- Synthesis of pyrazolo[1,5- c] quinazoline derivatives through the copper-catalyzed domino reaction of o -alkenyl aromatic isocyanides with diazo compounds
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A novel copper-catalyzed domino reaction between o-alkenyl aromatic isocyanides and diazo compounds has been developed under mild reaction conditions. Various o-alkenyl aromatic isocyanides were prepared from readily available reactants. The reaction prov
- Li, Lei,Liu, Lu,Mao, Shukuan,Wang, He,Wang, Xin,Zhao, Yu-Long,Zhou, Ming-Dong
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- Bisannulation of 2,3-dichloro-1,4-naphthoquinone with o-nitrophenylacetic acid derivatives: A succinct synthesis of the ABCD ring system of alpkinidine
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Three bisannulation strategies have been used to rapidly construct pentacyclic benzo-fused pyrrolo[4,3,2-mn]acridines, similar to several biologically active natural products. The key steps involve Michael substitution of 2,3-dichloro-1,4-naphthoquinone w
- Buccini, Marco,Jeow, Shi Yuan,Byrne, Lindsay,Skelton, Brian W.,Nguyen, Tuan Minh,Chai, Christina L. L.,Piggott, Matthew J.
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Read Online
- Mn(III)-Mediated Radical Cyclization of o-Alkenyl Aromatic Isocyanides with Boronic Acids: Access to N-Unprotected 2-Aryl-3-cyanoindoles
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The synthesis of N-unprotected 2-aryl-3-cyanoindoles was realized via the Mn(III)-mediated radical cascade cyclization of o-alkenyl aromatic isocyanides with boronic acids. A possible mechanism involving a sequential intermolecular radical addition, intramolecular cyclization, and cleavage of the C-C bond under mild reaction conditions is proposed. Mechanism studies show that H2O or O2 might provide the oxygen source for the elimination of benzaldehyde.
- Liu, Lu,Li, Lei,Wang, Xin,Sun, Ran,Zhou, Ming-Dong,Wang, He
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supporting information
p. 5826 - 5830
(2021/08/18)
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- Trifluoromethylation/Difluoromethylation-Initiated Radical Cyclization of o-Alkenyl Aromatic Isocyanides for Direct Construction of 4-Cyano-2-Trifluoromethyl/Difluoromethyl-Containing Quinolines
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In this study, a radical-triggered cyclization of o-alkenyl aromatic isocyanides prepared from accessible starting materials is developed. The reaction provides a general and efficient method for the synthesis of 4-CN-2-CF3/CF2H-cont
- Li, Lei,Liu, Lu,Mao, Shukuan,Wang, He,Wang, Xin,Zhou, Ming-Dong
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supporting information
(2020/05/25)
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- CASPASE INHIBITOR AND PHARMACEUTICAL COMPOSITION, USE AND THERAPEUTIC METHOD THEREOF
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Disclosed are a class of compounds as a caspase inhibitor, and in particular the compound as shown in formula (I) or a pharmaceutically acceptable salt thereof, and the use of the compound in treating caspase-related diseases.
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Paragraph 0300; 0301
(2019/04/05)
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- Method for preparing indole and derivatives thereof
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The invention discloses a method for preparing indole and derivatives of indole. The method for preparing indole and the derivatives of indole is characterized by comprising the following two steps that (1) a catalyst, a ligand and alkali are added in a reaction tube, under the protection of nitrogen, beta-hydroxy ketone or ester is reacted with a mixed solution of o-nitro aryl halides for 3 to 8h in an oil bath pan at the temperature of 90 to 120 DEG C, and then cooled to room temperature after reaction, and extracted, washed, dried and subjected to chromatography to obtain a product of o-nitro alpha-aryl ketone or ester; (2) o-nitro alpha-aryl ketone or ester obtained in the step (1), a reducing agent system and a solvent are added to the reaction tube, and reacted for 3 to 8h at the temperature of 60 to 100 DEG C, and then extracted, washed, dried and subjected to chromatography after being reacted to obtain a target product of indole and the derivatives of indole. Reaction raw materials, the catalyst, the ligand, the alkali and the solvent used in the invention are all industrial commodities, and simple and readily available, wide in sources, cheap in price, and further very stable in performances, and with no need for special storage conditions; in addition, the method for preparing indole and the derivatives of indole disclosed by the invention has the characteristics of low cost, high yield, simple process, less pollution and the like.
