- Synthesis of Tetrahydrothiopyrano[2,3-b]indole [60]Fullerene Derivatives via Hetero-Diels–Alder Reaction of C60 and α,β-Unsaturated Indole-2-thiones
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Hetero-Diels–Alder reactions of [60]fullerene with α,β-unsaturated thio-oxindoles (3a, 3b, 3c), prepared from thio-oxindole 1 and heteroaromatic aldehydes (2a, 2b, 2c), to generate tetrahydrothiopyrano[2,3-b]indole [60]fullerene cycloadducts (5a, 5b, 5c) under thermal or microwave irradiation were described. The yields were improved, and the reaction time was decreased by conducting the reaction under microwave irradiation.
- Matloubi Moghaddam, Firouz,Ghanbari, Bahram,Behzadi, Masoumeh,Baghersad, Mohammad Hadi
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- Heterocyclic Aromatic Anions with 4n + 2 ?-Electrons
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Equilibrium acidities in DMSO for several cyclic carboxamides, thiocarboxamides, esters, and sulfones that form anions possessing 4n + 2 electrons have been measured.Aromatic stabilization energies (ASEs) for these anions have been estimated by comparing
- Bordwell, Frederick G.,Fried, Herbert E.
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- Difluorocarbene-triggered cyclization: Synthesis of (hetero)arene-fused 2,2-difluoro-2,3-dihydrothiophenes
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An efficient method for the synthesis of (hetero)arene-fused 2,2-difluoro-2,3-dihydrothiophene derivatives using readily available sodium chlorodifluoroacetate (ClCF2CO2Na) has been developed. This transformation is achieved through a combination of a thi
- Liang, Huamin,Liu, Ran,Zhou, Min,Fu, Yue,Ni, Chuanfa,Hu, Jinbo
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supporting information
p. 7047 - 7051
(2020/09/15)
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- Nickel(ii)-catalyzed asymmetric thio-Claisen rearrangement of α-diazo pyrazoleamides with thioindoles
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A nickel(ii) catalyzed enantioselective thio-Claisen rearrangement of α-diazo pyrazoleamides with thioindoles was realized with modified chiral N,N′-dioxide ligands, affording a variety of C3-substituted indole derivatives in high yields (up to 95%) with excellent enantioselectivities (up to 96% ee) under mild reaction conditions. A possible transition state model was proposed based on previous reports and the X-ray crystal structure of the catalyst.
- Yang, Wei,Lin, Xiaobin,Zhang, Yongyan,Cao, Weidi,Liu, Xiaohua,Feng, Xiaoming
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supporting information
p. 10002 - 10005
(2020/09/15)
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- Copper-catalyzed synthesis of 2-sulfenylindoles from indoline-2-thiones and aryl iodides
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A novel and efficient method for synthesis of 2-sulfenylindole via copper-catalyzed coupling reaction of indoline-2-thiones with aryl iodides has been developed. A series of N-substituted and N-free 2-sulfenylindole were obtained in high yields. Furthermo
- Zhou, Shiping,Xiao, Genhua,Liang, Yun
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supporting information
p. 338 - 341
(2017/01/03)
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- Optically active thiophenes via an organocatalytic one-pot methodology
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A general methodology for the synthesis of trisubstituted, optically active thiophenes by an organocatalytic one-pot reaction cascade is presented. The target products are synthesized in good yields (up to 92%) and with excellent enantioselectivities (up to 98% ee). Importantly, based on practical and easily available starting materials, the presented methodology can be conducted under mild reaction conditions. To further elucidate the generality, the synthesis of optically active thienoindoles, as well as selenophenes, is also demonstrated.
- Ransborg, Lars Krogager,Albrecht, Lukasz,Weise, Christian F.,Bak, Jesper R.,Jorgensen, Karl Anker
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supporting information; experimental part
p. 724 - 727
(2012/04/11)
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- Highly efficient synthesis of thieno[2,3-b]indole derivatives
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Thieno[2,3-b]indole derivatives were efficiently prepared via the reaction of 1,3-dihydro-2H-indole-2-thiones with α-bromo-substituted ketones or aldehydes and in the presence of Et3N (Scheme 2 and Table). The reaction took place under very mil
- Boeini, Hassan Zali
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experimental part
p. 1268 - 1272
(2009/10/16)
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- Concise syntheses of the cruciferous phytoalexins brassilexin, sinalexin, wasalexins, and analogues: Expanding the scope of the Vilsmeier formylation
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(Chemical Equation Presented) Efficient syntheses of the phytoalexins brassilexin, sinalexin, and analogues are demonstrated through the application of the Vilsmeier formylation to indoline-2-thiones followed by a new aqueous ammonia workup procedure. Similarly, a very concise two-pot synthesis of the phytoalexins wasalexins using sequential formylation-amination of indolin-2-ones is described. Remarkably, this novel aqueous ammonia workup allows the sequential one-pot formylation-amination, expanding substantially the scope of the Vilsmeier formylation of both indoline-2-thiones and indolin-2-ones. The examination of the formylation-amination reaction and optimization of conditions, as well as the syntheses and antifungal activities of several brassilexin analogues, are reported.
