岡田 悦治 | ![]() |
オカダ エツジ | |
大学院工学研究科 応用化学専攻 | |
准教授 | |
化学関係 |
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研究論文(学術雑誌)
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研究論文(学術雑誌)
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Aromatic nucleophilic substitution reaction of N,N-dimethyl-2-methoxy-3-trifluoroacetyl-4-quinolylamine with various nucleophiles (NuH) such as amines, thiols, and alcohols proceeded chemoselectively at the 4-position to give the corresponding Me2N-Nu exchanged products. Novel fluorine-containing 6-methoxydibenzo[b,h][1,6]naphthyridines (11) and 6-methoxythiochromeno[3,2-c]quinolines (12) were synthesized in moderate to high yields by the trifluoromethanesulfonic acid catalyzed cyclization of thus obtained N-aryl-2-methoxy-3-trifluoroacetyl-4-quinolylamines (8) and aryl 2-methoxy-3-trifluoroacetyl-4-quinolyl sulfides (9), respectively.
PERGAMON-ELSEVIER SCIENCE LTD, 2017年01月, HETEROCYCLES, 95 (1), 322 - 341, 英語[査読有り]
研究論文(学術雑誌)
2-Methoxy-3-trifluoroacetyl-4-quinolylamine reacted easily with various aldehydes in the presence of aqueous ammonia to afford mainly trifluoromethylated pyrimido[5,4-c]quinoline derivatives in moderate to high yields. In contrast, the use of ketones instead of aldehydes in the presence of pyrrolidine, exclusively gave benzo[h][1,6]naphthyridine derivatives in good to excellent yields.
PERGAMON-ELSEVIER SCIENCE LTD, 2017年, HETEROCYCLES, 94 (1), 102 - 116, 英語[査読有り]
研究論文(学術雑誌)
N,N-Dimethy1-2-methoxy-3-trifluoroacety1-4-quinolylamine underwent chemoselective aromatic nucleophilic N-N exchange reaction with hydrazines followed by cyclocondensation to afford the corresponding novel fluorine-containing 4-methoxy-1H-and 2H-pyrazolo[4,3-c]quinolines in good to high yields. Furthermore, the use of 1,2-ethylenediamine and 1,2-phenylenediamines gave the corresponding fluorine-containing 6-methoxy-1,4-diazepino[6,5-c]quinoline derivatives in good yields.
PERGAMON-ELSEVIER SCIENCE LTD, 2016年05月, HETEROCYCLES, 92 (5), 936 - 943, 英語[査読有り]
研究論文(学術雑誌)
Aromatic nucleophilic substitution reaction of 4-dimethylamino-2-methoxy-3-trifluoroacetylquinoline with various nucleophiles (NuH) such as amines, thiols, and alcohols proceeded chemoselectively to give the corresponding Me2N-Nu exchanged products, 2-methoxy-3-trifluoroacetyl-4-quinolylamines, sulfides, and ethers without any formation of MeO-Nu exchanged products in spite of the common knowledge that alkoxy group is the better leaving group than amino group.
PERGAMON-ELSEVIER SCIENCE LTD, 2016年04月, HETEROCYCLES, 93 (2), 474 - 481, 英語[査読有り]
研究論文(学術雑誌)
1,5-Sigmatropic hydrogen shifts on two types of azadiene systems, O-protonated beta-trifluoroacetylenamines 9 and 3,3,3-trifluoro-1-alkylideneaminopropen-2-ols 10, are elucidated on the basis of DFT calculations to develop new synthetic methodologies accessing novel fluorine-containing heterocycles. These results suggest that the 1,5-hydrogen shift on 9 and 10 requires slightly further enhanced conditions compared with the corresponding step on diazadiene systems, O-protonated 1,1,1-trifluoro-3-hydrazono-2-alkanones 3, which results in the derivation of oxadiazines 2.
