an ice bath. The oily product obtained after filtration of lead diacetate and condensation of the filtrate was subjected to column chromatography (silica gel 70-230 mesh) eluting with a mixture of petroleum ether/ethyl acetate 1:1 to afford pure products 5 as white solids (Tables 1 and 2).