- Iron(II)-catalyzed direct cyanation of arenes with aryl(cyano)iodonium triflates
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A direct oxidative cyanation of arenes under FeII catalysis with 3,5-di(trifluoromethyl)phenyl(cyano)iodonium triflate (DFCT) as the cyanating agent has been developed. The reaction is applicable to wide range of aromatic substrates, including polycyclic structures and heteroaromatic compounds. Copyright
- Shu, Zhibin,Ji, Wenzhi,Wang, Xi,Zhou, Yujing,Zhang, Yan,Wang, Jianbo
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supporting information
p. 2186 - 2189
(2014/03/21)
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- Practical one-pot transformation of electron-rich aromatics into aromatic nitriles with molecular iodine and aq NH3 using Vilsmeier-Haack reaction
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Various electron-rich aromatics could be efficiently transformed into the corresponding aromatic nitriles in good to moderate yields by treatment with DMF and POCl3, followed by the reaction with molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH) in aq NH3. Some of less reactive aromatics, such as anisole, 1,2-dimethoxybenzene, 1,4-dimethoxybenzene, and mesityrene, could be also transformed into the corresponding aromatic nitriles in good to moderate yields using N-methylformanilide and O(POCl 2)2, followed by the reaction with molecular iodine in aq NH3. Moreover, propiophenone derivatives could be successfully transformed into the corresponding β-chlorocinnamonitriles by the reaction with DMF and POCl3, followed by the reaction with molecular iodine and aq NH3. These reactions are novel metal-free one-pot methods for the preparation of aromatic nitriles from electron-rich aromatics and β-chlorocinnamonitriles from propiophenones.
- Ushijima, Sousuke,Moriyama, Katsuhiko,Togo, Hideo
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experimental part
p. 4588 - 4595
(2012/07/27)
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- Synthesis of 2-arylbenzoxazoles from flash vacuum pyrolysis of 2-methoxy-N-(arenylidene)anilines
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Flash vacuum pyrolysis of 2-methoxy-N-(arenylidene)anilines 2a-g at 700 °C and 1 × 10-2 Torr gave the corresponding 2-arylbenzoxazoles 1a-g.
- Chou, Chin-Hsing,Hsueh, Yu-Tan,Wang, Bo-Chi
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experimental part
p. 301 - 305
(2011/10/18)
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- Anthranilic acid derivatives as inhibitors of the cGMP-phosphodiesterase
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Compounds of formula (I) STR1where R 1 is hydrogen; R 2 is nitro, cyano or halo(lower)alkyl; R 3 is phenyl substituted with one or more substituents selected from halogen, cyano and lower alkoxy; A is a lower alkylene group; R 4 is a group CR 6 R 7 R 8 wherein R 6 and R 7 form, together with the carbon atom to which they are attached a cycloalkyl group optionally substituted with hydroxy, lower alkoxy or a lower alkanoylamino; and R 8 is hydrogen; its prodrug and a salt thereof.
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- Anodic Cyanation of Benzothiophenes
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The electrooxidation of benzothiophene and 2-methyl- and 3-methyl-benzothiophene was carried out in methanol containing sodium cyanide at a Pt anode in a divided cell.In all instances, heterocyclic ring-substitution products were obtained, together with minor amounts of addition products.With methylbenzothiophene, a small amount of side-chain-methoxylation product was also formed as a by-product.
- Yoshida, Kunihisa,Miyoshi, Kohji
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p. 333 - 336
(2007/10/02)
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- BEHAVIOUR OF CYCLOPROPANES BEARING CAPTO-DATIVE SUBSTITUTION UPON ELECTRON-IMPACT AND FLASH-VACUUM PYROLYSIS CONDITIONS
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Tandem mass spectrometry has been applied to investigate the behaviour of bis-captodative(cd) substituted cyclopropanes upon electron impact (EI) and flash-vacuum pyrolysis (FVP) comditions.Ring-opening of the molecular ions of 1 followed by a 1,2-hydrogen shift preceedes the fragmentation consisting mainly in the competitive losses of CH3S. and CH2S.The least energy demanding reaction is however a methyl loss requiring also ring cleavage.The m/z 70 base peak is ascribed to cyanothioacylium ions(NC-C=S(1+)) as indicated by the characteristic fragmentations induced by collision.Upon FVP conditions 1 decays to the cd olefin 8 and the carbene 9 in competition with the extrusion of CH3S. and CH3. radicals at the highest temperatures.The behaviour of 2 upon both conditions is dominated by the chemistry of the t-butyl substituents.Ring cleavage of the molecular ions of 3 preceedes also the fragmentation and induces rearrangement reactions yielding unexpected cyclohexadiene thione ions and C7H7(1+) ions.Upon FVP, C-S bond homolysis readily occurs in competition with an elimination of a carbene molecule.
- Chen, Lin-Zhi,Flammang, Robert,Maquestiau, Andre,Masamba, Wayiza,Merenyi, Robert,et al.
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p. 529 - 546
(2007/10/02)
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- Benzothiophenes and benzofurans and antiallergic use thereof
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Novel benzothiophene and benzofuran derivatives having antiallergic activity are described as well as a method of manufacture, pharmaceutical compositions, and methods of use therefor. The disclosure describes the use of derivatives for prevention of the release of mediators including histamine and leukotrienes from basophils and mast cells, and prevent respiratory burst in neutrophils providing activity useful in cardiovascular disorders as well as in antiinflammatory, psoriasis, and antimigraine treatment.
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