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One-step conversion of 3,4-dichlorocoumarins to 3-chloroflavones

โœ Scribed by Melvin S. Newman; John L. Ferrari

Book ID
104212515
Publisher
Elsevier Science
Year
1962
Tongue
French
Weight
110 KB
Volume
3
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

ON treatment with phenylmagnesium bromide the 3,4-dichlorocoumarins,' I, are converted into the corresponding 3-chlorofle,ones, II. This is apparently the first instance of a one-step conversion of the coumarin system into the flavone system. 2 In previous studies involving treatment of coumarins with Grignard reagents chromenes, chromenols, chromanols and benzopyrylium salts have been obtained.3 Since the 3,4-dichlorocoumarins, I, are prepared in one step from phenols and hexachloropropene,' a two-step synthesis of 3-chloroflavones, II, from phenols is at hand. Cl 0 CbH&fgBr Ia (R=R~=H) b (R=cH,, R'=H) c (R=Cl, R'=H) d (R=CH~, R'=CO~H~) II

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