Title:
PRODUCTION OF NAPHTHOQUINONE DERIVATIVE AND INTERMEDIATE THEREOF
Document Type and Number:
Japanese Patent JP3276246
Kind Code:
B2
Abstract:
PURPOSE: To obtain a derivative which is important as a hematostasis-activating vitamin without formation of its geometric isomer, in high yield and in an industrial scale by the reverse Diels-Alder reaction of a specific anthraquinone derivative.
CONSTITUTION: 1,4,4a,5,8,9-Hexahydro-4aα-alkenyl-1α,4α-methanoanthraquinone of formula I (R1, R2 are H, methyl; n is 0, 1 to 9; formula II is a single bond or a double bond) is subjected to reverse Diels-Alder reaction in the presence of a dehydrogenating agent or an oxidizing agent to give the object derivative of formula III. A compound which is obtained by reacting, in the presence of a base, an allyl derivative of formula VI with a derivative of formula V which is a product from Dilels-Alder reaction of a derivative of formula IV with cyclopentadiene is preferably used as the derivative of formula I. Further, the dehydrogenating agent is preferably 2,3-dichloro-5,6-dicyano-1,4-benzoquinone or p- or o-chloranyl, while the oxidizing agent is manganese dioxide.
Inventors:
Kichisaburo Hamamura
Chiaki Seki
Yuusuke Konishi
Chiaki Seki
Yuusuke Konishi
Application Number:
JP17300594A
Publication Date:
April 22, 2002
Filing Date:
July 26, 1994
Export Citation:
Assignee:
Eisai Co., Ltd.
International Classes:
C07C46/00; C07C50/14; C07C50/22; (IPC1-7): C07C50/14; C07C46/00; C07C50/22
Domestic Patent References:
| JP6056935A | ||||
| JP6312950A |
Other References:
Ｄｅｋｋｅｒ，Ｊ．，ｅｔ．ａｌ．，，Ｂｉｒｄ−ｃａｇｅ ｃｏｍｐｏｕｎｄｓ．Ｐａｒｔ ▲ＩＩ▼．，Ｊ．Ｓ．Ａｆｒ．Ｃｈｅｍ．Ｉｎｓｔ．，Ｖｏｌ．２９，Ｎｏ．２（１９７６），１１４−１１９
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