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Paragraph 0077-0081
(2017/08/24)
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- C-C Activation by Retro-Aldol Reaction of Two β-Hydroxy Carbonyl Compounds: Synergy with Pd-Catalyzed Cross-Coupling to Access Mono-α-arylated Ketones and Esters
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A retro-aldol reaction of two β-hydroxy compounds in synergy with Pd-catalyzed cross-coupling of aryl halides is reported herein, which produces selectively mono-α-arylated ketones and esters in good yields. This reaction is compatible with a broad range of aryl iodides, bromides, chlorides, and triflates and can tolerate an array of functional groups on the aromatic ring. Ready scale-up of this reaction to gram level is applicable without an appreciable decrease in the reaction yield. Furthermore, concise syntheses of biologically active isocoumarin and indole derivatives have been achieved to greatly demonstrate the synthetic value of this retro-aldol reaction. Finally, the reaction mechanism has been discussed on the basis of experimental observations and DFT computational results. A regulated six-membered-ring transition structure has been located for the key retro-aldol C-C cleavage, which constitutes the rate-determining step of a full catalytic cycle. The concept of C-C activation by retro-aldol reaction may also find applications in other fundamental reactions.
- Zhang, Song-Lin,Yu, Ze-Long
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- Divergent synthesis of indoles, oxindoles, isocoumarins and isoquinolinones by general Pd-catalyzed retro-aldol/α-arylation
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Divergent synthesis of indoles, oxindoles, isocoumarins and isoquinolinones is described in this report by using a general Pd-catalyzed tandem reaction of β-hydroxy carbonyl compounds with aryl halides bearing an ortho-nitro, -ester or -cyano substituent. A key retro-aldol/α-arylation reaction is involved that merges classic Pd cross-coupling chemistry with novel Pd-promoted retro-aldol C-C activation to produce α-arylated ketones or esters. Subsequent intramolecular condensation of the carbonyl with the ortho-synthon gives target heterocycles. The use of common, commercially available and cheap substrates and catalyst system adds additional synthetic advantages to the conceptual significance.
- Zhang, Song-Lin,Yu, Ze-Long
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supporting information
p. 10511 - 10515
(2016/11/18)
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- METHOD FOR TREATING VIRUS INFECTION USING DERIVATIVE OF ANILINE
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A method for treating a virus infection in a subject is provided. The method comprising administering to the subject in need an effective amount of a derivative of aniline selected from the group consisting of a compound of formula (I), a pharmaceutically
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Paragraph 0069
(2015/07/15)
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- Synthesis, structural characterisation, and preliminary evaluation of non-indolin-2-one-based angiogenesis inhibitors related to sunitinib (Sutent)
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The indolin-2-one fused-ring system and the 2,4-dimethylpyrrole unit represent key structural motifs in the anticancer drug sunitinib (Sutent) and predecessor angiogenesis inhibitors that have undergone anticancer clinical trials (e.g. semaxanib, SU5416). In pursuit of novel anti-angiogenic scaffolds, we were interested in identifying whether the indolin-2-one group in these structures could be modified without losing activity. This paper describes novel condensation chemistry used to prepare a test series of (E)-and (Z)-alkenes related to SU5416 that retain the 2,4-dimethylpyrrole unit while incorporating ring-opened indolin-2-ones. Unique structural characteristics were identified in the compounds, such as intramolecular hydrogen bonds in the (Z)-alkenes, and several examples were shown to possess significant anti-angiogenic activity in a rat aorta in vitro model of angiogenesis. The work demonstrates that the indolin-2-one moiety is not an absolute requirement for angiogenesis inhibition in the sunitinib/SU5416 class.
- Sudta, Pichit,Kirk, Nicholas,Bezos, Anna,Gurlica, Anthony,Mitchell, Rhys,Weber, Thomas,Willis, Anthony C.,Prabpai, Samran,Kongsaeree, Palangpon,Parish, Christopher R.,Suksamrarn, Sunit,Kelso, Michael J.
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p. 864 - 873
(2013/09/12)
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- VLA-4 INHIBITORS
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The present invention relates to a compound represented by the following formula (I): (wherein, W represents WA-A1 -WB - (in which, WA is substituted or unsubstituted aryl, etc., A1 is -NR1-, single bond, -C(O)-, etc., and WB is substituted or unsubstituted arylene, etc.), R is single bond, -NH-, -OCH2-, alkenylene, etc., X is -C(O) -CH2-, etc., and M is, for example, the following formula: (in which, R11, R12 and R13 each independently represents hydrogen, hydroxyl, amino, halogen, etc., R14 is hydrogen or lower alkyl, Y represents -CH2-O-, etc., Z is substituted or unsubstituted arylene, etc., A2 is single bond, etc, and R10 is hydroxyl or lower alkoxy)), or salt thereof; and a medicament containing the same. This compound or salt thereof selectively inhibits binding of cell adhesion molecules to VAL-4 and exhibits high bioavailability so that it is useful as a preventive and/or remedy for inflammatory diseases, autoimmune diseases, metastasis, bronchial asthma, rhinostenosis, diabetes, and the like.
