- Synthesis of 5,6-carbonyldioxyindole, a melanogenic cyclic carbonate ester of 5,6-dihydroxyindole
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5,6-Carbonyldioxyindole (4), a melanogenic derivative of 5,6-dihydroxyindole (1), was synthesized by a procedure starting with 3,4-methylenedioxycinnamic acid. Compound 4 is a stable crystalline solid which is readily hydrolyzed to 1, a key intermediate on the biosynthetic pathway from tyrosine to melanin.
- Lutz,McNamara,Olinger,et al.
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- INDOLE COMPOUND, OXIDATION DYE INTERMEDIATE, METHOD FOR PRODUCING INDOLE COMPOUND, AND METHOD FOR PRODUCING OXIDATION DYE-CONTAINING SOLUTION
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PROBLEM TO BE SOLVED: To provide a novel indole compound to be a precursor of 5,6-dihydroxy indole, which has the nature of being easily oxidized and is, therefore, limited in its methods for production, a method for producing the indole compound, and a method for producing an oxidation dye-containing solution from the indole compound. SOLUTION: According to a method, a compound of formula (III) and boron trihalide are reacted to synthesize an indole compound, which is a boric acid ester of a 5,6-dihydroxy indole derivative. R1 and R2 independently represent H, a C1-C10 substituted/unsubstituted alkyl group, a C6-C10 substituted/unsubstituted aryl group, an oxygen-containing group, or a halogen atom; R3 is H, or a C1-C10 substituted/unsubstituted alkyl group; R4 and R5 independently represent H or a C1-C12 aliphatic group, or integrally represent a C1-C4 alkylene group. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
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Paragraph 0080-0081
(2021/09/27)
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- Preparation method of 5, 6-methylenedioxy indole
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The invention provides a preparation method of 5, 6-methylenedioxy indole. The preparation method comprises the following steps: reacting 3, 4-methylenedioxy aniline serving as a raw material with benzene sulfonyl chloride to obtain A2, reacting A2 with 2, 2-dimethoxy-1-bromoethane to obtain a precursor A3 of a ring closing reaction, performing ring closing on A3 under the action of Lewis acid toobtain A4, and removing a protecting group of amino by using alkali to obtain the final 5, 6-methylenedioxy indole. according to the invention, 3, 4-methylenedioxy aniline is used as a raw material, nitro is prevented from being reduced into amino, the price of the compound is low, the cyclization reaction can be completed at normal temperature under the action of Lewis acid, and extreme conditions of high temperature or a strong reducing agent are avoided. The whole synthesis operation is simple, the post-treatment is easy, and the generated three wastes are few. The solvent in the reaction process can be reused, so that the cost is reduced, the operation is simple, the yield is higher, and the product with the purity of more than 98% can be obtained. The method is suitable for mass production and has obvious economic benefits.
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Paragraph 0036-0038
(2021/03/31)
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- SOLID FORMS OF 3-(5-FLUOROBENZOFURAN-3-YL)-4-(5-METHYL-5H-[1,3]DIOXOLO[4,5-F]INDOL-7-YL)PYRROLE-2,5-DIONE
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The present disclosure relates to solid forms of 3-(5-Fluorobenzofuran-3-yl)-4-(5-methyl-5H-[1,3]dioxolo[4,5-f]indol-7-yl) pyrrole-2,5-dione, processes for preparation thereof, pharmaceutical compositions thereof, and uses thereof in treating disease.
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Paragraph 0059
(2019/05/10)
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- COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS
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This invention relates to compounds, pharmaceutical compositions comprising them, and methods of using the compounds and compositions for treating bacterial infections. This invention relates more particularly to compounds and pharmaceutical compositions thereof, methods of inhibiting H2S-producing enzymes with the compounds, and methods of treating bacterial infections with the compounds.
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- SOLID FORMS OF 3-(5-FLUOROBENZOFURAN-3-YL)-4-(5-METHYL-5H[1,3]DIOXOLO[4,5-F]INDOL-7-YL)PYRROLE-2,5-DIONE
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The present disclosure relates to solid forms of 3-(5-Fluorobenzofuran-3-yl)-4-(5-methyl-5H-[1,3]dioxolo[4,5-f]indol-7-yl)pyrrole-2,5-dione, processes for preparation thereof, pharmaceutical compositions thereof, and uses thereof in treating disease.
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Paragraph 0122
(2019/02/25)
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- Tandem Wittig – Reductive annulation decarboxylation approach for the synthesis of indole and 2-substituted indoles
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A simple tandem Wittig reaction-reductive decarboxylation route is established for the synthesis of indoles from commercially available o-nitrobenzaldehydes and a stable phosphorane. The method allows access to indoles in a very fast manner without involving any metal or expensive reagents or inert atmosphere. Also 2-substituted indoles are obtained which forms an important core of many biological active compounds.
- Volvoikar, Prajesh S.,Tilve
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supporting information
p. 1851 - 1854
(2018/04/14)
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- Straight Access to Indoles from Anilines and Ethylene Glycol by Heterogeneous Acceptorless Dehydrogenative Condensation
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The development of original strategies for the preparation of indole derivatives is a major goal in drug design. Herein, we report the first straight access to indoles from anilines and ethylene glycol by heterogeneous catalysis, based on an acceptorless dehydrogenative condensation, under noninert conditions. In order to achieve high selectivity, a combination of Pt/Al2O3 and ZnO have been found to slowly dehydrogenate ethylene glycol generating, after condensation with the amine and tautomeric equilibrium, the corresponding pyrrole-ring unsubstituted indoles.