PERGAMON-ELSEVIER SCIENCE LTD, 2016年04月, HETEROCYCLES, 93 (1), 243 - 249, 英語[査読有り]
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3-Trifluoroacetylquinolin-4-amine reacted easily with various aldehydes in the presence of aqueous ammonia to afford mainly trifluoromethylated pyrimido[5,4-c]quinoline derivatives in moderate to high yields. In contrast, the use of ketones instead of aldehydes under almost the same conditions, mostly gave benzo[h][1,6]naphthyridine derivatives in excellent combined yields.
PERGAMON-ELSEVIER SCIENCE LTD, 2014年10月, HETEROCYCLES, 89 (10), 2303 - 2317, 英語[査読有り]
研究論文(学術雑誌)
Novel fluorine-containing dibenzo[b,h][1,6]naphthyridines (3), thiochromeno[3,2-c]quinolines (5), and chromeno[3,2-c]quinolines (7) were synthesized in moderate to high yields by the trifluoromethanesulfonic acid catalyzed cyclization of N-aryl-3-trifluoroacetyl-4-quinolylamines (2) and aryl 3-trifluoroacetyl-4-quinolyl sulfides (4) and ethers (6), easily prepared by aromatic nucleophilic substitution reactions of N,N-dimethyl-3-trifluoroacetyl-4-quinolylamine (1) with p-substituted anilines, thiophenols, and phenols, respectively.
PERGAMON-ELSEVIER SCIENCE LTD, 2014年01月, HETEROCYCLES, 88 (1), 799 - 806, 英語[査読有り]
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In this paper we report the synthesis and antimalarial properties of two series of fluoroalkylated γ-lactams derived from 4-aminoquinoline as potent chemotherapeutic agents for malaria treatment. These molecules obtained in several steps resulted in the identification of very potent structures with in vitro activity against Plasmodium falciparum clones of variable sensitivity(3
American Chemical Society, 2013年01月, J. Med. Chem., 56 (1), 73 - 83, 英語[査読有り]
研究論文(学術雑誌)
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New 6,8-bis(trifluoroacetyl)quinolin-5-amines (6) were easily prepared in moderate to high yields by the aromatic nucleophilic nitrogen-nitrogen exchange reaction of N,N-dimethyl-6,8-bis(trifluoroacetyl)-quinolin-5-amine (5) with various aliphatic and aromatic amines.
PERGAMON-ELSEVIER SCIENCE LTD, 2012年01月, HETEROCYCLES, 84 (2), 1277 - 1284, 英語[査読有り]
研究論文(学術雑誌)
New 3-trifluoroacetyl-4-quinolylamines (2), sulfides (3), and ethers (4) were synthesized in good to high yields by aromatic nucleophilic substitution reactions of N,N-dimethyl-3-trifluoroacetyl-4-quinolylamine (1), which was easily prepared by acylation of N,N-dimethyl-4-quinolylamine with 1-trifluoroacetyl-4-dimethylaminopyridinium trifluoroacetate, with amines, thiols, alcohols, and phenols. © 2012 The Japan Institute of Heterocyclic Chemistry.
The Japan Institute of Heterocyclic Chemistry, 2012年, Heterocycles, 86 (2), 1177 - 1185, 英語[査読有り]
研究論文(学術雑誌)
2,4-Diethoxy-6-trifluoromethyl-3,4-dihydro-2H-pyran was reacted with thiols in the presence of p-toluenesulfonic acid by heating followed by treatment with trifluoroacetic acid to afford the corresponding 4-trifluoroacetyl-1,3- butadienyl sulfides selectively. Our DFT calculation results suggest thermodynamically controlled attack of thiols at 6-position of pyrylium intermediate followed by electrocyclic ring-opening as a reasonable mechanism for this reaction. © 2012 The Japan Institute of Heterocyclic Chemistry.
