- A concise new synthesis of angular furanocoumarins: Angelicin, oroselone and oroselol
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An efficient synthesis of angular furanocoumarins has been carried out starting from dihydrobenzofuran derivatives.
- Lee
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- CYCLIZATIONS OF SOME FURYL ACID CHLORIDES
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Intramolecular Friedel-Crafts acylation of the furan ring has been accomplished in good yields with stannic chloride for both furyl isomers of butyryl acid chloride.The propionyl chloride isomers, however, failed to produce reasonable quantities of the cyclic ketone.
- Walsh, Edward J.,Stone, Guy B.
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- ANTIMICROBIAL AGENTS AND COMPOSITIONS AND USES THEREOF
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Described herein are compounds that act as antimicrobial agents, compositions comprising these compounds, and methods of their use in to treating infections caused by Helicobacter pylori (H. pylori) or killing or inhibititing the growth of H. pylori.
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Paragraph 0252-0253
(2021/04/01)
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- Preparation method of polysubstituted furan compound
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The invention discloses a preparation method of a polysubstituted furan compound, which comprises the following steps: by using a carbonyl compound with an electron withdrawing group at the alpha position and dichloroolefin as raw materials, reacting under alkaline conditions to obtain a 2, 3-disubstituted furan compound and a 2, 3, 5-trisubstituted furan compound. The method has the advantages ofno need of transition metal catalysis, strong substrate applicability, cheap and easily available raw materials, simple operation, high efficiency and wide application prospect.
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Paragraph 0003
(2021/02/10)
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- CXCR2 ANTAGONIST
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A compound as a CXCR2 antagonist and an application thereof in preparing a drug as a CXCR2 antagonist. In particular, the present invention relates to a compound represented by formula (II) or an isomer or pharmaceutically acceptable salt thereof.
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Paragraph 0104-0106
(2020/11/23)
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- Transition-Metal-Free Approach to Polysubstituted Furans
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A convenient and straightforward strategy for the synthesis of 2,3-disubstituted and 2,3,5-trisubstituted furans via a base-promoted domino reaction of β-keto compounds with vinyl dichlorides is described. This transition-metal-free approach proceeds under operationally simple reaction conditions featuring easily available starting materials, a broad substrate scope, and good functional group tolerance.
- You, Changming,Zhang, Zhenming,Tu, Yongliang,Tang, Hong,Wang, Yuanfeng,Long, Da,Zhao, Junfeng
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p. 3902 - 3910
(2020/03/23)
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- Preparation method and application of pongamol
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The invention belongs to the field of medicinal chemistry, and relates to a preparation method and application of pongamol. The preparation method comprises the following steps: with 1,3-cyclohexanedione (6) as a starting raw material, carrying out a cyclization reaction to obtain 6,7-dihydro-4-(5H)-benzofuranone (7); carrying out acylation reaction on the compound (7) to obtain 5-acetyl-6,7-dihydro-4-(5H)-benzofuranone (8); carrying out dehydrogenation reaction on the compound (8) to obtain 1-(4-hydroxy-5-benzofuryl) ethyl ketone (3); carrying out methylation reaction on the compound (3) to obtain 1-(4-methoxy-5-benzofuryl) ethyl ketone (4); and condensing the compound (4) with benzoyl chloride to obtain the pongamol. According to the preparation method, the selected reagents are cheap and easy to obtain, the post-treatment method is simple, the reaction conditions are mild, and the product yield is high. Pharmacological activity experiments show that the synthesized compound has nerve injury resistance and anti-inflammatory activity, which means that the compound has a good application prospect in the field of treatment of nerve injury and inflammation related diseases.
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Paragraph 0008; 0089-0091
(2019/10/01)
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- Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate
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We have explored here the scope of the age-old diethyl malonate-based accesses to α-amino esters involving Knoevenagel condensations of diethyl malonate on aldehydes, reductions of the resulting alkylidenemalonates, the preparation of the corresponding α-hydroxyimino esters and their final reduction. This synthetic pathway turned out to be general although some unexpected limitations were encountered. The synthetic modifications of some of the intermediates - using Suzuki-Miyaura coupling or cycloadditions - before undertaking the oximation step - provided accesses to further α-amino esters. Moreover, other pathways to α-hydroxyimino esters were explored including an attempt to improve the cycloadditions between ethyl β-bromo-α-hydroxyiminocarboxylate and various alkylfuranes.
- Coutant, Eloi P.,Hervin, Vincent,Gagnot, Glwadys,Ford, Candice,Baatallah, Racha,Janin, Yves L.
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supporting information
p. 2853 - 2860
(2018/11/26)
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- Investigation of furo[2,3-h]- and pyridazino[3,4-f]cinnolin-3-ol scaffolds as substrates for the development of novel HIV-1 integrase inhibitors
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With the aim to develop novel HIV-1 integrase inhibitors, we obtained a set of condensed ring systems based on the furo[2,3-h]cinnolin-3(2H)-one and pyridazino[3,4-f]cinnolin-3-ol scaffolds bearing a potential chelating pharmacophore, which can be involved in the inhibition mechanism of the enzyme. Herein, we report the design, synthesis, structural investigation and preliminary biological results of these heteroaromatic systems. ARKAT-USA, Inc.
