CN108314658A - 一种多取代噁唑衍生物的制备方法 - Google Patents
一种多取代噁唑衍生物的制备方法 Download PDFInfo
- Publication number
- CN108314658A CN108314658A CN201810326839.2A CN201810326839A CN108314658A CN 108314658 A CN108314658 A CN 108314658A CN 201810326839 A CN201810326839 A CN 201810326839A CN 108314658 A CN108314658 A CN 108314658A
- Authority
- CN
- China
- Prior art keywords
- substituted
- phenyl
- duo
- preparation
- derivative
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000002916 oxazoles Chemical class 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- -1 phenoxy group amides Chemical class 0.000 claims abstract description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 8
- 239000012043 crude product Substances 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000011630 iodine Substances 0.000 claims abstract description 4
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 238000006467 substitution reaction Methods 0.000 claims abstract description 4
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 3
- 238000000926 separation method Methods 0.000 claims abstract 2
- 238000003756 stirring Methods 0.000 claims abstract 2
- 150000007978 oxazole derivatives Chemical class 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 238000000034 method Methods 0.000 abstract description 7
- 238000010189 synthetic method Methods 0.000 abstract description 5
- 239000000047 product Substances 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 38
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910004068 NO2Cl Inorganic materials 0.000 description 2
- 229910004057 NO2F Inorganic materials 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 150000001345 alkine derivatives Chemical class 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
- 229940080818 propionamide Drugs 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001857 anti-mycotic effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 239000002543 antimycotic Substances 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- QCPORYSHAZPBCG-UHFFFAOYSA-N n-phenoxyacetamide Chemical class CC(=O)NOC1=CC=CC=C1 QCPORYSHAZPBCG-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Steroid Compounds (AREA)
Abstract
Description
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810326839.2A CN108314658B (zh) | 2018-04-12 | 2018-04-12 | 一种多取代噁唑衍生物的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810326839.2A CN108314658B (zh) | 2018-04-12 | 2018-04-12 | 一种多取代噁唑衍生物的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN108314658A true CN108314658A (zh) | 2018-07-24 |
CN108314658B CN108314658B (zh) | 2019-09-06 |
Family
ID=62897358
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201810326839.2A Active CN108314658B (zh) | 2018-04-12 | 2018-04-12 | 一种多取代噁唑衍生物的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN108314658B (zh) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108947995A (zh) * | 2018-09-17 | 2018-12-07 | 青岛科技大学 | 一种多取代噁二嗪衍生物的制备方法 |
CN109851599A (zh) * | 2019-03-19 | 2019-06-07 | 青岛科技大学 | 一种2-氨基苯并呋喃化合物的制备方法 |
CN110156710A (zh) * | 2019-04-30 | 2019-08-23 | 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) | 一种多取代噁唑类化合物的制备方法 |
CN115536605A (zh) * | 2022-08-22 | 2022-12-30 | 广东工业大学 | 一种硼试剂参与的多取代噁唑化合物的制备方法及其应用 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106749077A (zh) * | 2017-03-27 | 2017-05-31 | 广西师范大学 | 一种合成噁唑化合物的新方法 |
-
2018
- 2018-04-12 CN CN201810326839.2A patent/CN108314658B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106749077A (zh) * | 2017-03-27 | 2017-05-31 | 广西师范大学 | 一种合成噁唑化合物的新方法 |
