- Preparation method of 2-amino substituted six-membered nitrogen-containing heterocycle complex
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The invention discloses a preparation method of a 2-amino substituted six-membered nitrogen-containing heterocycle complex. The preparation method comprises the following steps: mix 2-fluorine substituted six-membered nitrogen-containing heterocycle complex and amidine hydrochloride salt compound, and then react under the action of a alkaline substance to obtain a 2-amino substituted six-memberednitrogen-containing heterocycle complex. Preferably, the 2-amino substituted six-membered nitrogen-containing heterocycle complex is a 2-amino pyridine compound, a 2-aminopyrimidine compound or a 2-aminopyrazine compound. Compared with the prior art, the method has the advantages of simple synthesis conditions, less reaction steps, mild reaction conditions, low cost of the catalyst used, less waste discharge and good functional group tolerance.
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Paragraph 0025; 0026
(2019/02/08)
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- Transition-metal-free access to 2-aminopyridine derivatives from 2-fluoropyridine and acetamidine hydrochloride
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Under catalyst-free conditions, an efficient method for the synthesis of 2-aminopyridine derivatives through the nucleophilic substitution and hydrolysis of 2-fluoropyridine and acetamidine hydrochloride has been developed. This amination uses inexpensive acetamidine hydrochloride as the ammonia source and has the advantages of a high yield, high chemoselectivity and wide substrate adaptability. The results suggest that other N-heterocycles containing fluorine substituents can also complete the reaction via these reaction conditions and yield the target products.
- Li, Yibiao,Huang, Shuo,Liao, Chunshu,Shao, Yan,Chen, Lu
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supporting information
p. 7564 - 7567
(2018/11/02)
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- One-Pot Access to Benzo[a]carbazoles via Palladium(II)-Catalyzed Hetero- and Carboannulations
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A Pd(II)-catalyzed direct synthesis of benzo[a]carbazoles has been achieved through aminopalladation of alkynes, followed by intramolecular nucleophilic addition of the generated carbon-palladium bond to a tethered cyano/aldehyde group. Compared to literature procedures, this synthetic approach is operationally simple, uses simple substrates, and offers a fast intramolecular assembly resulting in the direct synthesis of benzo[a]carbazoles in which a wide variation of substituents at different sites is well-tolerated, leaving enough opportunity for diversification.
- Jash, Moumita,Das, Bimolendu,Chowdhury, Chinmay
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supporting information
p. 10987 - 10999
(2016/11/28)
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- Potassium 4-iodylbenzenesulfonate: Preparation, structure, and application as a reagent for oxidative iodination of arenes
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A new hypervalent iodine(V) compound, potassium 4-iodylbenzenesulfonate, was prepared by the oxidation of 4-iodobenzensulfonic acid with Oxone in water. This potassium salt can be further converted into 4-iodylbenzenesulfonic acid by treatment with the acidic form of Amberlyst 15 in water. A single-crystal X-ray structure of potassium 4-iodylbenzenesulfonate revealed the presence of polymeric chains in the solid state due to a combination of numerous intra- and intermolecular interactions. Potassium 4-iodylbenzenesulfonate will likely find many practical applications as a thermally stable and water-soluble hypervalent iodine-based oxidant, particularly useful as a reagent for oxidative iodination of aromatic substrates. This reagent can be effectively recovered from the reaction mixture (92 % recovery) by treatment of the aqueous layer with Oxone at 60°C for 2 h, followed by filtration of the precipitate. A new hypervalent iodine(V) compound, potassium 4-iodylbenzenesulfonate, was prepared by oxidation of 4-iodobenzenesulfonic acid with Oxone in water. This new reagent promises many practical applications as a thermally stable, water-soluble and recyclable hypervalent iodine oxidant, particularly useful for oxidative iodination of aromatic substrates.
