- Synthesis of new pyrrolo[3,4-b]indol-3-ones as latent substrates for pyrrolo[3,4-b]indoles
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We report the synthesis of new examples of the 1,4-dihydropyrrolo[3,4-b]indol-3(2H)-one ring system via Fischer indolization between the appropriate phenylhydrazines and pyrrolidine-2,3-diones. Lithiation at the C-1 position with lithium diisopropylamide following by quenching with iodomethane affords 1-methyl-1,4-dihydropyrrolo[3,4-b]indol-3(2H)-ones in excellent yield.
- Saulnier, Mark G.,Schreiber, Steven M.,Cavanaugh, Kerri L.,Perni, Robert B.,Joyner, H. Howard,Gribble, Gordon W.
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- Preparation of Hexahydrocarbazole Derivatives by Reductive Indolization
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The reductive indolization is a two-step protocol performed in one flask: First, the acid-mediated Fischer indolization of a cyclic ketone with phenylhydrazine forms an iminium ion which is subsequently reduced by a hydrido borate reagent to the indoline as the final product. We utilized this new strategy for the preparation of hexahydrocarbazole derivatives with a side chain in the quaternary C4a-position. Starting materials were several N1- and aryl-substituted phenylhydrazines and a cyclic ketone with propanoic ester moiety, which is the product of the conjugated addition of cyclohexanone to ethyl acrylate. Furthermore, benzannulated congeners as well as a pyrido[4,3-b]indole derivative were accessed. The hexahydrocarbazole defines a molecular scaffold with two points of diversification. Therefore, several derivatives at N9 and at the C4a-side chain were prepared.
- Christoffers, Jens,Dierks, Anna,Fliegel, Lukas,Schmidtmann, Marc
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p. 7164 - 7175
(2020/11/30)
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- Rh(iii)-catalyzed, hydrazine-directed C-H functionalization with 1-alkynylcyclobutanols: A new strategy for 1: H -indazoles
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Rh(iii)-catalyzed coupling of phenylhydrazines with 1-alkynylcyclobutanols was realized through a hydrazine-directed C-H functionalization pathway. This [4+1] annulation, based on the cleavage of a Csp-Csp triple bond in alkynylcyclobutanol, provides a new pathway to prepare diverse 1H-indazoles under mild reaction conditions. This journal is
- Zhang, Lei,Chen, Junyu,Chen, Xiahe,Zheng, Xiangyun,Zhou, Jian,Zhong, Tianshuo,Chen, Zhiwei,Yang, Yun-Fang,Jiang, Xinpeng,She, Yuan-Bin,Yu, Chuanming
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p. 7415 - 7418
(2020/07/15)
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- Preparation method of mebhydrolin napadisylate
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The invention belongs to the field of drug synthesis and provides a preparation method of mebhydrolin napadisylate. The preparation method is characterized by including the steps of firstly, subjecting methyl imine-N,N-methyl dipropionate and sodium methylate to heating under the effect of an organic solvent to achieve loop closing, and using hydrochloric acid to performing heating decarboxylationto obtain N-methyl-4-piperidone hydrochloride; subjecting phenylhydrazine and benzyl chloride to condensation under an alkaline condition to obtain benzyl phenylhydrazine; thirdly, mixing the N-methyl-4-piperidone hydrochloride solution and the benzyl phenylhydrazine, heating to generate mebhydrolin hydrochloride, adding disodium 1,5-naphthalenedisulfonate to obtain the mebhydrolin napadisylate.The preparation method is high in yield, mild in reaction conditions, convenient in intermediate purification and capable of satisfying the requirements of industrial production.
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Paragraph 0023; 0026; 0027; 0030; 0033; 0034
(2019/06/30)
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- A synthetic approach to (±)-aristomakine
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We describe the synthesis of trans-11b-methyl-2,3,4,6,11,11b-hexahydro-1H-benzo[a]carbazol-3-ol (2) in five steps from the Wieland-Miescher ketone 3 in 17% overall yield. The N-benzyl analogue (trans-11-Benzyl-11b-methyl-2,3,4,6,11,11b-hexahydro-1H-benzo[a]carbazol-3-ol) 15 was likewise prepared. Attempts thus far to fashion (±)-aristomakine (1) from 2, 15, or derivatives have not been successful.
- Perni, Robert B.,Gribble, Gordon W.
