- 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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- β-Amino alcohols from anilines and ethylene glycol through heterogeneous Borrowing Hydrogen reaction
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Borrowing Hydrogen (BH), also called Hydrogen Autotransfer (HA), reaction with neat ethylene glycol represents a key step in the preparation of β-amino alcohols. However, due to the stability of ethylene glycol, mono-activation has rarely been achieved. Herein, a combination of Pd/C and ZnO is reported as heterogeneous catalyst for this BH/HA reaction. This system results in an extremely air and moisture stable, and economic catalyst able to mono-functionalize ethylene glycol in water, without further activation of the diol. In this work, different diols and aromatic amines have been explored affording a new approach towards amino alcohols. This study reveals how the combination of two solid species can afford interesting catalytic properties in heterogeneous phase. ZnO activates ethylene glycol while Pd/C is the responsible of the BH/HA cycle. This catalytic system has also been found useful to dehydrogenate indoles affording indolines that undergo in situ BH/HA cycle prior to re-aromatization, representing a tandem heterogeneous process.
- Llabres-Campaner, Pedro J.,Ballesteros-Garrido, Rafael,Ballesteros, Rafael,Abarca, Belén
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supporting information
p. 5552 - 5561
(2017/08/22)
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- Heterogeneous borrowing hydrogen reactions with Pd/C and ZnO: Diol scope
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A borrowing hydrogen reaction with different diols was employed for the preparation of complex beta- gamma- or epsilon-amino alcohols from p-toluidine and tetrahydroquinoline with the aim of better understanding the applicability of the Pd/C ZnO heterogeneous catalyst.
- Llabres-Campaner, Pedro J.,Woodbridge-Ortega, Patricia,Ballesteros-Garrido, Rafael,Ballesteros, Rafael,Abarca, Belén
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supporting information
p. 4880 - 4882
(2017/11/29)
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- METHOD FOR PRODUCING TRICYCLIC HETEROCYCLIC COMPOUND
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It is an object of the present invention to provide a method for producing a high-purity tricyclic heterocyclic compound represented by formula (I), which is useful as a production intermediate for a pharmaceutical agent, wherein the method is an efficient production method with short steps and with a high yield, which does not use, as raw materials, expensive bromopyruvate and highly harmful copper chromite, and does not need silica gel column chromatography that generates, as by-products, large quantities of waste. The present invention relates to production of Compound (I) by the following method.
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Paragraph 0064
(2016/06/06)
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- COMBINATIONAL COMPOSITIONS AND METHODS FOR TREATMENT OF CANCER
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The present invention provides methods of treating a cell proliferative disorder, such as a cancer, by administering to a subject in need thereof a therapeutically effective amount of a pyrroloquinolinyl-pyrrole-2,5-dione compound or a pyrroloquinolinyl-pyrrolidine-2,5-dione compound in combination with a therapeutically effective amount of a second anti-proliferative agent.
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- An efficient one pot transfer hydrogenation and N-alkylation of quinolines with alcohols mediated by Pd/C/Zn
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A Pd/C/Zn mixture with alcohols has been revealed to be an efficient transfer hydrogenation system to quinolines. Furthermore, the metals mixture is able to activate alcohols as N-alkylating agents in a hydrogen autotransfer process. 1,2,3,4-Tetrahydroquinolines and N-alkylated tetrahydroquinolines from quinolines have been obtained with excellent yields in one step.
- Abarca, Belen,Adam, Rosa,Ballesteros, Rafael
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experimental part
p. 1826 - 1833
(2012/04/23)
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- MELEIMIDE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS AND METHODS FOR TREATMENT OF CANCER
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The present invention relates to pyrroloquinolinyl-pyrrole-2,5-dione compounds and pyrroloquinolinyl-pyrrolidine-2,5-dione compounds, and methods of preparation of these compounds. The present invention also relates to pharmaceutical compositions comprising pyrroloquinolinyl-pyrrole-2,5-dione compounds and pyrroloquinolinyl-pyrrolidine-2,5-dione compounds. The present invention provides methods of treating a cell proliferative disorder, such as a cancer, by administering to a subject in need thereof a therapeutically effective amount of a pyrroloquinolinyl-pyrrole-2,5-dione compound or pyrroloquinolinyl-pyrrolidine-2,5-dione compound of the present invention.
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Page/Page column 52
(2008/06/13)
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- PURINE DERIVATIVES AS KINASE INHIBITORS
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The present invention provides kinase inhibitors of Formula I.
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Page/Page column 24-25
(2008/06/13)
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- Radical cyclisation reactions of 7-bromoindoles
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The synthesis and radical cyclisation of 7-bromoindoles carrying an unsaturated N-alkyl group is described.
- Dobbs, Adrian P.,Jones, Keith,Veal, Ken T.
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p. 5379 - 5382
(2007/10/03)
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- Fischer indolization of N(α)-alkyl-2-allylphenylhydrazones
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Fischer indolization of the hydrazones of 8-allyl-1-amino-1,2,3,4-tetrahydroquinoline and related compounds was investigated. Fischer indolization induced Cope rearrangement of the allyl group and acid-catalyzed intramolecular cycloaddition between the hydrazonyl group and the vinyl group. The base treatment of the latter reaction product caused eliminative ring-opening of the adduct and led to the formation of an indoline skeleton bearing a 2-ketoalkyl group at the C-2 position.
- Katayama,Takatsu,Takeuchi,Yamagiwa
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p. 816 - 821
(2007/10/02)
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- Development of high-affinity 5-HT3 receptor antagonists. Structure- affinity relationships of novel 1,7-annelated indole derivatives. 1
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On the basis of the structures of ondansetron and GR 65,630, its ring- opened C-linked methylimidazole analogue, novel 1,7-annelated indole derivatives were synthesized as potential 5-HT3 antagonists. Receptor binding studies show that all compounds display a high affinity for the 5- HT3 receptors. In both series annelation results in compounds being 7 and 4 times more potent than the references ondansetron and GR 65,630, respectively. Similar to ondansetron, the 1,7-annelated indoles show little stereoselectivity. The (-)-isomers are only slightly more potent than the (+)-isomers. The receptor binding profile of l-10-[(2-methyl-1H-imidazol-1- yl)methyl]-5,6,8,9,10,11-hexahydro-4H-pyrido[3,2,1-jk]carbazol-11-one hydrochloride (24b) (INN cilansetron) shows that the compound displays, besides a high affinity for 5-HT3 receptors (K(i) = 0.19 nM), a weak affinity for σ-receptors (K(i) = 340 nM), muscarine M1 receptors (K(i) = 910 nM), and 5-HT4 receptors (K(i) = 960 nM) and no affinity (K(i) ≥ 5000 nM) for all the other receptor types tested (n = 37). The new compounds fit the proposed necessary chemical template for binding: a heteroaromatic ring system, a coplanar carbonyl group, and a nitrogen center at well-defined distances. The enhanced potency of the annelated 1,7-indole derivatives indicates that the extra ring provides a favorable hydrophobic area for interaction with the 5-HT3 receptor site. In vivo cilansetron is more potent and induces less central side effects than ondansetron. At present cilansetron is in clinical trials.
- Van Wijngaarden,Hamminga,Van Hes,Standaar,Tipker,Tulp,Mol,Olivier,De Jonge
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p. 3693 - 3699
(2007/10/02)
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