- Reaction of 2-naphthylamine with sodium iodate/sodium sulfite: Synthesis of 2-amino-1-iodonaphthalene
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The reaction of 2-naphthylamine with NaIO3/Na2SO 3/HCl yields exclusively 2-amino-1-iodonaphthalene and not regioisomer 2-amino-3-iodonaphthalene as was previously reported. The assigned structure is supported by spectroscopic data. Taylor & Francis Group, LLC.
- Taldone, Tony,Zatorska, Danuta,Chiosis, Gabriela
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- Photochemical Approach to the Cyclohepta[b]indole Scaffold by Annulative Two-Carbon Ring-Expansion
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We report on the implementation of the concept of a photochemically elicited two-carbon homologation of a π-donor–π-acceptor substituted chromophore by triple-bond insertion. Implementing a phenyl connector between the slide-in module and the chromophore enabled the synthesis of cylohepta[b]indole-type building blocks by a metal-free annulative one-pot two-carbon ring expansion of the five-membered chromophore. Post-irradiative structural elaboration provided founding members of the indolo[2,3-d]tropone family of compounds. Control experiments in combination with computational chemistry on this multibond reorganization process founded the basis for a mechanistic hypothesis.
- Tymann, Dina Christina,Benedix, Lars,Iovkova, Lyuba,Pallach, Roman,Henke, Sebastian,Tymann, David,Hiersemann, Martin
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p. 11974 - 11978
(2020/08/21)
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- Fluorene-containing organic compound as well as preparation method and application thereof in OLED (organic light emitting diode) device
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The invention discloses a fluorene-containing organic compound. The organic compound has the structure formula shown in the general formula (1). The compound has higher glass transition temperature and molecular heat stability, proper HOMO and LUMO energy levels and higher Eg, the photoelectric property of an OLED (organic light emitting diode) device can be effectively improved and the service life of the OLED device can be effectively prolonged through structure optimization of the device.
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- Two BN isosteres of anthracene: Synthesis and characterization
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The synthesis of two parental BN anthracenes, 1 and 2, was developed, and their electronic structure and reactivity behavior were characterized in direct comparison with all-carbon anthracene. Gas-phase UV-photoelecton spectroscopy studies revealed the following HOMO energy trend: anthracene, -7.4 eV; BN anthracene 1, -7.7 eV; bis-BN anthracene 2, -8.0 eV. The λmax of the lower energy band in the UV-vis absorption spectrum is as follows: anthracene, 356 nm; BN anthracene 1, 359 nm; bis-BN anthracene 2, 357 nm. Thus, although the HOMO is stabilized with increasing BN incorporation, the HOMO-LUMO band gap remains unchanged across the anthracene series. The emission λmax values for the three investigated anthracene compounds are at 403 nm. The pKa values of the N-H proton for BN anthracene 1 and bis-BN anthracene 2 were determined to be approximately 26. BN anthracenes 1 and 2 do not undergo heat- or light-induced cycloaddition reactions or Friedel-Crafts acylations. Electrophilic bromination of BN anthracene 1 with Br2, however, occurs regioselectively at the 9-position. The reactivity behavior and regioselectivity of bromination of BN anthracenes are consistent with the electronic structure of these compounds; i.e., (1) the lower HOMO energy levels for BN anthracenes stabilize the molecules against cycloaddition and Friedel-Crafts reactions, and (2) the HOMO orbital coefficients are consistent with the observed bromination regioselectivity. Overall, this work demonstrates that BN/CC isosterism can be used as a molecular design strategy to stabilize the HOMO of acene-type structures while the optical band gap is maintained.
- Ishibashi, Jacob S.A.,Marshall, Jonathan L.,Mazire, Audrey,Lovinger, Gabriel J.,Li, Bo,Zakharov, Lev N.,Dargelos, Alain,Graciaa, Alain,Chrostowska, Anna,Liu, Shih-Yuan
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p. 15414 - 15421
(2015/01/08)
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- PURINE DERIVATIVES USEFUL AS HSP90 INHIBITORS
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The present application provides substituted purine derivatives and related compounds of the formulas shown. These com ounds are useful as inhibitors of HSP90, and hence in the treatment of related diseases. (Formulae) Z1-Z3, Xa-Xc, X2, X4, Y and R are as defined in the specification.