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- Reductive Hydrazination with Trichlorosilane: A Method for the Preparation of 1,1-Disubstituted Hydrazines
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A straightforward and facile method has been developed to prepare 1,1-disubstituted hydrazines via Lewis base promoted direct reductive hydrazination. Under the catalysis of hexamethylphosphoramide (HMPA) and N,N-dimethylacetamide (DMAc), respectively, various ketones and aldehydes could react with phenylhdrazines to prepare 1,1-disubstituted hydrazines with good to high yields.
- Wang, Tao,Di, Xiao,Wang, Chao,Zhou, Li,Sun, Jian
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supporting information
p. 1900 - 1903
(2016/05/19)
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- 2,3′-Bis(1′H-indole) heterocycles: New p53/MDM2/MDMX antagonists
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The protein-protein interaction of p53 and MDM2/X is a promising non genotoxic anticancer target. A rapid and efficient methodology was developed to synthesize the 2,3′-bis(1′H-indole) heterocyclic scaffold 2 as ester, acid and amide derivatives. Their binding affinity with MDM2 was evaluated using both fluorescence polarization (FP) assay and HSQC experiments, indicating good inhibition and a perfect starting point for further optimizations.
- Neochoritis, Constantinos G.,Wang, Kan,Estrada-Ortiz, Natalia,Herdtweck, Eberhardt,Kubica, Katarzyna,Twarda, Aleksandra,Zak, Krzysztof M.,Holak, Tad A.,D?mling, Alexander
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supporting information
p. 5661 - 5666
(2015/11/24)
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- Formation of enehydrazine intermediates through coupling of phenylhydrazines with vinyl halides: Entry into the Fischer indole synthesis
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Cut to the chase: Direct formation of an enehydrazine, an intermediate in the classic Fischer indole synthesis, solves the regioselectivity problem associated with indolization. This approach not only achieves selective synthesis of indoles through proper selection of the vinyl halide, but also leads to quick construction of desoxyeseroline and esermethole, as well as the key structural motif in the Akuammiline alkaloid vincorine. Copyright
- Zhan, Fuxu,Liang, Guangxin
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supporting information
p. 1266 - 1269
(2013/03/13)
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- Photoinduced cleavage of N-N bonds of aromatic hydrazines and hydrazides by visible light
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A photocatalytic system involving [Ru(bpyrz)(PFH, visible light, and air has been developed for cleavage of the N-N bonds of hydrazines and hydrazides. This catalytic system is generally effective for N,N-disubstituted hydrazine and hydrazide derivatives, including arylhydrazides, N-alkyl-N-arylhydrazines, and N,N-diarylhydrazines. The utility of this cleavage reaction has been demonstrated by synthesizing a variety of secondary aromatic amines. Georg Thieme Verlag Stuttgart ? New York.
- Zhu, Mingzhao,Zheng, Nan
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p. 2223 - 2236
(2011/09/15)
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- Discovery of ectoparasiticidal hydrazonotrifluoromethanesulfonanilides
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A series of hydrazonotrifluorosulfonanilide derivatives were synthesized and evaluated for in vitro activity against the ectoparasites Ctenocephalides felis and Rhipicephalus sanguineus. Some compounds with excellent activity against tick were identified.
- Ali, Abdelselam,Fisara, Petr,Freemont, Jamie A.,Kyi, Stella,Meyer, Adam G.,Riches, Andrew G.,Sargent, Roger M.,Sawutz, David G.,Turner, Kathleen A.,Winzenberg, Kevin N.,Yang, Qi
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scheme or table
p. 649 - 652
(2010/06/12)
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- A convenient synthesis of 1-alkyl-1-phenylhydrazines from N-aminophthalimide
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N-Alkylaminophthalimides were synthesized by condensation of N-aminophthalimide with aldehydes, and subsequent reduction of the intermediate with pyridine-borane in acetic acid. N-Phenylation and removal of the phthalimide group gave 1-alkyl-1-phenylhydrazines in high yield.