- Gomaa, Mohamed F. Y.,Pala, Nicolino,Derudas, Marco,Hasanen, Jehan Abd-Elrazik,El-Tamany, El-Sayed H.,Casule, Paola,Mariani, Alberto,Sechi, Mario
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experimental part
p. 1 - 14
(2011/06/19)
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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
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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 AgBF4
- Xia, Likai,Lee, Yong Rok,Kim, Sung Hong,Lyoo, Won Seok
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p. 1554 - 1558
(2011/12/14)
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- Site- and stereoselectivity in the photochemical oxetane formation reaction (Paterno-Buechi reaction) of tetrahydrobenzofuranols with benzophenone: hydroxy-directed diastereoselectivity?
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The Paterno-Buechi reactions of tetrahydrobenzofuranols with benzophenone were investigated to reveal site- and stereo-selectivity in oxetane formation reactions. Both selectivities were found to be largely dependent on the reaction temperature. The trans selectivity increased with a decrease in temperature, and the more-substituted oxetanes were selectively formed at high temperature. Copyright
- Yabuno, Youhei,Hiraga, Yoshikazu,Abe, Manabu
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p. 822 - 823
(2008/12/22)
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- Synthesis and structure-activity relationships of a series of substituted 2-(1H-furo[2,3-g]indazol-1-yl)ethylamine derivatives as 5-HT2C receptor agonists
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A series of novel indazole derivatives were synthesized, and their structure-activity relationships examined in order to identify potent and selective 5-HT2C receptor agonists. Among these compounds, (S)-2-(7-ethyl-1H-furo[2,3-g]indazol-1-yl)-1-methylethylamine (YM348) had a good in vitro profile, that is, high agonistic activity to the human 5-HT2C receptor subtype (EC50 = 1.0 nM) and high selectivity over 5-HT2A receptors. This compound was also effective in a rat penile erection model when administered po.
- Shimada, Itsuro,Maeno, Kyoichi,Kazuta, Ken-ichi,Kubota, Hideki,Kimizuka, Tetsuya,Kimura, Yasuharu,Hatanaka, Ken-ichi,Naitou, Yuki,Wanibuchi, Fumikazu,Sakamoto, Shuichi,Tsukamoto, Shin-ichi
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p. 1966 - 1982
(2008/09/21)
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- Synthesis and biological studies of novel 2-aminoalkylethers as potential antiarrhythmic agents for the conversion of atrial fibrillation
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A series of 2-aminoalkylethers prepared as potential antiarrhythmic agents is described. The present compounds are mixed sodium and potassium ion channel blockers and exhibit antiarrhythmic activity in a rat model of ischemia-induced arrhythmias. Structure-activity studies led to the identification of three compounds 5, 18, and 26, which were selected based on their particular in vivo electrophysiological properties, for studies in two canine atrial fibrillation (AF) models. The three compounds converted AF in both models, but only compound 26 was shown to be orally bioavailable. Resolution of the racemate 26 into its corresponding enantiomers 40 and 41 and subsequent biological testing of these enantiomers led to the selection of (1S,2S)-1-(1-naphthalenethoxy)-2-(3- ketopyrrolidinyl)cyclohexane monohydrochloride (41) as a potential atrial selective antiarrhythmic candidate for further development.
- Plouvier, Bertrand,Beatch, Gregory N.,Jung, Grace L.,Zolotoy, Alexander,Sheng, Tao,Clohs, Lilian,Barrett, Terrance D.,Fedida, David,Wang, Wei Q.,Zhu, Jeff J.,Liu, Yuzhong,Abraham, Shlomo,Lynn, Leah,Dong, Ying,Wall, Richard A.,Walker, Michael J. A.
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p. 2818 - 2841
(2008/02/09)
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- 3-PHENOXY-4-PYRIDAZINOL DERIVATIVE AND HERBICIDE COMPOSITION CONTAINING THE SAME
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A compound represented by the formula: wherein R1 represents a hydrogen atom, a halogen atom, alkyl group, etc., ???R2 represents a hydrogen atom, a halogen atom, alkyl group, etc., ???R3, R4, R5, R6 and R7 each independently represent a hydrogen atom, a halogen atom, a substitutable alkyl group, a substitutable alkenyl group, alkynyl group, a substitute-able cycloalkyl group, etc., or adjacent two of R3, R4, R5, R6 and R7 may together with the carbon atoms to which the respective substituents are bonded form a ring which may be substituted, ???m and n each independently represent 0 or 1, a salt thereof or an ester derivative thereof; an agricultural chemical containing the same as an active ingredient; and a herbicidal composition containing the compound and a second herbicidally active compound as active ingredients.
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- An efficient preparative route to 7-ethyl-1H-furo[2,3-g]indazole
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A new and efficient route to 7-ethyl-1H-furo[2,3-g]indazole (2) has been developed. Treatment of 4,5-dihydro-7-(1-hydroxyethyl)indazole (12) with hydrochloric acid in ethanol resulted in a concomitant dehydration and aromatization to afford the title compound in good yield.
