MD4233C1 - Catalyst for the synthesis of 2-pyrrol-3-iloxindole derivatives - Google Patents
Catalyst for the synthesis of 2-pyrrol-3-iloxindole derivatives Download PDFInfo
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- MD4233C1 MD4233C1 MDA20120024A MD20120024A MD4233C1 MD 4233 C1 MD4233 C1 MD 4233C1 MD A20120024 A MDA20120024 A MD A20120024A MD 20120024 A MD20120024 A MD 20120024A MD 4233 C1 MD4233 C1 MD 4233C1
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- pyrrole
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- 239000003054 catalyst Substances 0.000 title claims abstract description 22
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 13
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 11
- 239000002608 ionic liquid Substances 0.000 claims abstract description 12
- -1 tetrafluoroborate Chemical compound 0.000 claims description 6
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- PSCMQHVBLHHWTO-UHFFFAOYSA-K indium(iii) chloride Chemical compound Cl[In](Cl)Cl PSCMQHVBLHHWTO-UHFFFAOYSA-K 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000010413 mother solution Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000005712 Baylis-Hillman reaction Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- GNHMRTZZNHZDDM-UHFFFAOYSA-N 3-chloropropionitrile Chemical compound ClCCC#N GNHMRTZZNHZDDM-UHFFFAOYSA-N 0.000 description 1
- HYHFPMWIIOXTBM-UHFFFAOYSA-N 3-phenacylidene-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2C1=CC(=O)C1=CC=CC=C1 HYHFPMWIIOXTBM-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 238000006086 Paal-Knorr synthesis reaction Methods 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- JHXKRIRFYBPWGE-UHFFFAOYSA-K bismuth chloride Chemical compound Cl[Bi](Cl)Cl JHXKRIRFYBPWGE-UHFFFAOYSA-K 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Invenţia se referă la chimia organică, şi anume la un catalizator pentru sinteza derivaţilor 2-pirol-3-iloxindolului.Conform invenţiei, se revendică aplicarea lichidului ionic tetrafluoroborat de 1,3-di(2-cianoetil)-1H-imidazol-3-iu cu formula:în calitate de catalizator pentru sinteza derivaţilor 2-pirol-3-iloxindolului.The invention relates to organic chemistry, namely to a catalyst for the synthesis of 2-pyrrole-3-yloxindole derivatives. According to the invention, the application of 1,3-di (2-cyanoethyl) -1H-imidazole-3- tetrafluoroborate ionic liquid is claimed. and with the formula: as catalyst for the synthesis of 2-pyrrole-3-yloxindole derivatives.
Description
Invenţia se referă la chimia organică, şi anume la un catalizator pentru sinteza derivaţilor 2-pirol-3-iloxindolului. The invention relates to organic chemistry, namely to a catalyst for the synthesis of 2-pyrrole-3-yloxindole derivatives.
În prezent, lichidele ionice sunt tot mai frecvent aplicate în sinteza organică în calitate de catalizatori la obţinerea substanţelor cu activitate importantă. Currently, ionic liquids are more and more frequently applied in organic synthesis as catalysts to obtain substances with important activity.
La sinteza derivaţilor 2-pirol-3-iloxindolului în calitate de catalizatori se utilizează un număr mare de compuşi: acizi Lewis, InCl3, SnCl2·H2O, BiCl3. Catalizatorii menţionaţi fac parte din grupul reagenţilor toxici, iar reziduurile rămase după finisarea reacţiei poluează mediul înconjurător. A large number of compounds are used as catalysts for the synthesis of 2-pyrrole-3-yloxindole derivatives: Lewis acids, InCl3, SnCl2·H2O, BiCl3. The mentioned catalysts are part of the group of toxic reagents, and the residues left after finishing the reaction pollute the environment.
Actualmente, conform cerinţelor faţă de reagenţii folosiţi în diferite reacţii chimice, accentul se pune pe înlocuirea catalizatorilor toxici, corozivi şi explozibili cu cei de alternativă, mai puţin nocivi şi ecologic puri. Currently, according to the requirements for reagents used in various chemical reactions, the focus is on replacing toxic, corrosive and explosive catalysts with alternative, less harmful and ecologically pure ones.
