Synthesis of bicyclo[5.3.0]azulene derivatives.

Synthesis of bicyclo[5.3.0]azulene derivatives.
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DOI:
10.1038/nprot.2009.99
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发表时间:
2009
期刊:
影响因子:
14.8
通讯作者:
--
中科院分区:
生物学1区
文献类型:
--
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Azulene has been recognized for its application in medicinal therapy against inflammation. Recently, azulene analogs have been used in optical technology. Nevertheless, synthesis of this family of compounds is always associated with multiple challenges. In this protocol, we describe a time-efficient and cost-effective procedure for the preparation of azulene derivatives from 2-hydroxycyclohepta-2,4,6-trienone (tropolone), a readily available starting material. The technique illustrated here involves a cycloaddition reaction of a lactone with the in situ-generated vinyl ether from 2,2-dimethoxypropane during the thermolysis reaction. The three-step synthesis should take <4 d, resulting in an overall yield of 74% with a final step yield of 91%.
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