- Shimada, Itsuro,Maeno, Kyoichi,Kimizuka, Tetsuya,Goto, Seiki,Takahashi, Takumi,Nakamura, Atsushi,Miyafuji, Akio,Tsukamoto, Shin-Ichi,Sakamoto, Shuichi
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p. 807 - 813
(2007/10/03)
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- Efficient synthesis of dihydrofurans with sulfide groups by ceric(IV) ammonium nitrate-mediated oxidative cycloaddition of 1,3-dicarbonyl compounds to vinyl sulfides. Application to the synthesis of benzo[b]naphtho[2,3-d]furan-6,11-dione and first total synthesis of millettocalyxins C and pongamol methyl ether
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Ceric(IV) ammonium nitrate-mediated oxidative cycloaddition of 1,3-dicarbonyls to vinyl sulfides afforded substituted dihydrofurans with sulfide groups in moderate yields. This new synthetic method has been applied to the synthesis of benzo[b]naphtho[2,3-d]furan-6,11-dione and furanoflavone natural products such as millettocalyxins C and pongol methyl ether.
- Lee, Yong Rok,Kang, Keon Yong,Lee, Gun Joon,Lee, Won Kyong
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p. 1977 - 1988
(2007/10/03)
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- Facile strategy to 3-acylfurans by silver(I)/celite-mediated cycloaddition of 1,3-dicarbonyl compounds to vinyl sulfides. First total synthesis of α-clausenan
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An efficient synthesis of 3-acylfurans is achieved by silver((I)/Celite-mediated cycloaddition of dicarbonyl compounds, with vinyl sulfides.
- Lee Yong Rok, R.,Kim, Nam Suk,Kim, Byung So
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p. 5671 - 5674
(2007/10/03)
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- Construction of three types of fused isoindoles via furan-pyrrole ring exchange reaction
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The new synthetic route of three types of fused isoindoles using furan- pyrrole ring exchange reaction as the main synthetic strategy is presented. Benzoisoindoles 17, 28 and 38 were synthesised from bicyclic furans 14, 25 and 35 respectively, which were trapped with dimethyl acetylenedicarboxylate.
- Lee, Mase,Moritomo, Hiroyuki,Kanematsu, Ken
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p. 8169 - 8180
(2007/10/03)
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- A NEW ROUTE FOR THE SYNTHESIS OF FURANOFLAVONE AND FURANOCHALCONE NATURAL PRODUCTS
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An efficient synthesis of furanoflavones and furanochalcones has been carried out starting from a dihydrobenzofuran derivative.Key Words: Total synthesis, lanceolatin B, pongaglabrone, isopongaglabol, isopongaglabol methyl ether, pongol, pongamol, ovalite
- Lee, Yong Rok,Morehead, Andrew T.
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p. 4909 - 4922
(2007/10/02)
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- Synthesis of patulin and its cyclohexane analogue from furan derivatives
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Patulin, a mycotoxin from fungi of Penicillium and Aspergillis species, and its cyclohexane analogue were synthesized concisely via oxidation of furan derivatives, followed by cyclization to give a ylidenebutenolide ring.
- Tada,Ohtsu,Chiba
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p. 2167 - 2169
(2007/10/02)
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- Dipolar Cycloaddition of Rhodium Carbenoids with Vinyl Esters. Total Synthesis of Pongamol and Lanceolatin B.
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A new method for dipolar cycloaddition of diazocyclohexane-1,3-diones, leading to benzofuran derivatives, has been applied to the total synthesis of natural products from Tephrosia and Pongamia.
- Pirrung, Michael C.,Lee, Yong Rok
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p. 6231 - 6234
(2007/10/02)
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- A CONVENIENT SYNTHESIS OF 4-HYDROXYBENZO-(B)-FURAN, (KARANJOL)
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The synthesis of karanjol from tetrahydro-(b)-furan intermediates is described.
- Kneen, Geoffrey,Maddocks, Peter J.
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p. 1635 - 1640
(2007/10/02)
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- Chemistry of 2H-3,1-Benzoxazine-2,4(1H)-dione (Isatoic Anhydride).16 . Facile Construction of the Furacridone Ring System
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The synthesis of the furacridone ring skeleton was accomplished in one step by the reaction of N-methylisatoic anhydride (7) with the lithium enolate derived from 6,7-dihydro-4(5H)-benzofuranone (10).Aromatization of the C ring with DDQ furnished 5-dehydroxyfuracridone (6).
- Coppola, Gary G.
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p. 1569 - 1570
(2007/10/02)
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- A FACILE SYNTHESIS OF 4-OXO-4,5,6,7-TETRAHYDROINDOLES
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Condensation of 1,3-cyclohexanedione with chloroacetaldehyde followed by dehydration gave 4-oxo-4,5,6,7-tetrahydrobenzofuran in a good yield.The tetrahydrobenzofuran was quantitatively converted into 4-oxo-4,5,6,7-tetrahydroindoles.
- Matsumoto, Masakatsu,Watanabe, Nobuko
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p. 2313 - 2316
(2007/10/02)
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