The Japan Institute of Heterocyclic Chemistry, 2012年, Heterocycles, 86 (1), 705 - 712, 英語[査読有り]
研究論文(学術雑誌)
6,8-Bis(trifluoroacetyl)quinolin-5-amine reacted easily with various aldehydes in the presence of aqueous ammonia to afford trifluoromethylated pyrido[2,3-h]quinazoline derivatives and 1,7-phenanthroline derivatives in good to excellent yields. Under almost the same conditions, the use of ketones instead of aldehydes gave 1,7-phenanthroline derivatives selectively, except in the case of cyclohexanone.
GEORG THIEME VERLAG KG, 2011年09月, SYNTHESIS-STUTTGART, No.17・pp.2754 (17), 2754 - 2760, 英語[査読有り]
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The reaction of N-propargyl-6,8-bis(trifluoroacetyl)quinolin-5-amine (1) with various active methylene compounds gave the novel fluorine-containing 1,7-phenanthroline derivatives (3). Furthermore, changing the electron-withdrawing groups on active methylene compounds induced interesting alternation of the reaction site wherein the enolate anions attack first and led to construction of the different nitrogen-containing heterocyclic systems, 1,7-phenanthrolinone (4) and 1,4-dihydro-1,7-phenanthroline (5).
PERGAMON-ELSEVIER SCIENCE LTD, 2010年12月, HETEROCYCLES, 82 (1), 803 - 812, 英語[査読有り]
研究論文(学術雑誌)
N-Propargyl-2,4-bis(trifluoroacetyl)-l-naphthylamine (3) underwent nitrogen-containing heterocyclic ring-formation reactions with a variety of active methylene compounds in the presence of sodium alkoxides. This annulation reactions with dialkyl malonates were highly dependent on reaction temperature to give selectively the corresponding fluorine-containing benzo[h]quinolines (5) at high temperature and IH-benzo[h]quinolin-2-ones (7 and 8) at low temperature. Furthermore, changing the electron-withdrawing groups of active methylene compounds led to alternation of the reactive site wherein the reagents attack first and to the formation of the different nitrogen-containing heterocyclic systems, pyridine (9), dihydropyridine (11 and 13) and pyridone (12).
PERGAMON-ELSEVIER SCIENCE LTD, 2010年02月, HETEROCYCLES, 81 (2), 357 - 370, 英語[査読有り]
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Novel fluorine-containing 1,7-phenanthrolines with a variety of substituents at the 3-position were easily synthesized in moderate to high yields by the pyridine-ring formation reaction of' N-propargyl-6,8-bis(trifluoroacetyl)quinolin-5-amine with various amines, thiols, alcohols, and phenols.
GEORG THIEME VERLAG KG, 2009年09月, SYNTHESIS-STUTTGART, -・-・3039 (18), 3039 - 3046, 英語[査読有り]
研究論文(学術雑誌)
Novel fluorine-containing 1,10-phenanthrolines having a variety of substituents at the 3-position were easily synthesized in moderate yields by the pyridine-ring formation reaction of N-propargyl-5,7-bis(trifluoroacetyl)-8-quinolylamine with various amines, thiols, and phenols. Unexpectedly. the reactive intermediates 1,4-dihydro-1,10-phenanthrolin-4-ols were isolated for the first time in the reactions with dialkylamines. (C) 2009 Elsevier Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, 2009年08月, TETRAHEDRON, 65 (31), 6189 - 6195, 英語[査読有り]
研究論文(学術雑誌)
N-Propargyl-2,4-bis(trifluoroacetyl)-1-naphthylamine (3) underwent nitrogen-containing heterocyclic ring-formation reactions with active methylene compounds such as dialkyl malonates in the presence of sodium alkoxides. This ring closure reactions were very dependent on reaction temperature to give selectively the corresponding fluorine-containing benzo[h]quinolines (5) at high temperature and 1H-benzo[h]quinolin-2-ones (7 and 8) at low temperature.