Non-Patent Citations (3)
Title |
---|
MING LI等: "Metal-Free Direct Construction of 2-(Oxazol-5-yl)phenols from N-Phenoxyamides and Alkynylbenziodoxolones via Sequential [3,3]-Rearrangement/Cyclization", 《ORG. LETT.》 * |
QIAN WU等: "Unified synthesis of mono/bis-arylated phenols via RhIII-catalyzed dehydrogenative coupling", 《CHEM. SCI.》 * |
YING CHEN等: "A multitasking functional group leads to structural diversity using designer C–H activation reaction cascades", 《NATURE COMMUNICATIONS》 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108947995A (zh) * | 2018-09-17 | 2018-12-07 | 青岛科技大学 | 一种多取代噁二嗪衍生物的制备方法 |
CN108947995B (zh) * | 2018-09-17 | 2021-03-16 | 青岛科技大学 | 一种多取代噁二嗪衍生物的制备方法 |
CN109851599A (zh) * | 2019-03-19 | 2019-06-07 | 青岛科技大学 | 一种2-氨基苯并呋喃化合物的制备方法 |
CN109851599B (zh) * | 2019-03-19 | 2022-03-08 | 青岛科技大学 | 一种2-氨基苯并呋喃化合物的制备方法 |
CN110156710A (zh) * | 2019-04-30 | 2019-08-23 | 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) | 一种多取代噁唑类化合物的制备方法 |
CN110156710B (zh) * | 2019-04-30 | 2022-10-28 | 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) | 一种多取代噁唑类化合物的制备方法 |
CN115536605A (zh) * | 2022-08-22 | 2022-12-30 | 广东工业大学 | 一种硼试剂参与的多取代噁唑化合物的制备方法及其应用 |
CN115536605B (zh) * | 2022-08-22 | 2023-12-15 | 广东工业大学 | 一种硼试剂参与的多取代噁唑化合物的制备方法及其应用 |
Also Published As
Publication number | Publication date |
---|---|
CN108314658B (zh) | 2019-09-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN108314658B (zh) | 一种多取代噁唑衍生物的制备方法 | |
CN111925381B (zh) | 一种巴洛沙韦关键中间体的合成方法 | |
CN108794357B (zh) | 一种n-二氟甲基腙类化合物及其合成方法 | |
CN105801575A (zh) | 一种咪唑并[1,2-a]吡啶的合成方法 | |
CN115572300A (zh) | 一种磺酰胺基取代多环喹唑啉酮化合物的合成方法 | |
CN112898218B (zh) | 一锅法合成含三氟甲基噁唑酮类化合物的方法 | |
CN111574444A (zh) | 一种贝达喹啉的制备方法 | |
CN109705050B (zh) | 一种合成4-烃硫基异恶唑的方法 | |
CN111995554A (zh) | 无金属化学氧化法制备不对称有机硒醚类化合物的方法 | |
CN111943885A (zh) | 劳拉替尼中间体2-氨基-5-溴-3-羟基吡啶的合成方法 | |
CN110156710A (zh) | 一种多取代噁唑类化合物的制备方法 | |
CN112194608B (zh) | 一种可见光促进3-甲基-3-二氟乙基-2-氧化吲哚化合物的合成方法 | |
JP5665041B2 (ja) | ヨードニウム化合物、その製造方法、及び官能基化スピロ環状化合物とその製造方法 | |
CN110698426B (zh) | 叔丁醇钾高效催化制备1,3-苯并噻唑衍生物的方法 | |
CN108947995B (zh) | 一种多取代噁二嗪衍生物的制备方法 | |
CN113354498A (zh) | 一种由芳香族C-N/O/Cl/Br/I键还原为芳香族C-H/D的方法 | |
CN111892553A (zh) | 一种以醋酸铵介导的苯并噻唑类化合物的合成方法 | |
CN113004178A (zh) | 一种(e)-3-甲硫基-2-碘丙烯酸酯化合物的合成方法 | |
CN105622544B (zh) | 一种n-磺酰基-3,4-二氢-2h-1,4-噻嗪的合成方法 | |
CN104910090B (zh) | 二氢异噁唑类化合物及其合成方法 | |
CN108863830A (zh) | 一种手性芳基烯丙基胺类化合物及其合成方法 | |
CN113024475B (zh) | 一种喹喔啉酮类化合物的合成方法 | |
CN112125843B (zh) | 一种3-羟甲基-4-苯基-3,4-二氢喹啉酮化合物的制备方法 | |
CN110054597B (zh) | 一种无金属催化剂条件下合成的噻唑烷-4-酮衍生物及其制备方法 | |
JP2003206282A (ja) | オキサゾリジン−2−オン誘導体の製造法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right |
Effective date of registration: 20210617 Address after: 224500 No.50, industrial branch road, private industrial park, Tongyu Town, Binhai County, Yancheng City, Jiangsu Province Patentee after: Binhai Yuzhuo technology consulting studio Address before: No. 53, Zhengzhou Road, North District, Qingdao, Shandong Patentee before: Qingdao University Of Science And Technology |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20210630 Address after: 110027 No.1-3, No.10 Road, Shenyang Economic and Technological Development Zone, Liaoning Province Patentee after: SHENYANG SUNSHINE PHARMACEUTICAL Co.,Ltd. Address before: 224500 No.50, industrial branch road, private industrial park, Tongyu Town, Binhai County, Yancheng City, Jiangsu Province Patentee before: Binhai Yuzhuo technology consulting studio |
|
TR01 | Transfer of patent right |