- Llabres-Campaner, Pedro Juan,Ballesteros-Garrido, Rafael,Ballesteros, Rafael,Abarca, Belén
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p. 521 - 526
(2018/01/01)
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- Catalytic synthesis method of indole compounds
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The invention discloses a catalytic synthesis method of indole compounds.The method includes the following steps of firstly, conducting stirring reaction on ortho-nitrostyrolene or derivatives of ortho-nitrostyrolene, bis(pinacolato)diboron, alkali and low-grade saturated monohydric alcohol under the atmosphere of nitrogen; secondly, cooling the reaction product in the first step to the room temperature, adding ethyl acetate to be sufficiently mixed, and washing with ethyl acetate after filtering; thirdly, spin-drying low-grade saturated monohydric alcohol in an organic phase of the material obtained in the second step, passing through a silica gel column, and drip washing the silica gel column with eluent composed of petroleum ether and ethyl acetate to obtain pure products, namely, the indole compounds.By means of the method, under the neutral conditions, bis(pinacolato)diboron low in price serves as the raw material, friendly low-grade saturated monohydric alcohol serves as the solvent, the indole compounds are obtained through simple operation, the raw materials are low in price and easy to obtain, efficiency and safety are high, and wide expandability and good industrial application prospects are achieved.
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Paragraph 0024; 0025; 0026; 0027; 0028; 0029; 0030; 0031
(2016/10/10)
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- Synthesis of indoles from o,β-dinitrostyrenes via indium/acetic acid-mediated Reductive heterocyclizations
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Reductive heterocyclization reactions of various 1-nitro-2-(2-nitroaryl) ethenes to indoles were investigated. In the presence of indium/AcOH in toluene or benzene, 1-nitro-2-(2-nitroaryl)ethenes were cyclized to give corresponding indoles in good yields.
- Lee, Geunsoo,Choi, Jaehwan,Lee, Byung Min,Kim, Byeong Hyo
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p. 155 - 162
(2013/03/13)
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- Phosphane-free Pd0-catalyzed cycloamination and carbonylation with Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3: Preparation of benzocyclic amines and benzolactams
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Phosphane-free Pd0-catalyzed intramolecular aromatic amination was studied. o-Halophenethylamines and 3-(o-halophenyl)propylamines were found to be transformed into indolines and quinolines in a catalytic system based on Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3. Application of the method to substrates containing isoquinoline rings- the 1-(o-bromobenzyl)-3,4-dihydroisoquinolines 6, the 1-(o-bromobenzyl)-1,2,3,4-tetrahydroisoquinolines 7, and the 1-(o-bromophenethyl)isoquinolines 9- provided the indolo[2,1-a]isoquinoline and dibenzo[a,f]quinolizine ring systems 8 and 10. Extension of the method to β-carbolines (compounds 11, 12, and 17) produced the benz[f]indolo[2,3-a] indolizine-13-ones 15 and the benz[f]indolo[2,3-a]quinolizine 18. The benzo[f]pyrido[3,4-a]indolizine and indolo[f]pyrido[3,4-a]indolizin-12-one ring systems 27 and 31 were built in a similar manner. It was also found that under an atmosphere of CO the same catalytic system produced the corresponding benzolactams, the isoquino[2,1-a][2,7]naphthyridine 34 and the indolo[2,3-a]pyrido[g]quinolizin-8-one 36 [(±)-dihydronauclefine] in good yields. Copyright
- Harada, Rika,Nishida, Naoto,Uchiito, Shiho,Onozaki, Yu,Kurono, Nobuhito,Senboku, Hisanori,Masao, Tokuda,Ohkuma, Takeshi,Orito, Kazuhiko
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p. 366 - 379
(2012/02/04)
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- Convenient modification of the Leimgruber-Batcho indole synthesis: Reduction of 2-nitro-p-pyrrolidinostyrenes by the FeCl3-activated carbon-N2H4H2O system
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A new catalytic system containing ferric chloride, activated carbon, and hydrazine has been proposed for the reductive cyclization of β-dialkylamino-2-nitrostyrenes to give the corresponding indoles (Leimgruber-Batcho synthesis). Various substituted indoles may be obtained in high yield under these conditions.
- Taydakov,Dutova,Sidorenko,Krasnoselsky
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experimental part
p. 425 - 434
(2012/01/13)
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- Indolocarbazole anticancer agents and methods of using same
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The present invention relates to anti-tumor compounds, compositions and methods. In particular, the invention relates to indolocarbazole analogues of the following general formulas that inhibit topoisomerase I activity. 1
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- Indolocarbazole anticancer agents and methods of using them
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The present invention relates to anti-tumor compounds, compositions and methods. In particular, the invention relates to indolocarbazole analogues of the following general formulas that inhibit topoisomerase I activity. 1
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- Process for dyeing keratinous fibres with indole derivatives combined with an iodide
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Process for dyeing human keratinous fibres, consisting in applying on these fibres at least least one composition (A) containing, in a cosmetically acceptable medium, one or more indole derivatives corresponding to the formula (I) STR1 in which: R1/
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- Synthesis and characterization of 5H-1,3-dioxolo[4,5-f]indoleethylamines
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Twelve new N,N-dialkylated-5,6-methylenedioxytryptamines and N-cyclopropyl-5,6-methylenedioxytryptamine were prepared as hybrids of known psychoactive phenylethylamines and tryptamines. Novel, more convenient synthesis of N-methyl- and N-benzylcyclopropyl
- Grotjahn
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p. 1031 - 1036
(2007/10/02)
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- Intermediates for indoles
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Ortho-nitrotoluenes are condensed with formamide acetals to yield the corresponding otho-nitro-β-aminestyrenes which undergo cyclization upon reduction to yield indoles.
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