PERGAMON-ELSEVIER SCIENCE LTD, 2009年04月, HETEROCYCLES, 79, 395 - 401, 英語[査読有り]
研究論文(学術雑誌)
beta-Trifluoroacetylketene dialkyl acetals (3 and 5) reacted easily with various 1,2-phenylenediamines to give novel 4-alkoxy-2-trifluoromethyl-2,3-dihydro-1H-benzo[b][1,4]diazepinols (6 and 8) in moderate to high yields. Dehydration of 6 and 8 proceeded thermally under reduced pressure to afford the corresponding fluorine-containing 3H-benzo[b][1,4]diazepines (7 and 9).
PERGAMON-ELSEVIER SCIENCE LTD, 2009年02月, Heterocycles, 77 (2), 983 - 990, 英語[査読有り]
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Novel fluorine-containing 1,10-phenanthrolines having dialkyl-, alkyl, and arylaminomethyl substituents at the 3-position were easily synthesized in moderate yields by the pyridine-ring formation reaction of N-propargyl-5,7-bis(trifluoroacetyl)-8-quinolylamine with various a mines. Unexpectedly, the reactive intermediates 1,4-dihydro-1,10-phenanthrolin-4-ols were isolated for the first time in the reactions with dialkylamines. (C) 2008 Elsevier Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, 2008年12月, TETRAHEDRON LETTERS, 49 (50), 7161 - 7164, 英語[査読有り]
研究論文(学術雑誌)
The reactions of 1,1,1,5,5,5-hexafluoro-3-(isobutoxymethylene)-pentane-2,4-dione (1) with various benzene-1,2-diamines gave 2,5-dihydro-3-trifluoroacetyl-2-trifluoromethyl-1H-benzo[b][1,4]diazepines (5) in moderate to high yields under very mild conditions. Also, 2,5-dihydro-3-perhaloalkanoyl-2-perhaloalkyl-1H-benzo[b][1,4]diazepines (7) were synthesized successfully by quite similar manner. Reactions of thus obtained dihydrobenzo[b][1,4]-diazepinols (5) with thionyl chloride gave unexpected novel fluorine-containing N-sulfinylanilines (9).
PERGAMON-ELSEVIER SCIENCE LTD, 2008年11月, HETEROCYCLES, 76 (2), 1205 - 1217, 英語[査読有り]
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New 1,1,1,5,5,5-hexafluoro-3-[(E)-3-arylallylidene]pentane-2,4-diones were synthesized in moderate to high yields by the ring-opening reaction of 1-(2-ethoxy-4-isobutoxy-6-trifluoromethyl-3,4-dihydro-2H-pyran-5-yl)-2,2,2-trifluoroethanone with aromatic compounds in refluxing trifluoroacetic acid.
PERGAMON-ELSEVIER SCIENCE LTD, 2008年09月, HETEROCYCLES, 76 (1), 215 - 219, 英語[査読有り]
研究論文(学術雑誌)
The synthesis of N-(2-trifluoroacetylaryl)propargylamines 10-14 and 17 is presented. The copper(I) catalyzed cycloaddition reaction of these propargylamines (dipolarophiles) with a series of azides (1,3-dipoles) 18-20, 21 and 24 was found to proceed smoothly in dimethylsulfoxide at room temperature, to furnish the corresponding 1,4-disubstituted-[1,2,3]triazole derivatives 26-36 in moderate to good yields. (c) 2008 Elsevier B.V. All rights reserved.