- Yusubov, Mekhman S.,Yusubova, Roza Y.,Nemykin, Victor N.,Maskaev, Andrey V.,Geraskina, Margarita R.,Kirschning, Andreas,Zhdankin, Viktor V.
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p. 5935 - 5942,8
(2020/09/02)
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- Remarkable switch in the regiochemistry of the iodination of anilines by N-iodosuccinimide: Synthesis of 1,2-dichloro-3,4-diiodobenzene
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Direct iodination of anilines by NIS in polar solvents (such as DMSO) affords p-iodinated products with up to >99% regioselectivity. Switching to less polar solvents (such as benzene) in the presence of AcOH inverts this outcome toward dramatically increased or preferential generation of the o-isomers, also with up to >99% regioselectivity. This finding was exploited in the synthesis of 1,2-dichloro-3,4-diiodobenzene. Georg Thieme Verlag Stuttgart - New York.
- Shen, Hao,Vollhardt, K. Peter C.
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supporting information; experimental part
p. 208 - 214
(2012/03/11)
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- PYRIDINE DERIVATIVE CONTAINING ((PHOSPHONOOXY)METHYL)PYRIDINIUM RING, AND ANTIFUNGAL AGENT CONTAINING THESE DERIVATIVE
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The present invention provides an antifungal agent that has excellent antifungal action, and is also superior in terms of its properties, and particularly its solubility in water and safety in an aqueous solution, and its in vivo pharmacokinetics and safety. According to the present invention, there is provided a compound represented by the following formula (I), or a salt thereof: wherein R1 represents a hydrogen atom, a halogen atom, an amino group, a C1-6 alkyl group, a C1-6 alkoxy group, or a C1-6 alkoxy C1-6 alkyl group; R2 represents a hydrogen atom, a C1-6 alkyl group, an amino group, or a di-C1-6 alkylamino group;R3 represents a hydrogen atom, a halogen atom, or a C1-6 alkyl group; andR4 represents a hydrogen atom, a halogen atom, or a C1-6 alkyl group.
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Page/Page column 10
(2011/01/05)
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- Single bifunctional ruthenium catalyst for one-pot cyclization and hydration giving functionalized indoles and benzofurans
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Chemical equation Presented Bifunctional is more than twice as fun! At low loading, catalyst 1 (see scheme) can form two important heterocycle classes, apparently by attack of XH on a vinylidene intermediate. Aza- and nitroindoles can be formed, and all N-protecting groups tested (alkyl, allyl, sulfonyl) were tolerated. The newly formed ring can be deuterated in one step, and for substrates with two terminal alkynes, cyclization can be followed by hydration, making this catalyst uniquely versatile.
- Nair, Reji N.,Lee, Paul J.,Rheingold, Arnold L.,Grotjahn, Douglas B.
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supporting information; scheme or table
p. 7992 - 7995
(2010/09/18)
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- Aza-Tryptamine Substrates in Monoterpene Indole Alkaloid Biosynthesis
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Biosynthetic pathways can be hijacked to yield novel compounds by introduction of novel starting materials. Here we have altered tryptamine, which serves as the starting substrate for a variety of alkaloid biosynthetic pathways, by replacing the indole with one of four aza-indole isomers. We show that two aza-tryptamine substrates can be successfully incorporated into the products of the monoterpene indole alkaloid pathway in Catharanthus roseus. Use of unnatural heterocycles in precursor-directed biosynthesis, in both microbial and plant natural product pathways, has not been widely demonstrated, and successful incorporation of starting substrate analogs containing the aza-indole functionality has not been previously reported. This work serves as a starting point to explore fermentation of aza-alkaloids from other tryptophan- and tryptamine-derived natural product pathways.
- Lee, Hyang-Yeol,Yerkes, Nancy,O'Connor, Sarah E.
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scheme or table
p. 1225 - 1229
(2010/07/10)
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- Spirocyclic Azaindole Derivatives
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The invention relates to substituted azaindole derivatives, to methods for the production thereof, to medicaments containing said compounds and to the use of substituted azaindole derivatives for producing medicaments.
