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1.
Kazuhiro Kobayashi Hiroo Hashimoto Teruhiko Suzuki Hisatoshi Konishi 《Helvetica chimica acta》2011,94(11):2002-2009
An efficient method for the synthesis of 2‐aryl‐2,3‐dihydro‐3‐sulfanyl‐1H‐isoindol‐1‐ones 1 via Pummerer‐type cyclization of N‐aryl‐2‐(sulfinylmethyl)benzamides 2 is described. Thus, treatment of these sulfinyl‐benzamides 2 , easily prepared from 2‐(bromomethyl)benzoates 3 in three steps, with Ac2O at ca. 100° resulted in the formation of the desired isoindolones 1 in generally good yields. 相似文献
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2‐(1‐Aryl‐2‐methoxyethenyl)benzaldehydes 2 , obtained by successive treatment of 1‐(1‐aryl‐2‐methoxyethenyl)‐2‐bromobenzenes 1 with BuLi and 1‐formylpiperidine, were transformed to the corresponding phenylhydrazones 3 on treatment with PhNHNH2. When these hydrazones were allowed to react with conc. HBr, cyclization, followed by dehydrogenation with air occurred, furnished 3‐aryl‐2‐methoxyinden‐1‐one (Z)‐phenylhydrazones 4 . 相似文献
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In the presence of titanium(IV) tetraethoxide ((EtO)4Ti), menthyl arylglyoxylates are prepared by transesterification of ethyl arylglyoxylates and natural (−)‐(1R,2S,5R)‐menthol. Using menthyl as a chiral auxiliary, the corresponding novel (R)‐menthyl 2‐aryl‐2‐hydroxybutanoates are synthesized by the addition of Et2Zn with menthyl arylglyoxylates. The structures of the products are characterized by IR and 1H‐ and 13C‐NMR spectroscopy, mass spectrometry, and elemental analysis. The diastereoselectivities are analyzed by HPLC. The addition reactions are completed with good yields and high diastereoisomeric excess (de up to 95%), and, after hydrolysis, the (R)‐2‐aryl‐2‐hydroxybutanoic acids are obtained with high optical purities. 相似文献
4.
Chemoselective Route for Synthesis of N‐Aryl‐3‐oxochromeno[2,3‐c]pyrazole‐2(3H)‐carbothioamide Derivatives 下载免费PDF全文
A chemoselective route for the synthesis of chromeno[2,3‐c]pyrazole‐2(3H)‐carbothioamide derivatives by a five‐component reaction of salicylaldehyde, malononitrile, NH2NH2?H2O, aryl isothiocyanate, and H2O in EtOH/AcOH mixture is reported. This new protocol has the advantages of high yields, short reaction times, ease of operation, and simple purification. All structures were confirmed by IR, 1H‐ and 13C‐NMR, and MS analyses. A plausible mechanism for this type of reaction is proposed (Scheme 2). 相似文献
5.
The base catalyzed intramolecular nucleophilic cyclization of 1‐(2‐haloaroyl)‐3‐aryl thioureas ( 1a‐i ), in the presence of DMF afforded the 1‐aryl‐2‐thioxo‐2,3‐dihydro‐1H‐quinazolin‐4‐ones ( 2a‐i ). The structures were confirmed by spectroscopic data, elemental analyses and in case of the 2c by single crystal X‐ray diffraction data. The mechanistic studies support an intramolecular nucleophilic substitution (SNAr mechanism) rather than intramolecular aromatic substitution (SRN1 mechanism). 相似文献
6.
Kazuhiro Kobayashi Natsuki Konishi Teruhiko Suzuki Kazuhiro Nakagawa 《Helvetica chimica acta》2013,96(8):1452-1456
An efficient one‐pot synthesis of novel heterocyclic derivatives, 2‐aryl‐1,4‐oxathiino[2,3‐b]quinoxalines or ‐pyrazines 5 , via the reaction of 2,3‐dichloroquinoxaline or ‐pyrazine with Na2S?9 H2O, and subsequent treatment of the resulting 2‐chloro‐3‐sodiosulfanylquinoxaline or ‐pyrazine 2 with 1‐aryl‐2‐bromo‐1‐alkanones and then NaH under mild conditions is described. 相似文献
7.
