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Reaction of some substituted 2-allylphenols with 2,3-dichloro-5, 6-dicyano-1,4-benzoquinone (DDQ) - a new method for the synthesis of coumarins

✍ Scribed by K.V. Subba Raju; G. Srimannarayana; N.V. Subba Rao

Publisher: Elsevier Science
Year: 1977
Tongue: French
Weight: 234 KB
Volume: 18
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)92669-3

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✦ Synopsis

Several methods are available for the synthesis of coumarin ring systeml. We nQy report a new method for the synthesis of coumarins by oxidative cyclisation of some substituted 2allylphenols by 2,3=dichloro-5,6-dicyano-1,4-bensoguinone 0).

7-Allyloxy-3-methylflavone2 on Claisen rearrangement b vacua at 18QQ yielded 7-hydroxy-8-allyl-3-methylflavone (Ib) m.p. 229-30° (95% yield). Ib (0.001 mole) and DDQ (0.003 mole) in benzene were refluxed for 16 hours.

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