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- 1-(2-Naphthyl)-1H-pyrazole-5-carboxylamides as potent factor Xa inhibitors. Part 2: A survey of P4 motifs
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A variety of P4 motifs have been examined to increase the binding affinity and in vitro anticoagulant potency of our biphenyl 1-(2-naphthyl)-1H-pyrazole-5- carboxylamide-based fXa inhibitors. Highly potent 2-naphthyl-P1 fXa inhibitors (Ki≤2 nM) with improved in vitro anticoagulant activity (2×TG≤1 μM) and respectable pharmacokinetic properties have been discovered.
- Jia, Zhaozhong J.,Wu, Yanhong,Huang, Wenrong,Zhang, Penglie,Clizbe, Lane A.,Goldman, Erick A.,Sinha, Uma,Arfsten, Ann E.,Edwards, Susan T.,Alphonso, Merlyn,Hutchaleelaha, Athiwat,Scarborough, Robert M.,Zhu, Bing-Yan
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p. 1221 - 1227
(2007/10/03)
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- Synthesis and biological evaluation of A-ring biaryl-carbamate analogues of rhazinilam
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An improvement of the synthesis of biphenyl-carbamate 2a, the most active analogue of rhazinilam 1 so far, was performed using the Pd-catalyzed borylation/Suzuki coupling (BSC) method developed in our laboratories. The preparation of A-ring analogues of 2a bearing electron-withdrawing or donating groups is reported according to this new synthetic scheme. The antitubulin properties as well as the cytotoxicity of these compounds toward human cancer cell lines were evaluated in comparison with rhazinilam and 2a.
- Baudoin, Olivier,Claveau, Fabien,Thoret, Sylviane,Herrbach, Audrey,Guenard, Daniel,Gueritte, Francoise
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p. 3395 - 3400
(2007/10/03)
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- Efficient asymmetric synthesis of biologically important tryptophan analogues via a palladium-mediated heteroannulation reaction
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A novel and concise synthesis of optically active tryptophan derivatives was developed via a palladium-catalyzed heteroannulation reaction of substituted o-iodoanilines with an internal alkyne. The required internal alkyne 14a or 25 was prepared in greater than 96% de via alkylation of the Schoellkopf chiral auxiliary 19 employing diphenyl phosphate as the leaving group. The Schoellkopf chiral auxiliary was chosen here for the preparation of L-tryptophans would be available from D-valine while the D-isomers required for natural product total synthesis would originate from the inexpensive L-valine (300-g scale). Applications of the palladium-catalyzed heteroannulation reaction were extended to the first asymmetric synthesis of L-isotryptophan 38 and L-benz[f]tryptophan 39. More importantly, the optically pure 6-methoxy-D-tryptophan 62 was prepared by this protocol on a large scale (>300 g). This should permit entry into many ring-A oxygenated indole alkaloids when coupled with the asymmetric Pictet-Spengler reaction. In addition, an improved total synthesis of tryprostatin A (9a) was accomplished in 43% overall yield employing this palladium-mediated process.
- Ma,Liu,Li,Flippen-Anderson,Yu,Cook
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p. 4525 - 4542
(2007/10/03)
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- Efficient asymmetric synthesis of important tryptophan analogs for biological research via the Schollkopf chiral auxiliary
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An efficient method has been developed via the Schollkopf chiral auxiliary for the asymmetric synthesis of the important tryptophan analogs: L-isotryptophan, L-benzo[f]tryptophan and L-homotryptophan. (C) 2000 Elsevier Science Ltd.
- Ma, Chunrong,Yu, Shu,He, Xiaohui,Liu, Xiaoxiang,Cook, James M.
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p. 2781 - 2785
(2007/10/03)
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