Title:
METHOD FOR PREPARING MONOSUBSTITUTED ALKYNYLTHIACALIX[4]ARENE
Document Type and Number:
WIPO Patent Application WO/2023/104022
Kind Code:
A1
Abstract:
Disclosed is a method for preparing monosubstituted alkynylthiacalix[4]arene. The method comprises the following steps: in an inert atmosphere, feeding and blending cesium carbonate serving as a catalyst and halogenated alkyne serving as a mono-substitution reaction raw material in a thiacalix[4]arene solution for a reflux reaction, followed by purification to obtain the monosubstituted alkynylthiacalix[4]arene. The method has a high reaction efficiency, a high yield, and high selectivity.
Inventors:
JIN ZONGWEN (CN)
ZHAO JIANGLIN (CN)
XUAN SHUGUANG (CN)
ZHAO JIANGLIN (CN)
XUAN SHUGUANG (CN)
Application Number:
PCT/CN2022/136883
Publication Date:
June 15, 2023
Filing Date:
December 06, 2022
Export Citation:
Assignee:
SHENZHEN INST ADV TECH (CN)
International Classes:
C07D341/00
Foreign References:
| CN114262318A | 2022-04-01 | |||
| US6936721B2 | 2005-08-30 |
Other References:
LIU SONGYAN, YU YING-YING, ZHOU XIAO-PING, YANG XIAO-HONG: "The Research Progress of Thiacalix[4]arene in Chemical Modifications", FENZI KEXUE XUEBAO, FENZI KEXUE XUEBAO BIANJIBU, vol. 27, no. 5, 31 October 2011 (2011-10-31), pages 297 - 304, XP093072628, ISSN: 1000-9035, DOI: 10.13563/j.cnki.jmolsci.2011.05.004
WU FUYONG, YU MEI; MU LAN; ZENG XI; WANG RUI-XIAO; TAKEHIKO YAMATO: "The Ion Identification and Molecular Logic Gate of a Thiacalix [4 ]arene Fluorescent Probe", SPECTROSCOPY AND SPECTRAL ANALYSIS, BEIJING DAXUE CHUBANSHE, CN, vol. 36, no. 1, 15 January 2016 (2016-01-15), CN , pages 157 - 162, XP093072629, ISSN: 1000-0593, DOI: 10.3964/j.issn.1000-0593(2016)01-0157-06
GUO, HONGYU ET AL.: "Click Synthesis and Dye Extraction Properties of Novel Thiacalix[4]arene Derivatives with Triazolyl and Hydrogen Bonding Groups", CHINESE CHEMICAL LETTERS, vol. 24, no. 6, 30 April 2013 (2013-04-30), pages 450 - 452, XP028557793, ISSN: 1001-8417, DOI: 10.1016/j.cclet.2013.04.003
ZHU SHU-YUN, GUO HONG-YU, YANG FA-FU, WANG ZU-SHENG: "Thiacalix[4]arene 1,2,3-triazole-polyethylene glycol polymers: Synthesis and dye adsorption properties", CHINESE CHEMICAL LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 26, no. 9, 1 September 2015 (2015-09-01), AMSTERDAM, NL , pages 1091 - 1095, XP093072630, ISSN: 1001-8417, DOI: 10.1016/j.cclet.2015.03.031
LANDOVSKÝ T., DVOŘÁKOVÁ H., EIGNER V., BABOR M., KRUPIČKA M., KOHOUT M., LHOTÁK P.: "Chemoselective oxidation of phenoxathiin-based thiacalix[4]arene and the stereoselective alkylation of products", NEW JOURNAL OF CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 42, no. 24, 3 December 2018 (2018-12-03), GB , pages 20074 - 20086, XP093072632, ISSN: 1144-0546, DOI: 10.1039/C8NJ04690E
PODYACHEV, S. N. ET AL.: "New Bifunctional Compounds Obtained by Selective Hydrolysis of Tetrathiacalix[4]arene Tetraethyl Esters with Cs2CO3", TETRAHEDRON LETTERS, vol. 53, no. 25, 16 April 2012 (2012-04-16), pages 3135 - 3139, XP028488401, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2012.04.041