Este cunoscută compoziţia catalitică pentru reacţia Morita-Baylis-Hillman, ce conţine 4-dimetilaminopiridină şi hexafluorfosfat de 1,3-di(2-cianoetil)imidazoliu în calitate de lichid ionic, într-un raport al componentelor, respectiv, de 8:1 [1]. The catalytic composition for the Morita-Baylis-Hillman reaction is known, containing 4-dimethylaminopyridine and 1,3-di(2-cyanoethyl)imidazolium hexafluorophosphate as an ionic liquid, in a ratio of the components, respectively, of 8:1 [1].
Dezavantajul acestei compoziţii constă în faptul că aceasta poate fi utilizată doar pentru un număr limitat de substraturi organice, iar reacţiile se caracterizează printr-un randament moderat. The disadvantage of this composition is that it can only be used for a limited number of organic substrates, and the reactions are characterized by a moderate yield.
În calitate de cea mai apropiată soluţie serveşte obţinerea 2-pirol-3-iloxindolilor, unde în calitate de catalizator se utilizează InCl3. Astfel de substanţe au fost sintetizate într-o singură etapă la interacţiunea a trei reagenţi: 3-fenil-acetilidenoxindolilor, β-cetoesterilor şi acetatului de amoniu la refluxare în alcool, în care are loc adiţia de tipul Michael, condensarea Paal-Knorr cu formarea derivaţilor 2-pirol-3-iloxindolilor. Catalizatorul InCl3 se foloseşte în reacţie o singură dată, nu se utilizează din mediul reacţiei [2]. The closest solution is the preparation of 2-pyrrole-3-yloxindoles, where InCl3 is used as a catalyst. Such substances were synthesized in a single step by the interaction of three reagents: 3-phenyl-acetylideneoxindoles, β-ketoesters and refluxing ammonium acetate in alcohol, in which Michael addition, Paal-Knorr condensation with the formation 2-pyrrole-3-yloxindol derivatives. The InCl3 catalyst is used in the reaction only once, it is not used from the reaction medium [2].
Dezavantajul acestui procedeu constă în faptul că după eliminarea 2-pirol-3-iloxindolului (IV) din reacţie amestecul reactant se elimină şi nu sunt utilizate catalizatorul şi soluţia-mamă folosite în reacţie. The disadvantage of this process is that after the elimination of 2-pyrrole-3-yloxindole (IV) from the reaction, the reactant mixture is eliminated and the catalyst and mother solution used in the reaction are not used.
Dezavantajele catalizatorului utilizat în reacţia de sinteză a derivaţilor 2-pirol-3-iloxindolului constau în aceea că catalizatorul este: The disadvantages of the catalyst used in the synthesis reaction of 2-pyrrole-3-yloxindole derivatives are that the catalyst is:
- toxic; - toxic;
- costisitor; - expensive;
- se foloseşte în reacţie o singură dată; - it is used in the reaction only once;
- se cere o cantitate de catalizator sporită. - an increased amount of catalyst is required.
Problema tehnică pe care o rezolvă invenţia constă în aceea că se propune în calitate de catalizator eficient la sinteza derivaţilor 2-pirol-3-iloxindolului lichidul ionic tetrafluoroborat de 1,3-di(2-cianoetil)-1H-imidazol-3-iu - un compus accesibil, cu activitate catalitică înaltă, care poate fi utilizat multiplu. The technical problem that the invention solves is that the tetrafluoroborate ionic liquid of 1,3-di(2-cyanoethyl)-1H-imidazol-3-iu is proposed as an effective catalyst for the synthesis of 2-pyrrole-3-yloxindole derivatives - an affordable compound with high catalytic activity that can be used multiple times.
Problema se rezolvă prin aceea că se propune aplicarea lichidului ionic tetrafluoroborat de 1,3-di(2-cianoetil)-1H-imidazol-3-iu cu formula: The problem is solved by proposing the application of 1,3-di(2-cyanoethyl)-1H-imidazol-3-iu tetrafluoroborate ionic liquid with the formula:
(I) (I)
în calitate de catalizator pentru sinteza derivaţilor 2-pirol-3-iloxindolului. as a catalyst for the synthesis of 2-pyrrole-3-yloxindole derivatives.
