- Novel synthesis of benzofuran- and indol-2-yl-methanamine derivatives
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We report on a novel synthesis towards benzofuran-2-yl-methanamine and indol-2-yl-methanamine derivatives by using ortho-methoxy and ortho-nitro substituted phenylacetic acids as starting material, respectively. For each compound series, a key intermediate bearing the oxazole-4-carboxylic acid methylester moiety was produced. Refluxing the ortho-methoxy series in HBr/HAc produced the desired benzofuran-2-yl-methanamines. Accordingly, for the synthesis of indoles the nitro-group was first reduced and refluxing these intermediates in HCl gave the corresponding indol-2-yl-methanamines. The method worked well with electron donating substituents. Limitations regarding electron withdrawing substituents are discussed. This straightforward synthetic procedure can be a useful approach to generate a variety of substituted benzofuran-2-yl-methanamine and indol-2-yl-methanamine compounds by starting from readily available phenylacetic acid derivatives.
- Schlosser, Joachim,Johannes, Eugen,Zindler, Melanie,Lemmerhirt, Jan,Sommer, Benjamin,Schütt, Martin,Peifer, Christian
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- 8-Substituted 3,4-dihydroquinolinones as a novel scaffold for atypical antipsychotic activity
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Several new, potent dopamine subtype 2 (DA D2) active compounds with serotonin subtype 2A (5-HT2A) pharmacology are presented. 8-Substituted 3,4-dihydroquinolinones, tetrahydroquinolines, and N-acyl tetrahydroquinolines were evaluated in primary assays. Subtle changes on this novel scaffold translated to large changes in potency and selectivity in vitro. These compounds show promise as novel atypical antipsychotics for the treatment of schizophrenia.
- Singer, Jamie M.,Barr, Bridget M.,Coughenour, Linda L.,Gregory, Tracy F.,Walters, Michael A.
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p. 4560 - 4563
(2007/10/03)
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- An aminoisoflavone-salicyloylindole ring transformation
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A series of 2′-nitroisoflavones 8-10, 15, 22, 27 and 28 was prepared via the (2-nitro-phenyl)-acetic acids 1, 13, 19 and 25. In order to obtain the corresponding 2′-aminoisoflavones the reduction of 8-10, 15, 22, 27 and 28 was undertaken. Surprisingly, new 3-salicyloylindoles instead of the expected 2′-aminoisoflavones were the main reduction products. In the following paper the preparation of the 2′-nitroisoflavones 8-10, 15, 22, 27 and 28 as well as the reduction experiments obtaining the 2′-aminoisoflavones 33 and 35 and the 3-salicyloylindoles 29-32, 34 and 36 will be described. Furthermore, a possible mechanism responsible for the formation of the 3-salicyloylindoles from 2′-nitroisoflavones under reductive conditions will be discussed.
- Loewe, Werner,Witzel, Sonja,Tappmeyer, Silvia,Albuschat, Rica
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p. 317 - 326
(2007/10/03)
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- A Convergent Synthesis of 14-Membered F-O-G Ring Analogs of the Teicoplanin Binding Pocket via Intramolecular SNAr Reaction
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An intramolecular SNAr reaction for efficient macrocyclization via biaryl ether formation was developed for syntheses of the 14-membered macrocycles 2 and 3 related to F-O-G ring of teicoplanin 1.Chloride as well as fluoride could be used as the leaving group in this reaction.However, the latter was prefered since it required milder conditions.Both ortho and para nitro, fluoro disubstituted aromatic rings were suitable for the macrocyclization reaction with tethered aryl oxides.The nonproteinogenic α-amino acid 23, required for the synthesis of 3, was prepared via an asymmetric Strecker synthesis using (R)-phenylglycinol as a chiral auxiliary.The overall synthetic strategy was convergent, and the cyclization could be performed in the presence of the highly sensitive arylglycine unit without racemization.
- Zhu, Jieping,Beugelmans, Rene,Bourdet, Sebastien,Chastanet, Jacqueline,Roussi, George
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p. 6389 - 6396
(2007/10/03)
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