CS264999B1 - 3-triphenylphosphonium oxindolate and process for preparing thereof - Google Patents
3-triphenylphosphonium oxindolate and process for preparing thereof Download PDFInfo
- Publication number
- CS264999B1 CS264999B1 CS883371A CS337188A CS264999B1 CS 264999 B1 CS264999 B1 CS 264999B1 CS 883371 A CS883371 A CS 883371A CS 337188 A CS337188 A CS 337188A CS 264999 B1 CS264999 B1 CS 264999B1
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- CS
- Czechoslovakia
- Prior art keywords
- triphenylphosphonium
- oxindolate
- compound
- formula
- preparing
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims abstract description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims abstract description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 3
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims abstract description 3
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 claims abstract 2
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- ULRFUWBJAWYGIS-UHFFFAOYSA-M (2-isocyanatophenyl)methyl-triphenylphosphanium bromide Chemical compound [Br-].N(=C=O)C1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC=C1 ULRFUWBJAWYGIS-UHFFFAOYSA-M 0.000 abstract description 2
- 239000013543 active substance Substances 0.000 abstract description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- -1 alkylidene oxindoles Chemical class 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
Abstract
Riešenie sa týká nového 3-trifenylfosfónium oxindolátu. Zlúčenina sa připravuje tak, že sa na 2-izokyanátobenzyltrifenylfosfónium bromid pdsobi látkami vybratými zo skupiny zahrnujúci trietylamín, alkalické hydroxidy, hydrogenuhličitany v prostředí organických rozpúšťadiel alebo vody, resp. v ich zmesiach v rozmedzí teplót 0 až 100 °C. Novů zlúčeninu možno využit pri syntéze biologicky účinných látok indolového typu.The solution relates to the novel 3-triphenylphosphonium oxindole. The compound is prepared by contacting 2-isocyanatobenzyltriphenylphosphonium bromide acts as substances selected from the group consisting of triethylamine, alkali hydroxides, bicarbonates in an organic solvent environment or water, respectively. in their mixtures within the range temperature 0 to 100 ° C. Novy compound can be utilized in biological synthesis active substances of the indole type.
Description
Vynález sa týká 3-trifenylfosfónium oxidolátu vzorca IThe invention relates to 3-triphenylphosphonium oxidolate of formula I
H VOH V O
Ό wΌ w
/P'C6H5>3 (I) a spósobu jeho přípravy.( P ) C 6 H 5> 3 (I) and a process for its preparation.
Heterocyklické ylidy fosforu majú dóležité miesto v syntéze biologicky účinných látok, (J. J. Pappas, E. Gancher: Heterocycl. Chem. 6, 265 (1969).Heterocyclic phosphorus ylides have an important place in the synthesis of biologically active substances, (J. J. Pappas, E. Gancher: Heterocycl. Chem. 6, 265 (1969)).
Št.údiom. literatúry sa ukázalo, že 3-triefenylfosfónium oxindolát je novou, v literatúre doteraz neopísanou zlúčeninou.Št.údiom. It has been shown in the literature that 3-triphenylphosphonium oxindolate is a novel compound not previously reported in the literature.
Podstata spósobu přípravy 3-trifenylfosfónium oxindolátu podlá vynálezu spočívá v tom, že sa na 2-izokyanátobenzyltrifenylfosfónium bromid vzorca II (+) ,ch2-p(c6h5)3 The process according to the invention for the preparation of 3-triphenylphosphonium oxindolate consists in the formation of 2-isocyanate-benzyltriphenylphosphonium bromide of the formula II (+), ch 2 -p (c 6 h 5 ) 3
(II) pósobí látkou vybratou zo skupiny zahrnujúci trietylamín, alkalické hydroxidy, hydrogenuhličitany a uhličitany v prostředí organických rozpúšťadiel alebo vody, resp. v ich zmesiach v rozmedzí teplót 0 až 100 °C.(II) acts with a substance selected from the group consisting of triethylamine, alkali hydroxides, bicarbonates and carbonates in an organic solvent or water environment, respectively; in mixtures thereof at temperatures ranging from 0 to 100 ° C.
3-trifenylfosfónium oxindolát podlá vynálezu představuje nový a reaktívny typ heterocyklického ylidu schopného vstupovať s rozmanitými karbonylovými zlúčeninami do Wittigovej reakcie za vzniku alkylidénoxindolov, ktoré sú využitelné pre syntézu biologicky účinných látok indolového typu.The 3-triphenylphosphonium oxindolate of the present invention is a novel and reactive type of heterocyclic ylide capable of entering with the various carbonyl compounds into the Wittig reaction to give alkylidene oxindoles useful for the synthesis of biologically active indole-type compounds.