ELSEVIER SCIENCE SA, 2008年09月, JOURNAL OF FLUORINE CHEMISTRY, 129 (9), 788 - 798, 英語[査読有り]
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New fluorinated 4H-benzo[h]chromen-4-one and 4H-pyrano[3,2-h]quinolin-4-one derivatives are obtained in moderate to good yields, through a one-pot aldolization-intramolecular SNAr process, from the tetrakis(dimethylamino)ethylene (TDAE) mediated reductive cleavage of two N,N-dimethylamino-bis-chlorodifluoroacetyl substrates in the presence of heteroaryl aldehydes. (c) 2007 Elsevier Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, 2008年01月, TETRAHEDRON LETTERS, 49 (4), 589 - 593, 英語[査読有り]
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Thermal reaction of 5-aryl-6-trifluoromethyl-3,6-dihydro-2H[1,3,4]oxadiazines (2) readily obtainable from 3-aryl-3-dimethylhydrazono-1,1,1-trifluoro-2-propanones (1) afforded 4-aryl-1-methyl-5-trifluoromethylimidazoles (3) in moderate to good yields. Mechanism for this thermal transformation reaction is also discussed.
PERGAMON-ELSEVIER SCIENCE LTD, 2007年, HETEROCYCLES, 74, 351 - 356, 英語[査読有り]
研究論文(学術雑誌)
2,3-Dimethylthiazolium iodides (1) reacted easily with trifluoroacetic anhydride in the presence of pyridine to give 2-bis(trifluoroacetyl)methylene-2,3-dihydro-3-methylthiazoles (2) in excellent yields. Deacylation of 2 proceeded readily in moderate to high yields by acid catalyst such as silica gel and aqueous hydrochloric acid to afford the corresponding 2-trifluoroacetylmethylene-2,3-dihydro-3-methylthiazoles (3), which were smoothly reconverted into diacylated compounds (2) with trifluoroacetic anhydride. The highly poralized structure of 2 was also briefly discussed.
PERGAMON-ELSEVIER SCIENCE LTD, 2007年, HETEROCYCLES, 74, 721 - 730, 英語[査読有り]
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We succeeded in the synthesis of N,N-dimethyl-2-trifluoroacetyl-l-naphthylamine (10) by the regioselective deacylation of N,N-dimethyl-2,4-bis(trifluoroacetyl)-1-naphthylamine with trifluoroacetic acid and water. The aromatic nucleophilic substitutions of 10 with various amines, thiols and alcohols proceeded cleanly to give the corresponding N-N, N-S and N-O exchanged products in moderate to excellent yields. (C) 2003 Elsevier Science Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, 2003年01月, TETRAHEDRON LETTERS, 44 (4), 741 - 744, 英語研究論文(学術雑誌)
Acylation of 4-dimethylaminoquinoline with 1-trifluoroacetyl-4-dimethylaminopyridinium trifluoroacetate proceeded cleanly to give 3-trifluoroacetyl-4-dimethylaminoquinoline which underwent nucleophilic aromatic substitutions with various amines to afford the corresponding N-N exchanged 3-trifluoroacetyl-4-aminoquinolines in excellent yields.
CHEMICAL SOC JAPAN, 2000年01月, CHEMISTRY LETTERS, (1), 50 - 51, 英語[査読有り]
研究論文(学術雑誌)
Acid-catalyzed cyclization of N-aryl-5,7-bis(trifluoroacetyl)-8-quinolylamines (2), prepared by aromatic nucleophilic nitrogen-nitrogen exchange reaction of N,N-dimethyl-5,7-bis(trifluoroacetyl)-8-quinolylamine (1) with p-substituted anilines, afforded fluorine-containing benzo[b][1,10] phenanthrolines (3) in excellent yields.
PERGAMON-ELSEVIER SCIENCE LTD, 1999年11月, HETEROCYCLES, 51 (11), 2697 - 2702, 英語[査読有り]
研究論文(学術雑誌)
Nucleophilic substitutions at olefinic carbon atoms of 4-trifluoroacetyl- and 4,4-bis(trifluoroacetyl)-1,3-butadienyl sulfides and -amines with various amines proceed easily under mild conditions to give the corresponding S-N and N-N exchanged products.
The Chemical Society of Japan, 1990年, Chemistry Letters, (11), 2095 - 2098, 英語その他
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