Electron impact-induced fragmentation mechanism of Trans-α-Aryl-β-enamino esters were investigated using mass-analyzed ion kinetic energy (MIKE) spectrometry and high resolution accurate mass data It was found that the main characteristic fragmentations of compounds studied were:an odd electron ion M^ -EtOH was formed by losing a neutral molecule of ethanol;and the skeletal rearrangements took place;and the ring opening reaction happened after losing a carbon monoxide;and the typical McLafferty rearrangement underwent in ester group.The cycliztion reation caused by losing neutral molecule of TsNH2 due to the ortho-effects of substituted group of gromatic ring was also observed. 相似文献
8.
Kazuhiro Kobayashi Kota Matsumoto Daizo Nakamura Shuhei Fukamachi Hisatoshi Konishi 《Helvetica chimica acta》2010,93(6):1048-1051
A facile method for the synthesis of 2,3‐dihydro‐3‐methylidene‐1H‐isoindol‐1‐one and its derivatives carrying substituent(s) at C(5) and/or C(6) has been developed. The reaction of 2‐formylbenzonitrile ( 1a ) with dimethyloxosulfonium methylide, generated by the treatment of trimethylsulfoxonium iodide with NaH in DMSO/THF at 0°, resulted in the formation of 2,3‐dihydro‐3‐methylidene‐1H‐isoindol‐1‐one ( 2a ) in 77% yield. Similarly, six 2‐formylbenzonitriles carrying substituent(s) at C(4) and/or C(5), i.e., 1b – 1g , also gave the corresponding expected products 2b – 2g in comparable yields. 相似文献
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HClO4‐SiO2, efficiently catalyzed the condensation of o‐aminophenols and 2‐bromo‐1‐aryl‐ethanones to yield 3‐aryl‐2H‐benzo[1,4]oxazines in good yields. 相似文献
12.
4‐Arylisocoumarins (=4‐aryl‐1H‐2‐benzopyran‐1‐ones) 6 were prepared from 2‐(1‐aryl‐2‐methoxyethenyl)‐1‐bromobenzenes 1 . Successive treatment of these bromo styrenes with BuLi and 1‐formylpiperidine gave a mixture of (E)‐ and (Z)‐2‐(1‐aryl‐2‐methoxyethenyl)benzaldehydes 2 . Hydrolysis of (Z)‐isomers with conc. HBr, followed by pyridinium chlorochromate (PCC) oxidation of the resulting 1H‐2‐benzopyran‐1‐ol derivatives 4 (and 5 ), afforded the desired products. 相似文献
13.
Eight mono-reactive and four bis-reactive 2,3-epoxy/3-chloro-2-hydroxy propyl derivatives of quaternary ammonium salts have been synthesised by reacting epichlorohydrin with suitable tertiary amines and diamines. Mono-reactive derivatives also contain cyano and carboxylic groups in addition to 2,3-epoxy/3-chloro-2-hydroxy propyl groups. The structures of these quaternary ammonium salts have been characterised using IR and 1H NMR spectroscopic techniques. These quaternary ammonium chlorides have been applied to the cotton fabrics as pretreatments and aftertreatments and promising results have been obtained. 相似文献
14.
A series of N‐aryl 2‐alkenamides were produced efficiently by treating N‐aryl 3‐(phenylsulfonyl)‐propanamides with potassium tert‐butoxide in THF at 0°C. With out isolation, it was further treated with an additional equivalent of potassium tert‐butoxide and allyl bromide to give N‐allyl N‐aryl 2‐alkenamides in one pot in good yields. Followed by a ring‐closing metathesis reaction, these N‐allyl N‐aryl 2‐alkenamides were respectively converted into corresponding N‐aryl α,β‐unsaturated γ‐lactams in moderate yields. 相似文献
15.
The polystyrene‐supported α‐selenoacetic acid and α‐selenopropionic acid were prepared and used for the synthesis of 2‐alkenamides from primary and secondary amines in good yields and high purities. 相似文献
16.
Pedro Álvarez‐Boo José S. Casas Eduardo E. Castellano M. Delfina Couce Rosa Farto Eduardo Freijanes José Sordo 《应用有机金属化学》2007,21(1):49-53
Reaction of 3‐(2‐methoxyphenyl)‐2‐sulfanylpropenoic acid [H2(o‐mpspa)] with SnPh3OH in the presence of di‐isopropylamine resulted in the formation of the complex [HQ][SnPh3(o‐mpspa)] (where HQ = di‐isopropylammonium cation and o‐mpspa = 3‐(2‐methoxyphenyl)‐2‐sulfanylpropenoato), which was characterized by mass spectrometry and vibrational spectroscopy, as well as by 1H, 13C and 119Sn NMR spectroscopy. The single‐crystal X‐ray structural analysis of the new complex shows a trigonal‐bipyramidal coordination geometry around the Sn atom where o‐mpspa behaves as a bidentate chelating ligand. Dimeric units arise from the existence of N? H…O hydrogen bonds between the NH2 group of the di‐isopropylammonium cation and the oxygen atoms of the two neighbouring carboxylato groups. The bacteriostatic activity of the complex is also reported. Copyright © 2007 John Wiley & Sons, Ltd. 相似文献
17.