Catalizatorul propus - tetrafluoroborat de 1,3-di(2-cianoetil)-1H-imidazol-3-iu (I), conform invenţiei, prezintă un lichid ionic, care se obţine prin reacţia de cuaternizare a 1-(2-cianoetil)imidazolului cu 3-cloropropionitril într-un raport echimolar la refluxare în mediu de acetonă, urmată de substituţia anionului de clor Cl- cu anionul BF4 -. The proposed catalyst - 1,3-di(2-cyanoethyl)-1H-imidazol-3-io tetrafluoroborate (I), according to the invention, presents an ionic liquid, which is obtained by the quaternization reaction of 1-(2-cyanoethyl) of imidazole with 3-chloropropionitrile in an equimolar ratio at reflux in acetone medium, followed by the substitution of Cl- chlorine anion with BF4 - anion.
Lichidul ionic (I) se obţine cu un randament de 98%. Prezintă o substanţă solidă, higroscopică. P.t. - 70…74°C (recristalizat din C2H5OH absolut), cristale albe-gălbui. Spectrul IR (ν, cm-1, peliculă): 1037 (BF4 -), 1453, 1576, 3169 (CH=CH), 2258 (CN), 756, 2988 (CH2). Spectrul 1H RMN (80 MHz, CCl4:DMSO-d6 4:1, δ, ppm, J/Hz): 3,14 (t, 4H, 5CH2, 8CH2, J=6,4), 4,50 (t, 4H, 4CH2, 7CH2, J=6,4), 7,62, 7,74, 9,08 (3s, 3H, imidazol). Spectrul 13C (20 MHz, CCl4: DMSO-d6 4:1, δ, ppm): 139,98 (1C), 13,16 (3C), 122,00 (2C), 116,04 (9C), 115,90 (6C), 47,92 (4C), 41,19 (7C), 17,14 (5C), 11,12 (8C). Găsit, (%): C 41,38; H 4,63; N 20,68. C9H11BF4N4. Calculat, (%): C 41,26; H 4,23; N 21,38. The ionic liquid (I) is obtained with a yield of 98%. It presents a solid, hygroscopic substance. p.t. - 70...74°C (recrystallized from absolute C2H5OH), yellowish-white crystals. IR spectrum (ν, cm-1, film): 1037 (BF4 -), 1453, 1576, 3169 (CH=CH), 2258 (CN), 756, 2988 (CH2). 1H NMR spectrum (80 MHz, CCl4:DMSO-d6 4:1, δ, ppm, J/Hz): 3.14 (t, 4H, 5CH2, 8CH2, J=6.4), 4.50 (t, 4H, 4CH2, 7CH2, J=6.4), 7.62, 7.74, 9.08 (3s, 3H, imidazole). 13C spectrum (20 MHz, CCl4: DMSO-d6 4:1, δ, ppm): 139.98 (1C), 13.16 (3C), 122.00 (2C), 116.04 (9C), 115, 90 (6C), 47.92 (4C), 41.19 (7C), 17.14 (5C), 11.12 (8C). Found, (%): C 41.38; H 4.63; N 20.68. C9H11BF4N4. Calculated, (%): C 41.26; H 4.23; N 21,38.
Lichidul ionic tetrafluoroborat de 1,3-di(2-cianoetil)-1H-imidazol-3-iu este utilizat în calitate de catalizator în reacţia Morita-Baylis-Hillman (Şargorovschi V., Sucman N., Iudin T., Duca D., Stângaci E., Prodius D., Pogrebnoi S., Macaev F. Ionic liquids derivative of 1H-imidazole as novel reagents, catalysts and solvents. Chemistry Journal of Moldova, 2010, vol. 5, p. 36-56). The 1,3-di(2-cyanoethyl)-1H-imidazol-3-io tetrafluoroborate ionic liquid is used as a catalyst in the Morita-Baylis-Hillman reaction (Şargorovschi V., Sucman N., Iudin T., Duca D ., Stângaci E., Prodius D., Pogrebnoi S., Macaev F. Ionic liquids derivative of 1H-imidazole as novel reagents, catalysts and solvents. Chemistry Journal of Moldova, 2010, vol. 5, p. 36-56).
