614-31-3Relevant articles and documents
Synthesis of new pyrrolo[3,4-b]indol-3-ones as latent substrates for pyrrolo[3,4-b]indoles
Saulnier, Mark G.,Schreiber, Steven M.,Cavanaugh, Kerri L.,Perni, Robert B.,Joyner, H. Howard,Gribble, Gordon W.
, p. 15 - 23 (2020/11/19)
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.
Preparation of Hexahydrocarbazole Derivatives by Reductive Indolization
Christoffers, Jens,Dierks, Anna,Fliegel, Lukas,Schmidtmann, Marc
, p. 7164 - 7175 (2020/11/30)
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.
Rh(iii)-catalyzed, hydrazine-directed C-H functionalization with 1-alkynylcyclobutanols: A new strategy for 1: H -indazoles
Zhang, Lei,Chen, Junyu,Chen, Xiahe,Zheng, Xiangyun,Zhou, Jian,Zhong, Tianshuo,Chen, Zhiwei,Yang, Yun-Fang,Jiang, Xinpeng,She, Yuan-Bin,Yu, Chuanming
, p. 7415 - 7418 (2020/07/15)
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
Preparation method of mebhydrolin napadisylate
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Paragraph 0023; 0026; 0027; 0030; 0033; 0034, (2019/06/30)
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.
A synthetic approach to (±)-aristomakine
Perni, Robert B.,Gribble, Gordon W.
, p. 75 - 84 (2018/07/03)
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.
Reductive Hydrazination with Trichlorosilane: A Method for the Preparation of 1,1-Disubstituted Hydrazines
Wang, Tao,Di, Xiao,Wang, Chao,Zhou, Li,Sun, Jian
supporting information, p. 1900 - 1903 (2016/05/19)
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.
2,3′-Bis(1′H-indole) heterocycles: New p53/MDM2/MDMX antagonists
Neochoritis, Constantinos G.,Wang, Kan,Estrada-Ortiz, Natalia,Herdtweck, Eberhardt,Kubica, Katarzyna,Twarda, Aleksandra,Zak, Krzysztof M.,Holak, Tad A.,D?mling, Alexander
supporting information, p. 5661 - 5666 (2015/11/24)
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.
Formation of enehydrazine intermediates through coupling of phenylhydrazines with vinyl halides: Entry into the Fischer indole synthesis
Zhan, Fuxu,Liang, Guangxin
supporting information, p. 1266 - 1269 (2013/03/13)
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
Photoinduced cleavage of N-N bonds of aromatic hydrazines and hydrazides by visible light
Zhu, Mingzhao,Zheng, Nan
, p. 2223 - 2236 (2011/09/15)
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.
Discovery of ectoparasiticidal hydrazonotrifluoromethanesulfonanilides
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
scheme or table, p. 649 - 652 (2010/06/12)
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.