Kazuhiro Kobayashi Taketoshi Kozuki Manami Konishi Teruhiko Suzuki Miyuki Tanmatsu Hisatoshi Konishi 《Helvetica chimica acta》2011,94(7):1234-1238
The reaction of aryl(3‐isocyanopyridin‐4‐yl)methanones 1 , easily prepared from commercially available pyridin‐3‐amine, with aryl Grignard reagents gave, after aqueous workup, 2,3‐diaryl‐3H‐pyrrolo[2,3‐c]pyridin‐3‐ols 2 . These rather unstable alcohols were O‐acylated with Ac2O in pyridine in the presence of a catalytic amount of 4‐(dimethylamino)pyridine (DMAP) to afford the corresponding 2,3‐diaryl‐3H‐pyrrolo[2,3‐c]pyridin‐3‐yl acetates 3 in relatively good yields. 相似文献
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Yuuya Ookubo Prof. Dr. Atsushi Wakamiya Prof. Dr. Hideki Yorimitsu Prof. Dr. Atsuhiro Osuka 《Chemistry (Weinheim an der Bergstrasse, Germany)》2012,18(40):12690-12697
A library of 2‐aryl‐3‐trifluoromethylnaphthofurans was synthesized with high efficiency from simple naphthols. In this synthesis, the Pummerer‐type annulation of naphthols with 3‐(2,2,2‐trifluoroethylidene)‐2,4‐dithiapentane 2‐oxide was followed by a cross‐coupling of the resulting 2‐methylthio‐3‐trifluoromethylnaphthofurans with a variety of arylzinc reagents. A palladium complex, Pd‐PEPPSI‐IPr, was the most efficient catalyst for the arylation step, which represents the first cross‐coupling of aryl sulfides by using an N‐heterocyclic‐carbene‐ligated palladium complex. This library consists of new π‐expanded molecules, all of which are fluorescent in the solid state as well as in solution. Their photophysical properties, such as absorption and emission, fluorescence quantum yields, and fluorescence lifetimes, were thoroughly investigated. This library was also useful to identify acidochromic molecules. 相似文献
20.
Rekha S. Hunoor Basavaraj R. Patil Dayananda S. Badiger Ramesh S. Vadavi Kalagouda B. Gudasi V. M. Chandrashekhar I. S. Muchchandi 《应用有机金属化学》2011,25(6):476-483
A new quinazolinone derivative, 3‐[1‐(2‐hydroxyphenyl)ethylideamino]‐2‐phenyl‐3,4‐dihydroquinazolin‐4(3H)‐one ( LH ) was synthesized by the condensation of 2‐hydroxyacetophenone‐2‐aminobenzoylhydrazone and benzaldehyde. The cyclization to form 1,2‐dihydroquinazolinone was confirmed by IR, 1D and 2D HETCOR studies. Coordination compounds of Co(II), Ni(II), Cu(II) and Zn(II) of LH were synthesized and characterized using various physico‐chemical studies like stoichiometric, conductivity, magnetic moment measurements and spectral techniques such as IR, NMR, UV‐vis and EPR spectroscopy. The elemental analysis and thermal studies suggested a general stoichiometry [M(HEPDQ)Cl] for all the complexes. A four‐coordinate geometry was assigned to all the complexes. The complexes along with the parent ligand were screened for their anti‐inflammatory activity, using carrageenan‐induced rat paw edema, and for their analgesic activity by Eddy's hot plate method. The activity of the ligand was enhanced on complexation with metal ions. This enhanced activity was attributed to the increased lipophilic nature of the complexes. Notable anti‐inflammatory activity was observed for Ni(II), Cu(II) and Zn(II) complexes. The analgesic activity of the ligand was greater than the standard at 60 min. and at a 10 mg kg−1 dose, whereas the activity of Ni(II) and Cu(II) complexes at 10 mg kg−1 dose was comparable with the standard used. Copyright © 2011 John Wiley & Sons, Ltd. 相似文献