PARK SUN YOUNG, YOON JUNG HEE, HONG CHANG SEOP, SOUANE RACHID, KIM JONG SEUNG, MATTHEWS SUSAN E., VICENS JACQUES: "A Pyrenyl-Appended Triazole-Based Calix[4]arene as a Fluorescent Sensor for Cd 2+ and Zn 2+", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 73, no. 21, 7 November 2008 (2008-11-07), pages 8212 - 8218, XP093072634, ISSN: 0022-3263, DOI: 10.1021/jo8012918
IVAN, I. S. ET AL.: "Synthesis and Complexation Properties of 1,3-Altemate Stereoisomers of p- Tert-butylthiacalix[4]arenes Tetrasubstituted at the Lower Rim by the Phthalimide Group", MENDEDEEV COMMUNICATIONS, vol. 19, no. 4, 31 August 2009 (2009-08-31), pages 193 - 195, XP026352156, ISSN: 0959-9436
WU FUYONG, YU MEI; MU LAN; ZENG XI; WANG RUI-XIAO; TAKEHIKO YAMATO: "The Ion Identification and Molecular Logic Gate of a Thiacalix [4 ]arene Fluorescent Probe", SPECTROSCOPY AND SPECTRAL ANALYSIS, BEIJING DAXUE CHUBANSHE, CN, vol. 36, no. 1, 15 January 2016 (2016-01-15), CN , pages 157 - 162, XP093072629, ISSN: 1000-0593, DOI: 10.3964/j.issn.1000-0593(2016)01-0157-06
GUO, HONGYU ET AL.: "Click Synthesis and Dye Extraction Properties of Novel Thiacalix[4]arene Derivatives with Triazolyl and Hydrogen Bonding Groups", CHINESE CHEMICAL LETTERS, vol. 24, no. 6, 30 April 2013 (2013-04-30), pages 450 - 452, XP028557793, ISSN: 1001-8417, DOI: 10.1016/j.cclet.2013.04.003
ZHU SHU-YUN, GUO HONG-YU, YANG FA-FU, WANG ZU-SHENG: "Thiacalix[4]arene 1,2,3-triazole-polyethylene glycol polymers: Synthesis and dye adsorption properties", CHINESE CHEMICAL LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 26, no. 9, 1 September 2015 (2015-09-01), AMSTERDAM, NL , pages 1091 - 1095, XP093072630, ISSN: 1001-8417, DOI: 10.1016/j.cclet.2015.03.031
LANDOVSKÝ T., DVOŘÁKOVÁ H., EIGNER V., BABOR M., KRUPIČKA M., KOHOUT M., LHOTÁK P.: "Chemoselective oxidation of phenoxathiin-based thiacalix[4]arene and the stereoselective alkylation of products", NEW JOURNAL OF CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 42, no. 24, 3 December 2018 (2018-12-03), GB , pages 20074 - 20086, XP093072632, ISSN: 1144-0546, DOI: 10.1039/C8NJ04690E
PODYACHEV, S. N. ET AL.: "New Bifunctional Compounds Obtained by Selective Hydrolysis of Tetrathiacalix[4]arene Tetraethyl Esters with Cs2CO3", TETRAHEDRON LETTERS, vol. 53, no. 25, 16 April 2012 (2012-04-16), pages 3135 - 3139, XP028488401, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2012.04.041
PARK SUN YOUNG, YOON JUNG HEE, HONG CHANG SEOP, SOUANE RACHID, KIM JONG SEUNG, MATTHEWS SUSAN E., VICENS JACQUES: "A Pyrenyl-Appended Triazole-Based Calix[4]arene as a Fluorescent Sensor for Cd 2+ and Zn 2+", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 73, no. 21, 7 November 2008 (2008-11-07), pages 8212 - 8218, XP093072634, ISSN: 0022-3263, DOI: 10.1021/jo8012918
IVAN, I. S. ET AL.: "Synthesis and Complexation Properties of 1,3-Altemate Stereoisomers of p- Tert-butylthiacalix[4]arenes Tetrasubstituted at the Lower Rim by the Phthalimide Group", MENDEDEEV COMMUNICATIONS, vol. 19, no. 4, 31 August 2009 (2009-08-31), pages 193 - 195, XP026352156, ISSN: 0959-9436
Attorney, Agent or Firm:
BEIJING ZHONG XUN TONG DA INTELLECTUAL PROPERTY AGENCY CO., LTD. (CN)
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