MD4202C1 - Способ получения карбометокси производных спиро[циклопропан-оксиндолов] - Google Patents
Способ получения карбометокси производных спиро[циклопропан-оксиндолов] Download PDFInfo
- Publication number
- MD4202C1 MD4202C1 MDA20120031A MD20120031A MD4202C1 MD 4202 C1 MD4202 C1 MD 4202C1 MD A20120031 A MDA20120031 A MD A20120031A MD 20120031 A MD20120031 A MD 20120031A MD 4202 C1 MD4202 C1 MD 4202C1
- Authority
- MD
- Moldova
- Prior art keywords
- chh
- nmr
- mhz
- ppm
- cyclopropane
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 14
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 238000005888 cyclopropanation reaction Methods 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 238000009835 boiling Methods 0.000 claims abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 12
- 238000003786 synthesis reaction Methods 0.000 abstract description 10
- 230000036436 anti-hiv Effects 0.000 abstract description 6
- 239000003054 catalyst Substances 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 6
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 5
- 125000003003 spiro group Chemical group 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- GGFAZNCZEXSGIY-UHFFFAOYSA-N 4-diazo-1,3a-dihydroindole-2,3-dione Chemical class [N-]=[N+]=C1C=CC=C2NC(=O)C(=O)C12 GGFAZNCZEXSGIY-UHFFFAOYSA-N 0.000 abstract description 3
- -1 carbomethoxy group Chemical group 0.000 abstract description 3
- 239000002243 precursor Substances 0.000 abstract description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 60
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- 239000013078 crystal Substances 0.000 description 18
- 239000000843 powder Substances 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- HBURLQPOAYRMFA-UHFFFAOYSA-N ethyl 3-(4-bromophenyl)-1,2-oxazole-5-carboxylate Chemical compound O1C(C(=O)OCC)=CC(C=2C=CC(Br)=CC=2)=N1 HBURLQPOAYRMFA-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 102100034343 Integrase Human genes 0.000 description 1
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000005182 global health Effects 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical class C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 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
- 239000000203 mixture Substances 0.000 description 1
- 229960000689 nevirapine Drugs 0.000 description 1
- 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 description 1
- 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Abstract
Изобретение относится к синтезу спиро[циклопропан-оксиндолов], функционализированных карбометокси группой, которые могут служить прекурсорами в синтезе веществ с анти-ВИЧ активностью.Способ включает реакцию циклопропанирования диазоизатинов метилакрилатом, который используют как в качестве реагента, так и растворителя при температуре его кипения.Предложенный способ позволяет более быстрое проведение реакции с высокими выходами, без использования катализаторов и инертной атмосферы.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20120031A MD4202C1 (ru) | 2012-03-21 | 2012-03-21 | Способ получения карбометокси производных спиро[циклопропан-оксиндолов] |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20120031A MD4202C1 (ru) | 2012-03-21 | 2012-03-21 | Способ получения карбометокси производных спиро[циклопропан-оксиндолов] |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MD4202B1 MD4202B1 (en) | 2013-02-28 |
| MD4202C1 true MD4202C1 (ru) | 2013-09-30 |
Family
ID=47831223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20120031A MD4202C1 (ru) | 2012-03-21 | 2012-03-21 | Способ получения карбометокси производных спиро[циклопропан-оксиндолов] |
Country Status (1)
| Country | Link |
|---|---|
| MD (1) | MD4202C1 (ru) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57102863A (en) * | 1980-12-16 | 1982-06-26 | Takeda Chem Ind Ltd | Spiroindolinone and its preparation |
| US6046341A (en) * | 1995-10-24 | 2000-04-04 | Sanofi-Synthelabo | 3-spiro-indolin-2-one derivatives |
| WO2004037247A1 (en) * | 2002-10-21 | 2004-05-06 | Irm Llc | Oxindoles with anti-hiv activity |
| US20050015776A1 (en) * | 2003-06-02 | 2005-01-20 | Bimal Mehta | Processing convoy workflow scenarios |
| WO2007008664A1 (en) * | 2005-07-13 | 2007-01-18 | Allergan, Inc. | 3-spir0cycl0pr0pyl2-0xind0le kinase inhibitors |
-
2012
- 2012-03-21 MD MDA20120031A patent/MD4202C1/ru not_active IP Right Cessation