- Nara, Shigeru,Sakamoto, Takeshi,Miyazawa, Etsuko,Kikugawa, Yasuo
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- MEDICINAL COMPOSITION
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The present invention is composed of a pharmaceutical composition for the therapy of nephritis which comprises an amide derivative represented by the following formula [1] or pharmaceutically acceptable salt thereof, as an active ingredient: ???wherein R1 and R2 may be the same or different and each is hydrogen, alkyl which may be substituted, acyl, aryl which may be substituted, or an aromatic heterocyclic group which may be substituted; R3, R4, R5 and R6 may be the same or different and each is hydrogen, halogen, hydroxy, amino which may be substituted, alkyl which may be substituted, alkoxy or nitro and the like; and R7 represents cyclic amino which may be substituted or azabicycloalkylamino which may be substituted. The pharmaceutical composition of the invention is useful for the therapy of nephritis.
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- AMIDE DERIVATIVES AND DRUG COMPOSITIONS
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The present invention is composed of an amide derivative represented by the following formula [1] or pharmaceutically acceptable salt thereof: ???wherein R1 and R2 may be the same or different and each is hydrogen, alkyl which may be substituted, acyl, aryl which may be substituted, or an aromatic heterocyclic group which may be substituted; R3, R4, R5, and R6 may be the same or different and each is hydrogen, halogen, hydroxy, amino which may be substituted, alkyl which may be substituted, alkoxy, or nitro and the like; and R7 represents cyclic amino which may be substituted or azabicycloalkylamino which may be substituted, and a pharmaceutical composition which comprises it as an active ingredient. The compound of the invention is useful as an inhibitor of TGF-β production or an antagonist of TGF-β.
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- Investigation of the Potential of Molybdenum(VI) Hydrazido(2-) Complexes as Sources of Nitrenium Ions: Cleavage of the N-N Bond and Incorporation of the β-Nitrogen Group into Solvent Molecules
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Photolyis or thermolysis of bis(N,N-dimethyldithiocarbamato)bismolybdenum(VI) complexes in 1,1,2,2-tetrachloroethane results predominantly in transfer of the hydrazido group to the solvent with formation of dichloroacetohydrazides.A small amount of the corresponding dichloroacetamides are produced by N-N cleavage and N(R)Ph transfer.In contrast, the latter process dominates the reaction of dichlorobis(N,N-dimethyldithiocarbamato)mono-molybdenum(VI) complexes with silver nitrate in alcohols occuring concomitantly with ring methoxylation and nitration and N-nitrosation.Neither transfer of N(R)Ph appears to involve free nitrenium ions.
- Baum, Marc M.,Smith, Edward H.
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p. 2513 - 2520
(2007/10/02)
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- SIMPLE PREPARATION OF N-ALKYL-N-ARYLHYDRAZINES FROM DIAZOTABLE N-ARYLAMINES
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Phase-Transfer-catalyzed N-alkylation of arylhydrazones 2, followed by hydrazinolysis with hydrazine hydrate in the presence of concentrated hydrochloric acid, provides a new access to N-alkyl-N-arylhydrazines 3.
- Gonzalez, Asensio
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p. 1225 - 1230
(2007/10/02)
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- Use of phenyl hydrazines for seed biostimulation or the treatment of lipoxygenase mediated seed deteriorations
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The present invention provides a method of treating certain deleterious conditions mediated by the action of lipoxygenases in mammals and seeds using certain phenyl hydrazines. Also provided is a method for seed biostimulation using these phenyl hydrazines.
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- An efficient synthesis of 1,1-disubstituted hydrazines
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1,1-disubstituted hydrazines were prepared from the corresponding 1,1-disubstituted ureas by means of the Hofmann rearrangement reaction. The yields were fairly good, except from the ureas susceptible to oxidation, and thus the present method represents an additional and efficient procedure for the synthesis of 1,1-disubstituted hydrazines.
- Murakami,Yokoyama,Sasakura,Tamagawa
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p. 423 - 428
(2007/10/02)
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- Fischer Indole Synthesis of 3-Acyl and 3-Alkoxy-carbonylindoles
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N-Benzyl-N-phenylhydrazine derivatives of 1,3-diketones and 1,3-ketoesters undergo normal Fischer cyclisations to indoles, but no method could be found for the subsequent removal of the N-protecting group.No method could be found for the indolisation of N-aroyl-N-phenylhydrazine derivatives of dimedone with retention of the N-protecting group, though heating in tetralin did effect the electrocyclic step of the Fischer sequence and the formation of a carbon-carbon bond.
- Mills, Keith,Khawaja, Ibtisam K. Al,Al-Saleh, Fowzia,Joule, John A.
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p. 636 - 641
(2007/10/02)
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