- Selectfluor facilitated bridging of indoles to bis(indolyl)methanes using methyl: Tert -butyl ether as a new methylene precursor
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A novel, green and efficient method is developed for the synthesis of methylene bridged bis(indolyl)methanes in good to excellent yields. The reaction employs methyl tert-butyl ether (MTBE) as the methylene source and selectfluor as an oxidizing agent. The scope and versatility of the methods have been successfully demonstrated with 48 examples. The metal-free transformation process is suitable for scale-up production. A selectfluor-promoted oxidative reaction mechanism is proposed based on the results of the experimental studies. This journal is
- Jin, Jiang,Li, Yinghua,Xiang, Shiqun,Fan, Weibin,Guo, Shiwei,Huang, Deguang
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p. 4076 - 4081
(2021/05/19)
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- Preparation method of tetraethyl michler's ketone
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The invention provides a preparation method of tetraethyl michler's ketone. N, N'-diethyl aniline is taken as a raw material and is subjected to condensation with formaldehyde to obtain intermediate 4,4'-diphenyl methane (diphenylamine) diphenylmethane, and tetraethyl michler's ketone is obtained by oxidizing the intermediate. The preparation method has the advantages of cheap and available raw materials, low reaction temperature, good solubility of the reaction intermediate, good reaction yield, simple and convenient in operation and suitable for industrial production.
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Paragraph 0019; 0022; 0025; 0028
(2018/03/26)
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- Highly regioselective para-methylthiolation/bridging methylenation of arylamines promoted by NH4I
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Aryl methyl thioethers and methylene-bridged arylamines were synthesized via highly regioselective para-methylthiolation/bridging methylenation of arylamines using DMSO as the methylthio or methylene source in the presence of NH4I under metal-free conditions. For the substrates with both electron-donating and electron-withdrawing substituents, the reaction proceeded smoothly and gave moderate to good yields.
- Xu, Yinfeng,Cong, Tiantian,Liu, Ping,Sun, Peipei
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supporting information
p. 9742 - 9745
(2015/10/05)
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- Copper(II)-catalyzed C-H (sp3) oxidation and C-N cleavage: Synthesis of methylene-bridged compounds using TMEDA as a carbon source in water
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A green, simple, and efficient protocol for the selective methylenation via CuCl2/oxygen-mediated C-H (sp3) oxidation and C-N cleavage using tetramethylethylenediamine (TMEDA) as a carbon source has been developed. The reactions were achieved in green solvent water under atmospheric conditions. The protocol exhibited a broad substrate scope including indoles, anilines, pyrroles and 1,3-dicarbonyls. Furthermore, two key intermediates of the reaction were successfully identified and the mechanism was explored. The Royal Society of Chemistry 2013.
- Zhao, Dan,Wang, Yue,Zhu, Min-Xue,Shen, Qi,Zhang, Lei,Du, Yun,Li, Jian-Xin
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p. 10272 - 10276
(2013/09/02)
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- Cu(ii)-catalyzed C-H (SP3) oxidation and C-N cleavage: Base-switched methylenation and formylation using tetramethylethylenediamine as a carbon source
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Base-switched methylenation and formylation using tetramethylethylenediamine (TMEDA) as a carbon source have been achieved under mild conditions, catalyzed by CuCl2, with atmospheric oxygen as oxidant. Bisindolylmethanes, diphenylmethanes and 3-formylindoles were synthesized with excellent regioselectivity and good yield.
- Zhang, Lei,Peng, Chen,Zhao, Dan,Wang, Yue,Fu, Hai-Jian,Shen, Qi,Li, Jian-Xin
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supporting information; experimental part
p. 5928 - 5930
(2012/07/27)
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- Synthesis and photochromic properties of substituted naphthopyran compounds
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A group of 3,3-diaryl-3H-naphtho[2,1-b]pyran compounds with functional substituents at the 5- and 6-positions of the naphthopyran skeleton and the para positions at the 3-aryl moieties were prepared through condensation reactions between 2-naphthol derivatives and 1,1-diarylprop-2-yn-1-ol derivatives. The chemical structures of the compounds were confirmed by NMR and MS. The crystal structure of 3,3-diphenyl-6-morpholino-3H-naphtho[2,1-b]pyran (4b) was determined and the relationship between the pyran substructure and photochromism was discussed. The photochromic properties were studied as well, and decoloration kinetics of colored forms was fitted to the biexponential model. Among these compounds, 4b was considered to be the best one due to the large ΔOD of colored form, which is one of the most important properties used in the photochromic material.
- Wang, Zhen,Meng, Qinghua,Zhang, Zhihui,Fu, Dingliang,Zhang, Wanbin
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experimental part
p. 2246 - 2250
(2011/04/22)
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- 3,6-DISUBSTITUTED XANTHYLIUM SALTS
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This invention pertains generally to processes, uses, methods and materials utilising particular xanthylium compounds, including compounds of formula (I) and (II), as further defined herein. These compounds are useful as drugs, for example, in the treatment of tauopathies, such as Alzheimer's disease.
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Page/Page column 75
(2010/07/02)
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- Benzotriazole Mediated Synthesis of Methylenebisanilines
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Methylenebisanilines and methylenebis(N,N-dialkylaniline)s are prepared by the reactions of 1-hydroxymethylbenzotriazole with anilines and with N,N-dialkylanilines under acidic conditions.Isolation of the intermediate 4-(benzotriazol-1-ylmethyl)anilines and the N,N-dialkyl analogues and their reactions with anilines allow the efficient preparation of both symmetrical and unsymmetrical members of both product classes.
- Katritzky, Alan R.,Lan, Xiangfu,Lam, Jamshed N.
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p. 341 - 346
(2007/10/02)
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- Effect of Substituents on the Reaction of Aromatic Amines and Formaldehyde in Acid Medium
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The kinetics and mechanism of the condensation of N- and C-substituted aromatic amines with formaldehyde in acid medium have been studied using quantitative TLC technique, and the first order rate constants and relative reactivities calculated.In all cases where para-position is free, 4-aminobenzyl alcohols are the initial products.These undergo condensation with amines to give 4-(4-aminobenzyl)anilines.The effect of substituents on the reactivity of amines has been discussed.
- Nayar, Mazhuvadyil R. Gopinathan,Francis, Joseph D.
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p. 776 - 780
(2007/10/02)
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- Alkylidene Transfer from Monochloroalkylmercury(II) Compounds to Aromatic Amines; Selective C-Alkylation
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αα-Diarylalkane derivatives have been synthesized from monochloroalkylmercury(II) compounds in a noncarbenoid alkylidene transfer reaction which takes place selectively on the aromatic ring.A mechanism is suggested for this process.Intermediate products are prepared by alternative routes to ascertain their participation in the course of the reaction.As a consequence, two different aryl groups can be successively incorporated into the alkane molecule.
- Barluenga, Jose,Campos, Pedro J.,Roy, Miguel A.,Asensio, Gregorio
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p. 1420 - 1426
(2007/10/02)
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