Title:
ONE-STEP SYNTHESIS METHOD FOR POLYSUBSTITUTED CYCLOHEX-2-ENONE
Document Type and Number:
WIPO Patent Application WO/2022/016743
Kind Code:
A1
Abstract:
A one-step synthesis method for a polysubstituted cyclohex-2-enone, where a terminal alkyne, a ketone, and ethyl acetoacetate are used as reaction raw materials, a reaction is formed in a polar aprotic solvent and in the presence of a strong base, and a polysubstituted cyclohex-2-enone is obtained. The present method utilizes inexpensive materials, is simple to perform, takes little time, has a broad substrate scope, a precious metal catalyst is not needed in the reaction process, and 3, 4, 5-position substituents of the cyclohex-2-enone can further be freely adjusted by means of terminal alkyne and ketone types.
Inventors:
ZHANG ZHIHUA (CN)
JIANG DAHONG (CN)
WANG XU (CN)
LI LEI (CN)
SUN JING (CN)
ZHANG GUIXI (CN)
BAO LIN (CN)
JIANG DAHONG (CN)
WANG XU (CN)
LI LEI (CN)
SUN JING (CN)
ZHANG GUIXI (CN)
BAO LIN (CN)
Application Number:
PCT/CN2020/127129
Publication Date:
January 27, 2022
Filing Date:
November 06, 2020
Export Citation:
Assignee:
UNIV GUANGDONG PETROCHEM TECH (CN)
International Classes:
C07C49/657; C07C45/74; C07C49/67; C07C49/697; C07C49/753
Foreign References:
| JP2005206549A | 2005-08-04 | |||
| CN106414377A | 2017-02-15 |
Other References:
KIM, B.T. MIN, Y.K. ASAMI, T. PARK, N.K. JEONG, I.H. CHO, K.Y. YOSHIDA, S.: "Synthesis and biological activities of new fluorinated abscisic acid", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 5, no. 3, 2 February 1995 (1995-02-02), AMSTERDAM, NL , pages 275 - 278, XP004819361, ISSN: 0960-894X, DOI: 10.1016/0960-894X(95)00014-K
FRACKENPOHL JENS, GRILL ERWIN, BOJACK GUIDO, BALTZ RACHEL, BUSCH MARCO, DITTGEN JAN, FRANKE JANA, FREIGANG JÖRG, GONZALEZ SUSANA, : "Insights into the in Vitro and in Vivo SAR of Abscisic Acid - Exploring Unprecedented Variations of the Side Chain via Cross-Coupling-Mediated Syntheses : Insights into the in Vitro and in Vivo SAR of Abscisic Acid - Exploring Unprecedented Variations of the Side Chain via Cross-Coupling-Mediated Sy", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 2018, no. 12, 29 March 2018 (2018-03-29), DE , pages 1403 - 1415, XP055888978, ISSN: 1434-193X, DOI: 10.1002/ejoc.201701687
NIE JING, JIANG DAHONG: "Morpholine Promoted One-pot Synthesis of 3-Methyl-5-phenylcyclohex-2-enone", JOURNAL OF GUANGDONG UNIVERSITY OF PETROCHEMICAL TECHNOLOGY., vol. 28, no. 3, 15 June 2018 (2018-06-15), pages 45 - 48, XP055889002, ISSN: 2095-2562
M. G. AHMED, S. A. AHMED, U. K.R. ROMMAN, K. AKHTER, M. A. CHOWDHURY, F. KIUCHI: "Synthesis of substituted cyclohex-2-enones", INDIAN JOURNAL OF CHEMISTRY - SECTION B ORGANIC AND MEDICINAL CHEMISTRY, vol. 40, no. 8, 31 August 2001 (2001-08-31), DE , pages 710 - 712, XP009533607, ISSN: 0376-4699
FRACKENPOHL JENS, GRILL ERWIN, BOJACK GUIDO, BALTZ RACHEL, BUSCH MARCO, DITTGEN JAN, FRANKE JANA, FREIGANG JÖRG, GONZALEZ SUSANA, : "Insights into the in Vitro and in Vivo SAR of Abscisic Acid - Exploring Unprecedented Variations of the Side Chain via Cross-Coupling-Mediated Syntheses : Insights into the in Vitro and in Vivo SAR of Abscisic Acid - Exploring Unprecedented Variations of the Side Chain via Cross-Coupling-Mediated Sy", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 2018, no. 12, 29 March 2018 (2018-03-29), DE , pages 1403 - 1415, XP055888978, ISSN: 1434-193X, DOI: 10.1002/ejoc.201701687
NIE JING, JIANG DAHONG: "Morpholine Promoted One-pot Synthesis of 3-Methyl-5-phenylcyclohex-2-enone", JOURNAL OF GUANGDONG UNIVERSITY OF PETROCHEMICAL TECHNOLOGY., vol. 28, no. 3, 15 June 2018 (2018-06-15), pages 45 - 48, XP055889002, ISSN: 2095-2562
M. G. AHMED, S. A. AHMED, U. K.R. ROMMAN, K. AKHTER, M. A. CHOWDHURY, F. KIUCHI: "Synthesis of substituted cyclohex-2-enones", INDIAN JOURNAL OF CHEMISTRY - SECTION B ORGANIC AND MEDICINAL CHEMISTRY, vol. 40, no. 8, 31 August 2001 (2001-08-31), DE , pages 710 - 712, XP009533607, ISSN: 0376-4699
Attorney, Agent or Firm:
GUANGZHOU RUNHE INTELLECTUAL PROPERTY AGENCY (GENERAL PARTNERSHIP) (CN)
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