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57102863A (en) * | 1980-12-16 | 1982-06-26 | Takeda Chem Ind Ltd | Spiroindolinone and its preparation |
| US6046341A (en) * | 1995-10-24 | 2000-04-04 | Sanofi-Synthelabo | 3-spiro-indolin-2-one derivatives |
| WO2004037247A1 (en) * | 2002-10-21 | 2004-05-06 | Irm Llc | Oxindoles with anti-hiv activity |
| US20050015776A1 (en) * | 2003-06-02 | 2005-01-20 | Bimal Mehta | Processing convoy workflow scenarios |
| WO2007008664A1 (en) * | 2005-07-13 | 2007-01-18 | Allergan, Inc. | 3-spir0cycl0pr0pyl2-0xind0le kinase inhibitors |
Non-Patent Citations (6)
| Title |
|---|
| Cava M.P., Litle R.L., Napier D.R. J. Amer. Chem. Soc., 1958, 80, 2257-2262 * |
| Chen S., Ma J., Wang J. Tetrahedron Lett., 2008, 49, 6781-6783 * |
| Jiang T., Kuhen K. L., Wolff K., Yin H., Bieza K., Caldwell J., Bursulaya B., Tuntland T., Zhang K., Karanewsky D., He Y. Bioorganic & Medicinal Chemistry Letters, 2006, 16, 2109-2112 * |
| Jiang T., Kuhen K. L., Wolff K., Yin H., Bieza K., Caldwell J., Bursulaya B., Wu T. Y. H., He Y. Bioorganic & Medicinal Chemistry Letters, 2006, 16, 2105-2108 * |
| Kumari G., Nutan I., Modi M., Gupta S. K., Singh R. K. Eur. J. Med. Chem., 2011, 46, 1181-1188 * |
| Marti C., Carreira E.M. J. Am. Chem. Soc., 2005, 127, 11505-11515 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MD4202B1 (en) | 2013-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6266509B2 (ja) | Ｚ選択的閉環メタセシス反応 | |
| Alcaide et al. | Gold catalyzed oxycyclizations of alkynols and alkyndiols | |
| Inack‐Ngi et al. | Copper‐catalyzed preparation of γ‐alkylidenebutenolides and isocoumarins under mild palladium‐free conditions | |
| Poudel et al. | An advanced and novel one-pot synthetic method for diverse benzo [c] chromen-6-ones by transition-metal free mild base-promoted domino reactions of substituted 2-hydroxychalcones with β-ketoesters and its application to polysubstituted terphenyls | |
| Schindler et al. | Rapid formation of complexity in the total synthesis of natural products enabled by oxabicyclo [2.2. 1] heptene building blocks | |
| Yoshida et al. | Highly diastereoselective synthesis of tetrahydrobenzofuran derivatives by palladium-catalyzed reaction of propargylic esters with substituted β-dicarbonyl compounds | |
| US10844033B2 (en) | Method for preparing delta-lactones | |
| Liu et al. | Regioselective Synthesis of Aurone Derivatives via PBu3‐Catalyzed Cyclization of 2‐Alkynoylphenols | |
| Mandal et al. | L-Proline-catalysed synthesis of chromeno [2, 3-b] chromene from 4-hydroxy-2 H-chromene-2-thione and an anti-proliferative study | |
| Alizadeh et al. | Synthesis of 5, 6-dihydroquinolines and succinates via the reaction of α, α-dicyanoolefins and acetylenic esters in a ratio of 2: 1 | |
| Song et al. | The use of iminopyridines as efficient ligands in the palladium (II)-catalyzed cyclization of (Z)-4′-acetoxy-2′-butenyl 2-alkynoates | |
| JP2021516657A (ja) | 四座ｐｎｎｐ配位子ルテニウム錯体でのカルボニルの水素化 | |
| Redon et al. | A new oxa-Michael reaction and a gold-catalysed cyclisation en route to C-glycosides | |
| MD4202C1 (ru) | Способ получения карбометокси производных спиро[циклопропан-оксиндолов] | |
| Tiefenbacher et al. | An expeditious asymmetric formal synthesis of the antibiotic platensimycin | |
| Praveen et al. | Synergistic iron-and-amine catalysis in carbocyclizations | |
| Khodabakhshi et al. | Sodium Tungstate: The First Application as Non‐oxidative Catalyst in Organic Synthesis | |
| CN111004198B (zh) | 一种苯并吡喃衍生物的合成方法 | |
| MD4201C1 (ru) | Способ получения карбонитрилпроизводных спиро[циклопропан-оксиндолов] | |
| Mirzaei et al. | Palladium-Catalyzed Carbonylation of Coumarin C (sp2)–H Bonds: A New Entry to Arylcoumarin Ketones | |
| Wittmann et al. | Auto tandem triple cascade organocatalysis: access to bis-lactone and butenolide derivatives | |
| Tanabe et al. | Studies on ring-closing metathesis for the formation of the 11-membered ring system of daphnezomine C | |
| CN106946641A (zh) | 一种制备反式二苯基乙烯类化合物的方法 | |
| Tsai et al. | A New Synthesis of Angelicin from 7‐Hydroxycoumarin via C‐Propenation‐O‐Vinylation and Ring‐Closing Metathesis | |
| WO2007105233A2 (en) | An improved process for the preparation of 4,5,6-substituted 3,4-dihydropyrimidin-2-ones and their 2-thioxo analogues |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG4A | Patent for invention issued | ||
| KA4A | Patent for invention lapsed due to non-payment of fees (with right of restoration) | ||
| MM4A | Patent for invention definitely lapsed due to non-payment of fees |