Predmet vynálezu ilustrujú ale neobmedzujú následovně příklady:The invention is illustrated but not limited by the following examples:
Příklad 1Example 1
Ku 47,4 g (0,1 mol) 2-izokyanátotrifenylfosfónium bromidu sa přidalo 10,1 g (0,1 mol) trietylamínu. Zmes sa miešala 1 h. Vylúčený 3-trifenylfosfónium oxindolát bol odfiltrovaný a krystalizovaný z acetonitrilu. Výťažok 72 i. T. t. 218 až 232 °C.To 47.4 g (0.1 mol) of 2-isocyanate-triphenylphosphonium bromide was added 10.1 g (0.1 mol) of triethylamine. The mixture was stirred for 1 h. The precipitated 3-triphenylphosphonium oxindolate was filtered off and crystallized from acetonitrile. Yield 72 i. T. t. Mp 218-232 ° C.
Príklad2Example 2
Roztok 47,4 g (0,1 mol) 2-izokyanátotrifenylfosfónium bromidu v 200 ml acetčnu sa v priebenu 10 min přidal k 10,6 g (0,1 mol) uhličitanu sodného v 100 ml vody za miešania. Vylúčený produkt bol odfiltrovaný a spracovaný ako v příklade 1. Výťažok 48 %.A solution of 47.4 g (0.1 mol) of 2-isocyanate-triphenylphosphonium bromide in 200 ml of acetic acid was added over 10 min to 10.6 g (0.1 mol) of sodium carbonate in 100 ml of water with stirring. The precipitated product was filtered off and worked up as in Example 1. Yield 48%.
Příklad 3Example 3
47,4 g (0,1 mol) pevného 2-izokyanátobenzyltrifenylfosfónium bromidu sa postupné přidává k roztoku 8,4 g (0,1 mol) hydrogenuhličitanu sodného v 150 ml vody pri teplote 50 °C za miešania. Po přidaní celého množstva sa zmes mieša 1 h, vylúčený produkt sa odfiltruje a spracuje ako v příklade 1. Výťažok 55 %.47.4 g (0.1 mol) of solid 2-isocyanatobenzyltriphenylphosphonium bromide are gradually added to a solution of 8.4 g (0.1 mol) of sodium bicarbonate in 150 ml of water at 50 ° C with stirring. After the addition was complete, the mixture was stirred for 1 h, the precipitated product was filtered off and worked up as in Example 1. Yield 55%.
Získaný 3-trifenylfosfónium oxindolát (I) je žitá kryštalická zlúčenina, t. t. 218 až 232 °C (za rozkladu).The obtained 3-triphenylphosphonium oxindolate (I) is a rye crystalline compound, m.p. t. Mp 218-232 ° C (dec.).
Sumárny vzorec: C26H20NOP Molekulová hmotnost: 393,2Summary formula: C 26 H 20 NOP Molecular Weight: 393,2
IČ spektrum: cm (CHCl^) ; 1 653 (C=O) .IR: cm (CHCl3); 1653 (C = O).
1H NMR spektrum: (Γ, ppm (CDC13: dg-DMSO = 3:1); 6,40 dd 1 H NMR Spectrum: (Γ, ppm (CDC1 3: dg-DMSO = 3: 1), 6.40 dd
1H(H-5) 6,53 d 1H(H-7), 6,60 dd lH(H-4, J(PH) = 1,9 Hz), 7,01 dd 1H H-6, J(PH) = 2 Hz),1H (H-5) 6.53 d 1H (H-7), 6.60 dd 1H (H-4, J (PH) = 1.9 Hz), 7.01 dd 1H H-6, J (PH) ) = 2 Hz)
7,55 až 7,85 m 15H (P(C,Hc),).7.55 to 7.85 m 15 H (P (C, Hc),).
o 5 3o 5 3
Spektrálné meraniaSpectral measurements
IČ spektrá namerali sa na spektrofotometr! Specord IR 75 (Carl Zeiss Jena). NMR spektrá boli namerané na 100 MHz spektrometr! Tesla BS 567 (25,12 MHz, FT) .IR spectra were recorded on a spectrophotometer! Specord IR 75 by Carl Zeiss Jena. NMR spectra were recorded on a 100 MHz spectrometer. Tesla BS 567 (25.12 MHz, FT).
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS883371A CS264999B1 (en) | 1988-05-19 | 1988-05-19 | 3-triphenylphosphonium oxindolate and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS883371A CS264999B1 (en) | 1988-05-19 | 1988-05-19 | 3-triphenylphosphonium oxindolate and process for preparing thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS337188A1 CS337188A1 (en) | 1988-12-15 |
| CS264999B1 true CS264999B1 (en) | 1989-09-12 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS883371A CS264999B1 (en) | 1988-05-19 | 1988-05-19 | 3-triphenylphosphonium oxindolate and process for preparing thereof |
Country Status (1)
| Country | Link |
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| CS (1) | CS264999B1 (en) |
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1988
- 1988-05-19 CS CS883371A patent/CS264999B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS337188A1 (en) | 1988-12-15 |
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