• Title/Summary/Keyword: [5+2] Cycloaddition reaction

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AgBF4/[Bmim]BF4-Catalyzed [3+2] Cycloaddition of Cyclic Diazodicarbonyl Compounds: Efficient Synthesis of 2,3-Dihydrofurans and Conversion to 3-Acylfurans

  • Xia, Likai;Lee, Yong-Rok;Kim, Sung-Hong;Lyoo, Won-Seok
    • Bulletin of the Korean Chemical Society
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    • v.32 no.5
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    • pp.1554-1558
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    • 2011
  • A novel and efficient method for the synthesis of 2,3-dihydrofurans bearing a variety of substituents on the dihydrofuran ring was achieved by the reaction of cyclic diazodicarbonyl compounds with styrene and vinyl acetate. The key strategy was AgBF$_4$/[Bmim]BF$_4$-catalyzed [3+2] cycloaddition. The synthesized dihydrofurans with an acetate group were further converted to the corresponding 3-acylfurans.

Heterocyclization Reaction of 4-(2-Methylaziridin-1-yl)-3-ureidobenzotrifluorides under Appel's Conditions

  • Cho, Hyun-In;Lee, Kee-Jung
    • Bulletin of the Korean Chemical Society
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    • v.24 no.2
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    • pp.189-192
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    • 2003
  • The reaction of 4-(2-methylaziridin-1-yl)-3-ureidobenzotrifluorides 4 with triphenylphosphine, carbon tetrachloride, and triethylamine (Appel's condition) led to the corresponding carbodiimides 5, which underwent intramolecular cycloaddition reaction with aziridine under the reaction condition to give the benzimidazolefused heterocycles, 2,3-dihydro-1H-imidazo[1,2-a]benzimidazoles 8 and 12,13-dihydro-5H-benzimidazo[2,3-b] [1,3]benzodiazepines 9.

Microwave Assisted Reaction of Condensed Thiophenes With Electron Poor Olefins

  • Al-zaydi, Khadijah M.;Elnagdi , Mohamed H.
    • Journal of the Korean Chemical Society
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    • v.47 no.6
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    • pp.591-596
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    • 2003
  • Aminothienopyridazines 1a, b and aminothienocoumarin 2 condensed with DMFDMA to yield amidines 3a, b and 4. These compounds reacted with N-phenylmaleimide to yield 9 and 10. On the other hand reacting 3a, b, 4, 18, 19 and 20 with maleic anhydride afforded only the formylated derivatives 5a, b, 6, 21, 22 and 23 respectively. The reaction of 3a, b with diethyl fumarate afforded 11, formed most likely via hydrolysis of the amidine 14 during working up the reaction mixture. Irradiation of N-phenylmaleimide in microwave oven afforded [2+2] and [2+2+2] cycloaddition product.

Synthesis of Polymers Including Both Triazole and Tetrazole by Click Reaction

  • Shin, Jung-Ah;Lim, Yeong-Gweon;Lee, Kyung-Hee
    • Bulletin of the Korean Chemical Society
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    • v.32 no.2
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    • pp.547-552
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    • 2011
  • Azido contained polymers were treated with various substituted N-propargyl tetrazoles in $CH_2Cl_2/H_2O$ at room temperature by Cu-catalyzed [2+3] cycloaddition to afford high yields of the corresponding polymers, possessing both triazole and tetrazole moiety.

A Model Study toward the Synthesis of Xestoquinone (Xestoquinone의 합성에 대한 모델연구)

  • Ahn Chan Mug;Ho Bum Woo
    • Journal of the Korean Chemical Society
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    • v.47 no.4
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    • pp.354-362
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    • 2003
  • A strategy for synthesis of the furan-fused tetracyclic system of xestoquinone was explored through a model study. Using 3-butyn-1-ol as a starting material, 5-iodo-1-methoxymethoxy pentyne (5) was prepared in 5 steps. Reaction of ethyl 2-phenylpropanoate with 5 gave ethyl 7-methoxymethoxy-2-methyl-2-phenyl-5-heptynoate (6) in 88% yield, and then methyl 9-oxo-4-methyl-4-phenyl-2,7-nonadiynoate (13), the key intermediate, was synthesized in 6 steps from the ester 6. Intramolecular cycloaddition reaction of 13 afforded isobenzofuran 14 in 5% yield, which was converted to the tetracyclic structure 15 in the presence of Lewis acid.

Novel Synthesis of the Natural Protoberberine Alkaloids: Oxypalmatine and Oxypseudopalmatine

  • Le, Thanh Nguyen;Cho, Won-Jea
    • Bulletin of the Korean Chemical Society
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    • v.28 no.5
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    • pp.763-766
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    • 2007
  • Oxypalmatine and oxypseudopalmatine were synthesized in three steps from the benzonitrile 11 and toluamides 12a, b. The lithiated cycloaddition reaction yielded 3-arylisoquinolinone intermediates. A subsequent internal SN2 reaction produced the corresponding 8-oxoprotoberberines, oxypalmatine and oxypseudopalmatine.

Synthesis and Cycloaddition Reaction of C-(2-naphthoyl)-N-arylmethanohydrazonoylpyridinium Bromides

  • Hassaneen, Hamdi M.;Shawali, Ahmad S.;Elwan, Nehal M.;Abounada, Nada M.;Algharib, Mohammed S.
    • Archives of Pharmacal Research
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    • v.15 no.4
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    • pp.292-297
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    • 1992
  • Coupling of naphthacylpyridinium bromide 2 [1-(2-naphthyl) ethanone-2-pyridinium bromide] with N-nitrosoacetarylamides afforded C-(2-naphthoyl)-N-arylmethanohydrazonoylpyridinium bromides 3A-C. Treatment of 3A-C with base afforded the corresponding tetrazines 6A-C. Cycloaddition of nitrilimines 5A-C to N-arylmaleimides, acrylonitrile, ethyl acrylate, acrylamide, fumaronitrile, $\alpha$-cyanocinnamonitriles, ethyl $\alpha$-cyano-p-nitrocinnamates and $\alpha$-cyano-p-nitrocinnamamide afforded the corresponding cycloadducts 7-14, respectively. The cycloadducts 11-14 undergo a facile thermal elimination of hydrogen cyanide to give the corresponding pyrazoles 18-21 respectively.

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New Synthesis of Perhydrotriazolotriazoles Catalyzed by TiCl4 under Ambient Conditions

  • Safari, J.;Gandomi-Ravandi, S.;Ghotbinejad, M.
    • Journal of the Korean Chemical Society
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    • v.56 no.1
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    • pp.78-81
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    • 2012
  • Aromatic 2,3-diazabuta-1,3-dienes in glacial acetic acid with isothiocyanate in the presence of catalyst $TiCl_4$ at room temperature produced via criss-cross cycloaddition reactions the corresponding perhydro[1,2,4]triazolo[1,2-a][1,2,4] triazole-1,5-dithiones in relatively high yields and short reaction time.