- Pd-tBuONO Cocatalyzed Aerobic Indole Synthesis
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A Pd-tBuONO co-catalyzed scalable and practical synthesis of indoles with molecular oxygen as terminal oxidant is developed. Either terminal or internal 2-vinylanilines could be smoothly converted to desired indoles under one general condition. This method has been evaluated in the large scale synthesis of indomethacin and a potential anti-breast cancer drug candidate 1. (Figure presented.).
- Ning, Xiao-Shan,Liang, Xin,Hu, Kang-Fei,Yao, Chuan-Zhi,Qu, Jian-Ping,Kang, Yan-Biao
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supporting information
p. 1590 - 1594
(2018/04/30)
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- Synthesis of indolines via a SmI2 promoted domino nitro reduction-intramolecular aza-Michael reaction
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A simple and straightforward synthesis of substituted indolines based on a domino nitro reduction intramolecular aza-Michael reaction is described. The reaction employs Samarium diiodide under mild conditions for the addition of dibromoacetic acid to substituted 2-(2-nitrophenyl) acetaldehyde derivatives and their subsequent cyclization upon nitro group reduction to provide corresponding indoline heterocycles in good yields. This "one pot" strategy also permitted the expeditious synthesis of a 1,2,3,4-tetrahydroquinoline, whereas the seven-membered 2,3,4,5-tetrahydrobenzoazepines compounds were not formed under these reaction conditions.
- Ramos, Josierika A. Ferreira,Araújo, Carolina S.,Nagem, Tanus J.,Taylor, Jason G.
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- Development of isomerization and cycloisomerization with use of a ruthenium hydride with N-heterocyclic carbene and its application to the synthesis of heterocycles
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A pure ruthenium hydride complex with N-heterocyclic carbene (NHC) ligand was efficiently generated from the reaction of a second-generation Grubbs ruthenium catalyst with vinyloxytrimethylsilane and unambiguously characterized. This ruthenium hydride complex showed high catalytic activity for the selective isomerization of terminal olefin and for the cycloisomerization of 1,6-dienes. These reactions of N-allyl-o-vinylaniline lead to novel synthetic methods for heterocycles such as indoles and 3-methylene-2,3-dihydroindoles, which are useful synthons for bioactive natural products. These procedures address an important issue in diversity-oriented synthesis.
- Arisawa, Mitsuhiro,Terada, Yukiyoshi,Takahashi, Kazuyuki,Nakagawa, Masako,Nishida, Atsushi
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p. 4255 - 4261
(2007/10/03)
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- Cycloisomerization promoted by the combination of a ruthenium-carbene catalyst and trimethylsilyl vinyl ether, and its application in the synthesis of heterocyclic compounds: 3-Methylene-2,3-dihydroindoles and 3-methylene-2,3- dihydrobenzofurans
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Substituted N and O heterocycles have been synthesized by the cycloisomerization of dienes using a ruthenium-carbene catalyst. The products obtained with and without trimethylsilyl vinyl ether differ (see scheme, Cy = cyclohexyl, Mes = 2,4,6-trimethylphenyl, Ts = p-toluenesulfonyl).
- Terada, Yukiyoshi,Arisawa, Mitsuhiro,Nishida, Atsushi
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p. 4063 - 4067
(2007/10/03)
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- [1,4]DIAZOCINO [7,8,1-hi]INDOLE DERIVATIVES AS ANTIPSYCHOTIC AND ANTIOBESITY AGENTS
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Compounds of formula (1) are provided: (1) where R1 through R7 are defined herein. The compounds of formula (I) are 5HT2c agonists or partial agonists, and are useful for treating a variety of disorders.
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Page/Page column 30-31
(2008/06/13)
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- A new method for the synthesis of 2,6-dinitro and 2-halo-6-nitrostyrenes
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A new method for the synthesis of 2-halo-6-nitrostyrenes from 2-halo-6-nitrotoluenes is disclosed. Also described is a one-pot process for the synthesis of 2,6-dinitristyrene from 2,6-dinitrotoluene. (C) 2000 Elsevier Science Ltd.