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Page/Page column 17
(2009/07/03)
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- PYRIDINE DERIVATIVES SUBSTITUTED BY HETEROCYCLIC RING AND PHOSPHONOAMINO GROUP, AND ANTI-FUNGAL AGENT CONTAINING SAME
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Anti-fungal agent having excellent anti-fungal action physicochemical properties including safety and water solubility. Compound represented by formula (I), or salt thereof: wherein R1 represents hydrogen, halogen, amino, R11-NH- wherein R11 represents C1-6 alkyl, hydroxy C1-6 alkyl, C1-6 alkoxy C1-6 alkyl, or C1-6alkoxycarbonyl C1-6 alkyl, R12-(CO)-NH- wherein R12 represents C1-6 alkyl group or C1-6 alkoxy C1-6 alkyl, C1-6 alkyl, hydroxy C1-6 alkyl, cyano C1-6 alkyl, C1-6 alkoxy, or C1-6 alkoxy C1-6 alkyl or a phosphonoamino group; R2 represents hydrogen, C1-6 alkyl, amino, or a di C1-6 alkylamino group or a phosphonoamino group; one of X and Y is nitrogen while the other is nitrogen or oxygen; ring A represents a 5- or 6-member heteroaryl ring or a benzene ring which may have a halogen atom or 1 or 2 C1-6 alkyl groups; Z represents a single bond, a methylene group, an ethylene group, oxygen, sulfur, -CH2O-, -OCH2-, -NH-, -CH2NH-, -NHCH2-, -CH2S-, or -SCH2-; R3 represents hydrogen or halogen or C1-6 alkyl, C3-8 cycloalkyl, C6-10 aryl, a 5- or 6-member heteroaryl group or a 5- or 6-member nonaromatic heterocyclic group which may have 1 or 2 substituents; and R4 represents hydrogen or halogen; provided that either R1 or R2 represents a phosphonoamino group.
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Page/Page column 51
(2009/04/24)
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- PYRIDINE DERIVATIVE SUBSTITUTED BY HETEROARYL RING, AND ANTIFUNGAL AGENT COMPRISING THE SAME
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The present invention provides an antifungal agent that has excellent antifungal action, and is also excellent in terms of its properties, safety, and metabolic stability. The present invention discloses a compound represented by the following formula I or a salt thereof, and an antifungal agent comprising the compound or the salt: wherein R1 represents a hydrogen atom, a halogen atom, an amino group, a C1-6 alkyl group, a C1-6 alkoxy group, or a C1-6-alkoxy-C1-6-alkyl group; R2 represents a hydrogen atom or an amino group; X, Y, Z, and W independently represent a nitrogen atom, an oxygen atom, a sulfur atom, or -CH-, provided that at least two among X, Y, and W are nitrogen atoms; the ring A represents a 5- or 6-membered heteroaryl ring or a benzene ring; Q represents a methylene group, an oxygen atom, -CH2O-, -OCH2-, -NH-, -NHCH2-, or -CH2NH-; and R3 represents a C1-6 alkyl group, a C3-8 cycloalkyl group, a C6-10 aryl group, or a 5- or 6-membered heteroaryl group, each of which may have one or two substituents.
