Title:
METHOD FOR PREPARING 2-(CYCLOHEXENYLENE) MALONIC ACID DERIVATIVE AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2018/120094
Kind Code:
A1
Abstract:
Provided are a method for preparing a 2-(cyclohexenylene) malonic acid derivative and the use thereof. In the method, an olefin and a 2-substituted malonic acid derivative are used as raw materials and are subjected to a cyclization reaction in the presence of a catalyst so as to give the 2-(cyclohexenylene) malonic acid derivative. The method has the following features: (1) same is capable of synthesizing a 2-(2,6-disubstituted cyclohexenylene) malonic acid derivative very efficiently; and (2) same has a high reaction yield, mild conditions, less of the three wastes, and is favourable for industrial production. More importantly, the 2-(cyclohexenylene) malonic acid derivative can be used in organic synthesis, and in particular, can be used in the synthesis of 2-aryl malonic acid derivatives and the corresponding drugs, such as the herbicide pinoxaden.
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Inventors:
SUN YINWEI (CN)
WANG ZHONGYUAN (CN)
ZHANG PAN (CN)
CHEN BANGCHI (CN)
WANG ZHONGYUAN (CN)
ZHANG PAN (CN)
CHEN BANGCHI (CN)
Application Number:
PCT/CN2016/113671
Publication Date:
July 05, 2018
Filing Date:
December 30, 2016
Export Citation:
Assignee:
ORIENTAL LUZHOU AGROCHEMICALS CO LTD (CN)
International Classes:
C07C69/38; A01N43/90; A01P13/00; C07C13/20; C07C67/22
Domestic Patent References:
| WO2011098398A1 | 2011-08-18 |
Foreign References:
| CN102336686A | 2012-02-01 | |||
| CN103804232A | 2014-05-21 | |||
| CN1355806A | 2002-06-26 |
Other References:
APSIMON, J.W. ET AL.: "Potassium Fluoride Catalysed Reactions between M alononitrile and a, beta-unsaturated Ketones", CANADIAN JOURNAL OF CHEMISTRY, vol. 48, no. 19, 31 October 1970 (1970-10-31), pages 3064 - 3075, XP055509763
MA, CHAO ET AL.: "supporting information: A Concise Assembly of Electron-Deficient 2, 4-Dienes and 2, 4-Dienals: Regio-and Stereoselective Exo-Diels-Alder and Redox Reactions through Sequential Amine and Carbene Catalysis", ANGEWANDTE CHEMIE, December 2012 (2012-12-01), pages S3 - S5, XP055509779
PARK, D.Y. ET AL.: "Regioselective Synthesis of Pentasubstituted Benzene Derivatives: TBAF as an Effective Catalyst for the Sequential Michael Addition-intramolecular Aldolization", TETRAHEDRON LETTERS, vol. 47, no. 37, 28 July 2006 (2006-07-28), pages 6641 - 6645, XP025004835
BARINELLI, L.S. ET AL.: "Deprotonation of the Adducts of fS-Dicarbonyl Anions and [(14-Diene) Co(CO)3]BF4", ORGANOMETALLICS, vol. 8, no. 10, 4 April 1989 (1989-04-04), pages 2474 - 2476, XP055509793
VOLCHO, K.P. ET AL.: "Competing Michael and Knoevenagel Reactions of Terpenoids with Malononitrile on Basic Cs-beta Zeolite", JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL, vol. 195, no. 1-2, 18 October 2002 (2002-10-18), pages 263 - 274, XP055509799
J. MOL. CATA. A. CHEM., vol. 195, no. 1-2, 2003, pages 263
ORGANOMETALLICS, vol. 8, no. 10, 1989, pages 2474
TETRAHEDRON, vol. 70, no. 13, 2014, pages 2257 - 2263
EUR. J. MED. CHEM., vol. 85, 2014, pages 450 - 457
See also references of EP 3564208A4
MA, CHAO ET AL.: "supporting information: A Concise Assembly of Electron-Deficient 2, 4-Dienes and 2, 4-Dienals: Regio-and Stereoselective Exo-Diels-Alder and Redox Reactions through Sequential Amine and Carbene Catalysis", ANGEWANDTE CHEMIE, December 2012 (2012-12-01), pages S3 - S5, XP055509779
PARK, D.Y. ET AL.: "Regioselective Synthesis of Pentasubstituted Benzene Derivatives: TBAF as an Effective Catalyst for the Sequential Michael Addition-intramolecular Aldolization", TETRAHEDRON LETTERS, vol. 47, no. 37, 28 July 2006 (2006-07-28), pages 6641 - 6645, XP025004835
BARINELLI, L.S. ET AL.: "Deprotonation of the Adducts of fS-Dicarbonyl Anions and [(14-Diene) Co(CO)3]BF4", ORGANOMETALLICS, vol. 8, no. 10, 4 April 1989 (1989-04-04), pages 2474 - 2476, XP055509793
VOLCHO, K.P. ET AL.: "Competing Michael and Knoevenagel Reactions of Terpenoids with Malononitrile on Basic Cs-beta Zeolite", JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL, vol. 195, no. 1-2, 18 October 2002 (2002-10-18), pages 263 - 274, XP055509799
J. MOL. CATA. A. CHEM., vol. 195, no. 1-2, 2003, pages 263
ORGANOMETALLICS, vol. 8, no. 10, 1989, pages 2474
TETRAHEDRON, vol. 70, no. 13, 2014, pages 2257 - 2263
EUR. J. MED. CHEM., vol. 85, 2014, pages 450 - 457
See also references of EP 3564208A4
Attorney, Agent or Firm:
HANGZHOU QIUSHI PATENT OFFICE CO.,LTD. (CN)
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