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- 1,2-disubstituted-6-oxo-3-phenyl-piperidine-3-carboxamides and combinatorial libraries thereof
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The invention relates to combinatorial libraries containing two or more novel piperidine-3-carboxamide derivative compounds, methods of preparing the piperidine-3-carboxamide derivative compounds and piperidine-3-carboxamide derivative compounds bound to a resin
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- Experiments on the Chaperon effect in the nitration of aromatics
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A nitro group may be effectively delivered to the ortho position of alkylbenzenes, provided that a suitable chaperon function is located in α- position and a dilute of HNO3 in CH2Cl2 is used. The carbonyl function of an aldehyde or ketone is the best choice, but a carboxyl, alkoxycarbonyl, and amide groups all work well. The ether function showed a less pronounced ortho orientation effect, whereas the hydroxyl group was too prone to oxidation. Side reactions were minimal under the conditions employed. A para chaperon effect was seemingly at work in the CH2Cl2 nitration of benzenepropanenitrile. All the results were compared with the corresponding classical nitration in H2SO4.
- Strazzolini, Paolo,Giumanini, Angelo G.,Runcio, Antonio,Scuccato, Massimo
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p. 952 - 958
(2007/10/03)
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- Practical synthesis of 1H-indazole-3-carboxylic acid and its derivatives
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A practical and convenient synthesis of 1H-indazole-3-carboxylic acid and its amide and ester derivatives from the corresponding derivatives of 2-nitrophenylacetic acid was described.
- Yoshida, Toyokichi,Matsuura, Noriyasu,Yamamoto, Katsuhisa,Doi, Masahiro,Shimada, Kanji,Morie, Toshiya,Kato, Shiro
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p. 2701 - 2712
(2007/10/03)
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- Ozone-mediated nitration of phenylalkyl ethers, phenylacetic esters, and related compounds with nitrogen dioxide. the highest ortho substitution observed in the electrophilic nitration of arenes
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By the combined action of ozonized oxygen and nitrogen dioxide (the kyodai-nitration), the title compounds were smoothly nitrated in dichloromethane at subzero degrees with hiigh ortho positional selectivity. Although the conventional nitration of phenylacetic acid and esters mainly produces m- and p-nitro derivatives, the present nitration offers a simple high-yield synthesis of o-nitro derivatives which are important as precursor in organic synthesis. The proportions of the ortho isomer in the nitration products from methyl 2-phenylethyl ether and methyl phenylacetate were 71 and 88%, respectively, the latter value being the highest ortho isomer proportion so far observed in the electrophilic aromatic nitration. The observed high ortho selectivity has been rationalized in terms of radical cation intermediate and six-membered cyclic transition state.
- Suzuki, Hitomi,Takeuchi, Toyomi,Mori, Tadashi
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p. 5944 - 5947
(2007/10/03)
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- The Scope and Mechanism of a Novel Synthesis of 3,4-Fused Isoxazoles
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Thermal cyclisation of 2-nitrophenyl- and 3-nitrohetaryl-ethanoate derivatives in xylene is facilitated indirectly by 5 Angstroem molecular sieves affording an efficient general method for the construction of synthetically useful 3,4-fused isoxazoles; evidence for the mechanism of these novel heterocyclisation reactions is presented.
- Duffy, Kevin J.,Tennant, George
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p. 2457 - 2460
(2007/10/03)
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- Benzisoxazole- and Benzisothiazole-3-carboxamides as Potential Atypical Antipsychotic Agents
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A series of benzisoxazole- and benzisothiazole-3-carboxamides has been prepared and tested for potential antipsychotic activity.In general, the compounds showed an affinity for dopamine D2 and serotonin 5HT2A and 5HT1A rec
- Hrib, Nicholas J.,Jurcak, John G.,Burgher, Kendra L.,Conway, Paul G.,Hartman, Harold B.,et al.
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p. 2308 - 2314
(2007/10/02)
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