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Page/Page column 60-61
(2009/06/27)
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- HETEROCYCLE-SUBSTITUTED PYRIDINE DERIVATIVE'S SALT OR CRYSTAL THEREOF
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There is provided a heterocycle-substituted pyridine derivative's salt or a crystal thereof. The present invention provides an acid addition salt of 3-(3-(4-(pyridin-2-yloxymethyl)-benzyl)-isoxazol-5-yl)-pyridin-2-yl amine or a crystal thereof as well as
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Page/Page column 4-5
(2008/12/08)
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- Syntheses of pyrido[1,2-a][1,3,5]triazin-4-one C-deoxyribonucleosides
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We achieved the syntheses of new C-deoxyribonucleosides bearing pyrido[1,2-a][1,3,5]triazin-4-one derivatives using palladium-catalyzed Heck-type coupling. Some of these C-deoxyribonucleosides were able to convert to phosphoramidite reagents, which can be
- Oda, Hiroshi,Hanami, Takeshi,Iwashita, Takashi,Kojima, Miki,Itoh, Masayoshi,Hayashizaki, Yoshihide
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p. 11021 - 11029
(2008/02/12)
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- Heterocycles substituted pyridine derivatives and antifungal agent containing thereof
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An object of the present invention is to provide an antifungal agent which has excellent antifungal effects and is superior in terms of its physical properties, safety and metabolic stability. According to the present invention, there is disclosed a compound represented by the following formula (I), or a salt thereof: wherein R1 represents a hydrogen atom, a halogen atom, an amino group, a C1-6 alkyl group, a C1-6 alkoxy group or a C1-6 alkoxy C1-6 alkyl group; R2 represents a hydrogen atom, a C1-6 alkyl group, an amino group or a di C1-6 alkylamino group; one of X and Y is a nitrogen atom while the other is a nitrogen atom or an oxygen atom; ring A represents a 5- or 6-member heteroaryl ring or a benzene ring which may have a halogen atom, or 1 or 2 C1-6 alkyl groups; Z represents a single bond, a methylene group, an ethylene group, an oxygen atom, a sulfur atom, —CH2O—, —OCH2—, —NH—, —CH2NH—, —NHCH2—, —CH2S—, or —SCH2—; R3 represents a hydrogen atom, a halogen atom, a C1-6 alkyl group, a C3-8 cycloalkyl group, a C6-10 aryl group, a 5- or 6-member heteroaryl group, or 5- or 6-member non-aromatic heterocyclic group which may have 1 or 2 substituents; and R4 represents a hydrogen atom or a halogen atom.
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Page/Page column 53
(2010/11/27)
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- Method for synthesis of AZA-annelated pyrroles, thiophenes, and furans
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Methods of synthesis of intermediates that are useful as bioisosteres of the indole, benzofuran and benzothiophene scaffold are disclosed.
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Page/Page column 8
(2008/06/13)
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- Metalation/SRN1 Coupling in Heterocyclic Synthesis. A Convenient Methodology for Ring Functionalization
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Lithiation, iodination, and fluorine substitution on 2-fluoropyridine gave 2-substituted 3-iodopyridines, which were further subjected to iodine SRN1 substitution by carbon, sulfur, and phosphorus nucleophiles.Iodine substitution by enolates on 2-amino-3-iodopyridines afforded ketones, which were further cyclized to various 1,2-disubstituted pyrrolopyridines. 2-Amino-3-iodo-, 3-amino-4-iodo, and 4-amino-3-iodopyridines were prepared by directed metalation of 2-, 3-, and 4-(pivaloylamino)pyridines.Substitution of iodine by enolates under SRN1 conditions and acidic cyclization led to various 2-substituted pyrrolo, --, and -pyridines in high yields.
- Estel, L.,Marsais, F.,Queguiner, G.
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p. 2740 - 2744
(2007/10/02)
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- Condensed Heteroaromatic Ring Systems. IV. Synthesis of Naphthyridine Derivatives by Cyclization of Aminopyridineacrylic Esters
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The reaction of aminohalopyridines with ethyl acrylate in the presence of palladium(II)acetate and triarylphosphine gave ethyl aminopyridineacrylates.The cyclization of the resulting acrylates under basic conditions gave naphthyridinones having a carbostyril-type moiety.Keywords- intramolecular cyclization; palladium catalyst; ethyl acrylate; naphthyridinone; pyridineacrylic ester
- Sakamoto, Takao,Kondo, Yoshinori,Yamanaka, Hiroshi
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p. 4764 - 4768
(2007/10/02)
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