- Mundla
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p. 6319 - 6321
(2007/10/03)
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- Nucleoside derivatives with photolabile protective groups
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The invention relates to nucleoside derivatives having photolabile protective groups of the general formula (I) STR1 in which R1 =H, NO2, CN, OCH3, halogen or alkyl or alkoxyalkyl having 1 to 4 C atoms R2 =H, OCH3 R3 =H, F, Cl, Br, NO2 R4 =H, halogen, OCH3, or an alkyl radical having 1 to 4 C atoms R5 =H or a usual functional group for preparing oligonucleotides R6 =H, OH, halogen or XR8, where X=O or S and R8 represents a protective group usual in nucleotide chemistry, B=adenine, cytosine, guanine, thymine, uracil, 2,6-diaminopurin-9-yl, hypoxanthin-9-yl, 5-methylcytosin-1-yl, 5-amino-4-imidazolcarboxamid-1-yl, or 5-amino-4-imidazolcarboxamid-3-yl, where in the case of B=adenine, cytosine or guanine, the primary amino function optionally exhibits a permanent protective group. These derivatives may be used for the light-controlled synthesis of oligonucleotides on a DNA chip.
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- New photolabile protecting groups in nucleoside and nucleotide chemistry - Synthesis, cleavage mechanisms and applications
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New photolabile protecting groups have been found in the 2-(2- nitrophenyl)ethoxycarbonyl and the 2-(2-nitrophenyl)ethylsulfonyl group, respectively. The influence of substituents at the phenyl ring as well as the side-chain has been investigated regarding the photolysis rates on irradiation at 365 mn. β-Branching in the side-chain leads to highly increased rates of photodeprotection. A new type of photocleavage mechanism consisting of a photoinduced β-elimination process is proposed.
- Giegrich,Eisele-Buehler,Hermann,Kvasyuk,Charubala,Pfleiderer
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p. 1987 - 1996
(2007/10/03)
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- L-4-Chlorotryptophan from Immature Seeds of Pisum sativum and Reassignment of the Absolute Stereochemistry of N-Malonyl-4-chlorotryptophan
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Free 4-chlorotryptophan (4-Cl-Trp) was isolated from immature seeds of P. sativum, identified, and its stereochemistry determined to be L-form.Reinvestigation of the N-malonyl-4-Cl-Trp isolated from the same seeds showed that the stereochemistry of the 4-Cl-Trp residue is L-form.
- Sakagami, Youji,Manabe, Kan,Aitani, Takayuki,Thiruvikraman, S. V.,Marumo, Shingo
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p. 1057 - 1060
(2007/10/02)
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- Tricyclic compound or salts thereof, method for producing the same and antimicrobial agent containing the same
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A tricyclic compound represented by the general formula (1) and salts thereof. STR1 A method for producing the tricyclic compound and salts thereof, and an antimicrobial agent containing the tricyclic compound and salts thereof as an active ingredient are
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- Ruthenium-Catalyzed Dehydrogenative N-Heterocyclization: Indoles from 2-Aminophenethyl Alcohols and 2-Nitrophenethyl Alcohols
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Indole derivatives 3 were readily obtained from 2-aminophenethyl alcohols 1 in the presence of 2 mol percent (based on 1) of RuCl2(PPh3)3 under reflux in toluene.Indole (3a) was afforded from 2-aminophenethyl alcohol (1a) quantitatively.Other indoles (3) were also obtained in 73-99percent isolated yields from the corresponding 1, which were easily prepared by condensation between the corresponding 2-nitrotoluenes and aldehydes followed by reduction.During the reaction, a stoichiometric amount of hydrogen was spontaneously evolved into the gas phase.With a heterogeneous and homogeneous binary catalyst system, indoles were afforded in one pot from 2-nitrophenethyl alcohols 2 under a hydrogen atmosphere.
- Tsuji, Yasushi,Kotachi, Shinji,Huh, Keun-Tae,Watanabe, Yoshihisa
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p. 580 - 584
(2007/10/02)
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