- Pedras, M. Soledade C.,Jha, Mukund
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p. 1828 - 1834
(2007/10/03)
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- Carboxylic acid amide enols: Keto-enol/enolate interconversion of N-methylindoline-2-one and its 2-thione and 2-selone analogs in aqueous solution
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Carbon-acid ionization constants, Q(a)(K) (concentration quotiem at ionic strength = 0.10 M), were determined by spectrophotometric titration in aqueous solution for N- methylindoline-2-one, pQ(a)(K) = 15.70, N-methylindoline-2-thione, pQ(a)(K) = 8.93, and N-methylindoline-2-selone, pQ(a)(K) = 7.25. Rate profiles were also constructed for the thione and selone. These were interpreted, with support from the form of acid-base catalysis as well as solvent and substrate isotope effects, as representing keto - enol/enolate ion interconversion. That led to the enol acidity constant pQ(a)(E) = 4.05 and the keto-enol equilibrium constant pK(E) = 4.88 for the thione and estimates of the limits on these quantities, pQ(a)(E) 4, for the selone.
- Kresge, A. Jerry,Meng, Qingshui
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p. 1528 - 1536
(2007/10/03)
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- Tyrosine kinase inhibitors. 3. Structure-activity relationships for inhibition of protein tyrosine kinases by nuclear-substituted derivatives of 2,2'-dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamide)
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A series of indole-substituted 2,2'-dithiobis(1-methyl-N-phenyl-1H- indole-3-carboxamides) were prepared and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60(v-src) tyrosine kinase. The compounds were synthesized by conversion of appropriate 1-methyloxindoles to 1-methyl-2-indolinethiones with P2S5 followed by subsequent reaction with NaH and phenyl isocyanate and oxidative dimerization of the resulting 2,3- dihydro-N-phenyl-2-thioxo-1H-indole-3-carboxamides. The parent compound and many of the substituted analogues were moderately potent inhibitors of both kinase enzymes, but no clear relationships were seen between substitution on the indole ring and inhibitory activity. While 4-substituted compounds were generally inactive, 5-substituted derivatives with electron-withdrawing groups showed inhibitory activity. However, none of the substituted compounds showed significantly better activity than the unsubstituted parent compound. There was generally a good correlation between activity against the EGFR and pp60(v-src) kinases, but several compounds did show some specificity (>20- fold) of inhibition; 5-Cl and 5-Br derivatives preferentially inhibited pp60(v-src), while the 5-CF3 compound preferentially inhibited EGFR. Selected compounds from the series were found to inhibit the growth of Swiss 3T3 fibroblasts with IC50s in the range 2-25 μM, the most active being 4- substituted derivatives. The compounds inhibited bFGF-mediated protein tyrosine phosphorylation in intact cells more effectively than EGFR- or PDGF- mediated phosphorylation.
- Rewcastle,Palmer,Dobrusin,Fry,Kraker,Denny
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p. 2033 - 2042
(2007/10/02)
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- LITHIATION ROUTES TO OXINDOLES AND 2-INDOLINETHIONES: PRECURSORS TO 2,2'-DITHIOBISINDOLES WITH TYROSINE KINASE INHIBITORY PROPERTIES
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N-Substituted oxindoles and 2-indolinethiones can be prepared by lithiation of carboxyl protected N,2-dimethylanilines followed by quenching with CO2 or CS2 respectively. 2-Indolinethione derivatives are also available via demethylation of 2-methylthioindoles, which are prepared by lithiation of N-substituted indoles and treatment with dimethyl disulfide.
- Rewcastle, Gordon W.,Denny, William A.
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p. 701 - 708
(2007/10/02)
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- Novel tricyclic indole compound
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The invention relates to compounds of general formula: STR1 in which A, B, G, D which may be identical or different, each denote a hydrogen atom or a halogen atom, a lower alkoxy group or alternatively a lower alkyl group optionally substituted with one or more halogen atoms, X denotes a hydrogen atom, a linear or branched lower alkyl group or a group SO2 E in which E denotes a linear or branched lower alkyl group or an aryl group optionally substituted with a linear or branched lower alkyl group, T denotes a hydrogen atom or a lower alkyl group, R3 denotes a hydrogen atom or a linear or branched lower alkyl group or an aryl group optionally substituted with one or more linear or branched lower alkyl groups, n and m, which may be identical or different, each denote 0 or 1, R1 and R2, which may be identical or different, each denote a hydrogen atom or a linear or branched lower alkyl group, or alternatively, R1 and R2 form, together with the nitrogen atom to which they are linked, a saturated or unsaturated, mono- or bicyclic nitrogenous heterocyclic system, each ring being 5- or 6-membered and optionally comprising one or two other hetero atoms selected from nitrogen, oxygen or sulfur, and optionally substituted with one or more linear or branched lower alkyl or alkoxy groups or with an aryl group which is itself optionally substituted with one or more lower alkyl, lower alkoxy or trifluoromethyl groups or alternatively one or more halogen atoms, or alternatively, R1 denotes a group STR2 in which R4, R5 and R6, which may be identical or different, each denote a hydrogen atom or a linear or branched lower alkyl group, or alternatively R4 forms with R5 a bridge (CH2)p, p being between 2 and 4, or alternatively R1 denotes a dibenzo[a,d]cyclohept-5-yl group and R2 denotes a hydrogen atom, where appropriate, their isomers and also their addition salts with a pharmaceutically acceptable acid. Medicinal products.
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- Thermal Rearrangements of N-Aryl-1-alkynesulphenamides into Indoline-2-thiones
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Reaction of bromomagnesium benzenamides with 1-alkynyl thiocyanates affords the title sulphenamides.On heating in benzene, these sulphenamides undergo -sigmatropic rearrangements followed by cyclisation of the intermediate thioketenes yielding indoli
- Baudin, J.-B.,Bekhazi, M.,Julia, S. A.,Ruel, O.,Jong, R. L. P. de,Brandsma, L.
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p. 956 - 958
(2007/10/02)
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