Avantajul invenţiei constă în faptul că catalizatorul (I) poate fi utilizat în condiţiile reacţiei de sinteză a 2-pirol-3-iloxindolului (IV) de mai multe ori şi randamentul reacţiei rămâne sporit. Capacitatea catalitică se păstrează şi soluţia-mamă, la care se adaugă numai reagenţii iniţiali, poate fi folosită de repetate ori. The advantage of the invention lies in the fact that the catalyst (I) can be used in the conditions of the synthesis reaction of 2-pyrrole-3-yloxindole (IV) several times and the yield of the reaction remains increased. The catalytic capacity is preserved and the mother solution, to which only the initial reagents are added, can be used repeatedly.
Procesul chimic poate fi repetat până la cinci ori, şi randamentul reacţiei este satisfăcător în intervalul de la 98 până la 63%. Reacţia are loc conform schemei: The chemical process can be repeated up to five times, and the reaction yield is satisfactory in the range of 98 to 63%. The reaction takes place according to the scheme:
(II) (III) (IV) (II) (III) (IV)
Exemplu de realizare a invenţiei Example of realization of the invention
1. La amestecul format din 0,01 mol (2,49 g) 3-fenacilidenoxindol (II), 0,01 mol (1,3 g, 1,27 ml) ester acetilacetic (III) şi 0,025 mol (1,93 g) acetat de amoniu în 40…45 ml de alcool etilic se adaugă lichidul ionic (I) 6 mmol (0,015 g, 6%). Masa reactantă eterogenă, de culoare roşie se supune la refluxare. Peste 3…5 min ea devine omogenă, se decolorează şi se formează un precipitat alb. Refluxarea durează timp de 20 min. Apoi masa reactantă se răceşte până la temperatura camerei, precipitatul se filtrează şi se spală pe filtru cu o cantitate minimală de etanol. Compusul obţinut se usucă şi se determină indicii fizico-chimici. 1. To the mixture consisting of 0.01 mol (2.49 g) 3-phenacylideneoxindole (II), 0.01 mol (1.3 g, 1.27 ml) acetylacetic ester (III) and 0.025 mol (1.93 g) ammonium acetate in 40...45 ml of ethyl alcohol, add the ionic liquid (I) 6 mmol (0.015 g, 6%). The heterogeneous, red-colored reactant mass undergoes reflux. After 3...5 min it becomes homogeneous, discolors and a white precipitate forms. The reflux lasts for 20 min. Then the reactant mass is cooled to room temperature, the precipitate is filtered and washed on the filter with a minimal amount of ethanol. The obtained compound is dried and physico-chemical indices are determined.
S-a obţinut o substanţă cristalină de culoare alb-galbuie: 3,53 g (98%) (IV). P.t. 317…318°C (recristalizat din C2H5OH). Spectrul IR (ν, cm-1, peliculă): 3356, 3210, 1700, 1668, 1445, 1090, 700. Spectrul 1H RMN (400 MHz, DMSO-d6, δ, ppm, J/Hz): 0,84 (t, 3H, J=6,9 Hz), 2,48 (s, 3H), 3,64 (m, 2H), 4,56 (s, 1H), 6,76 (m, 3H), 6,70 (m, 1H), 7,12 (m, 5H), 10,35 (s, 1H, NH), 11,60 (s, 1H; NH). Găsit, (%): C 73,28; H 5,54; N 7,90. C22H20N2O3. Calculat, (%): C 73,32; H 5,59; N 7,77. A yellowish-white crystalline substance was obtained: 3.53 g (98%) (IV). p.t. 317…318°C (recrystallized from C2H5OH). IR spectrum (ν, cm-1, film): 3356, 3210, 1700, 1668, 1445, 1090, 700. 1H NMR spectrum (400 MHz, DMSO-d6, δ, ppm, J/Hz): 0.84 ( t, 3H, J=6.9 Hz), 2.48 (s, 3H), 3.64 (m, 2H), 4.56 (s, 1H), 6.76 (m, 3H), 6, 70 (m, 1H), 7.12 (m, 5H), 10.35 (s, 1H, NH), 11.60 (s, 1H; NH). Found, (%): C 73.28; H 5.54; No. 7.90. C22H20N2O3. Calculated, (%): C 73.32; H 5.59; N 7.77.
2. Soluţia-mamă din experimentul 1, după filtrarea precipitatului (IV) a fost folosită ca mediu reactant în care s-au adăugat reagenţii iniţiali (II, III şi acetatul de amoniu). 2. The mother solution from experiment 1, after filtering the precipitate (IV) was used as a reactant medium in which the initial reagents (II, III and ammonium acetate) were added.
Procedeul se repetă de câteva ori, însă timpul reacţiei se prelungeşte până la o oră (vezi tabelul). The procedure is repeated several times, but the reaction time is extended up to one hour (see the table).
Tabel Table
Variaţia randamentului şi timpului de reacţie la folosirea repetată a catalizatorului The variation of yield and reaction time upon repeated use of the catalyst
Nr. reacţiei Formula compusului Timpul, min Randamentul, % 1 20 98 2 25 97,22 3 35 90,5 4 45 88,4 5 60 63 No. of the reaction Formula of the compound Time, min Yield, % 1 20 98 2 25 97.22 3 35 90.5 4 45 88.4 5 60 63
Rezultatul invenţiei constă în faptul că lichidul ionic - tetrafluoroborat de 1,3-di(2-cianoetil)-1H-imidazol-3-iu (I) în cantitate de 6 mmol catalizează eficient sinteza substanţelor heterociclice (IV) şi poate fi folosit repetat în reacţie pentru sinteza acestor substanţe cu un randament satisfăcător. The result of the invention consists in the fact that the ionic liquid - tetrafluoroborate of 1,3-di(2-cyanoethyl)-1H-imidazol-3-io (I) in an amount of 6 mmol effectively catalyzes the synthesis of heterocyclic substances (IV) and can be used repeatedly in the reaction for the synthesis of these substances with a satisfactory yield.
1. MD 4062 B1 2010.08.31 1. MD 4062 B1 2010.08.31
2. Gnanamani Shanthi, Paramasivan T. Perumal. InCl3-catalyzed efficient one-pot synthesis of 2-pyrrolo-3-yloxindoles. Tetrahedron Letters, 2009, 50, p. 3959-3962 2. Gnanamani Shanthi, Paramasivan T. Perumal. InCl3-catalyzed efficient one-pot synthesis of 2-pyrrolo-3-yloxindoles. Tetrahedron Letters, 2009, 50, pp. 3959-3962
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| WO2007112238A2 (en) * | 2006-03-24 | 2007-10-04 | Chevron U.S.A. Inc. | Alkylation process using an alkyl halide promoted ionic liquid catalyst |
| CN101508669A (en) * | 2009-03-26 | 2009-08-19 | 浙江工业大学 | Green synthesis of indole compounds |
| CN101791574A (en) * | 2010-03-24 | 2010-08-04 | 淮北煤炭师范学院 | Catalyst loaded with chiral imidazolium and preparation method thereof |
| MD4062B1 (en) * | 2010-01-16 | 2010-08-31 | Institutul De Chimie Al Academiei De Stiinte A Moldovei | Catalytic composition for the Morita-Baylis-Hillman reaction |
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Patent Citations (7)
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|---|---|---|---|---|
| US20030050512A1 (en) * | 2001-06-26 | 2003-03-13 | Mehnert Christian Peter | Process for conducting aldol condensation reactions in ionic liquid media |
| US20050101786A1 (en) * | 2002-07-18 | 2005-05-12 | Steven Dell | N-alkylation of indole derivatives |
| WO2005019185A1 (en) * | 2003-08-26 | 2005-03-03 | Ecole Polytechnique Federale De Lausanne (Epfl) | Ionic liquids based on imidazolium salts incorporating a nitrile functionality |
| WO2007112238A2 (en) * | 2006-03-24 | 2007-10-04 | Chevron U.S.A. Inc. | Alkylation process using an alkyl halide promoted ionic liquid catalyst |
| CN101508669A (en) * | 2009-03-26 | 2009-08-19 | 浙江工业大学 | Green synthesis of indole compounds |
| MD4062B1 (en) * | 2010-01-16 | 2010-08-31 | Institutul De Chimie Al Academiei De Stiinte A Moldovei | Catalytic composition for the Morita-Baylis-Hillman reaction |
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Non-Patent Citations (1)
| Title |
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| Gnanamani Shanthi, Paramasivan T. Perumal. InCl3-catalyzed efficient one-pot synthesis of 2-pyrrolo-3-yloxindoles. Tetrahedron Letters, 2009, 50, p. 3959-3962 * |
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