243668-26-0Relevant articles and documents
Compositions containing five-membered unsaturated heterocyclic structure of the α, β unsaturated ketone compound and its preparation method and application
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, (2017/07/14)
The invention provides alpha, beta unsaturated ketone compounds containing benzo five-membered unsaturated heterocycle structures as well as a preparation method and an application and use of the compounds. The alpha, beta unsaturated ketone compounds containing the benzo five-membered unsaturated heterocycle structures have the structure of a formula (I). In addition, the invention further provides a method for preparing the compounds and a pharmaceutical composition containing the components as active components. In vitro activity tests show that the compounds provided by the invention show a remarkable inhibiting effect on tumor cells. Therefore, the invention lays a foundation for lucubrating and developing anti-tumor medicines in the future and meanwhile further provides a new technical means for treating tumor diseases.
A New Facile Sulfenylation of 2-Acetylbenzimidazoles
Kumar, P. Praveen,Dathu Reddy,Ramana Reddy, Ch. Venkata,Rama Devi,Dubey
, p. 1775 - 1779 (2015/10/29)
A facile sulfenylation of 2-acetylbenzimidazoles has been achieved by using N-(phenylthio)phthalimide in the presence of potassium tert-butoxide in DMSO. The latter gave N-alkyl-β-phenylsulfenyl-2-acetylbenzimidazole on reaction with alkylating agents in the presence of potassium carbonate in N,N-dimethylformamide.
A green and simple synthesis of N-alkyl-2-acetylbenzimidazoles
Kumar, P. Kishore,Dubey
experimental part, p. 3249 - 3250 (2012/08/29)
A green and simple synthesis of N-alkyl-2-substituted benzimidazoles has been developed. In this method, 2-acetyl benzimidazole compound (1) was alkylated with reagents such as dimethyl sulfate/diethyl sulfate/benzyl chloride under green conditions i.e., by physical grinding in presence of a mild base like K2CO3 or by using green solvents like PEG-600, ethanol etc. or by using micro-wave irradiation technique to obtain N-alkyl-2-acetylbenzimidazoles compound (2).
Alkylation studies on pyrazolyl and isoxazolyl benzimidazoles
Kumar, Kishore,Hemasunder,Naidu,Dubey
, p. 393 - 398 (2013/09/24)
2-Acetylbenzimidazole (1) on heating with dimethyl formamide dimethyl acetal gave 1-(1 H-benzimidazolyl)-3-dimethylaminopropenone (2) which on reaction with hycirazpne hydrate gave 2-(1 H-pyrazolyl)-1 H-benzimidazole (3), The reaction of 3 with DMS/DES/ PhCH2CI in CH3CN containing K2CO3 as base and triethylbenzylammonium chloride (TEBAC) as phase trasfer catalyst (PTC) resulted in the formation of 2-(3-pyrazolyl)-1 - substitutedbenzimidazole (4). Alkylation of I with DMS/DES/PhCH2CI under PTC conditions gave the previously known 1-substituted -2-acetyl benzimidazoles (5) which with DMF-DMA gave I -substituted-2-(2-benzimidazolyl)-3.dimethylaminopropenone (6). The latter could also be obtained from 2 by alkylation under PTC conditions. Treatment of 6 with hydrazine hydrate in methanol yielded 4. Reaction of 2 with hydroxylammonium chloride yielded 1 H-(2-benzimidazolyl)-3-isoxazole (8) which on alkylation under PTC conditions gave 1-substituted (2-benzimidazolyl)-3-isoxazole (9). The latter could also be obtained from 6 by treatment with hydroxylammonium chloride.
Synthesis of novel benzimidazole β-keto sulfones and β-hydroxy sulfones and their regiospecific alkylation studies
Dubey,Kumar, N.D. Mahesh,Chaitanya,Naidu,Vineel, B. George
body text, p. 937 - 943 (2010/10/18)
The synthesis of benzimidazole β-keto sulfides 5a-f by the reaction of W-alkyl-α-bromo-2-acetylberizirnidazoles 3a-b with 5-substituted- benzimidazole-2-thiols 4a-c followed by successive oxidation with H 2O2 to give β-keto sulfones 8a-f and reduction with NaBH4 to give β-hydroxy sulfones 9a-f is described. Reaction of 5a, 8a, 9a and 10a with DMS in the presence of K2CO3 and TBAB as PTC, resulted in the regiospecific N-methylation of benzimidazole moiety of 12a, 11a, 14a and 13a respectively.
Benzimidazolium dichromates: Efficient reagents for selective oxidation of alcohols to carbonyl compounds
Ramaiah,Dubey,Ramanatham,Kumar, C. Ravi,Grossert
, p. 1765 - 1767 (2007/10/03)
Benzimidazolium dichromates have been used for the selective and efficient oxidation of simple alcohols to carbonyl compounds. 2-Methylbenzimidazolium dichromate has been used as a standard compound. It has been found to oxidize selectively, primary alcohols to aldehydes, without any over-oxidation, and secondary alcohols to ketones. Of the several solvents explored, acetic acid at RT has been found to be the best medium for oxidation.
Solid phase synthesis of benzimidazole ketones and benzimidazole chalcones under solvent-free conditions
Dubey,Kumar, C. Ravi,Babu, Balaji
, p. 3128 - 3130 (2007/10/03)
Oxidation of 1-alkyl/aralkyl-2-(α-hydroxyalkyl/aryl)benzimidazoles 1 with KMnO4 on neutral alumina under solid phase conditions gives the corresponding ketones, 1-alkyl/aralkyl-2-acyl-benzimidazoles 2. Compound 2a (R2 = CH3) on condensation with aromatic aldehydes in the presence of solid NaOH under solvent-free conditions, yields the corresponding chalcones, 1-alkyl/aralkyl-2-benzimidazole aryl vinyl ketone 3.
An unusual resistance to α-bromination by arylacetyl compound: Studies on bromination of 2-acetylbenzimidazoles and their subsequent reactions with sulphur nucleophiles - Synthesis of novel β-ketosulphone derivatives of benzimidazoles
Ramaiah,Dubey,Ramanatham,Grossert,Hooper
, p. 302 - 307 (2007/10/03)
Condensation of o-phenylenediamine with lactic acid under Phillips' conditions gave the known 2(α-hydroxyethyl)benzimidazole 1 which on oxidation with acid dichromate furnishes 2-acetylbenzimidazole 2. Reaction of 2 with bromine in acetic acid at room temp. give a novel product 3 but not the expected 2-(α-bromoacetyl)benzimidazole 4. Rational explanation is offered for this anamolous behaviour of 2. Compound 2 on alkylation, give 1- alkyl derivatives which undergo smooth bromination with bromine in acetic acid to give the corresponding 1-alkyl-2(α-bromoacetyl)benzimidazoles. Reactions of latter with sulphur nucleophiles such as PhS-, ArSO2- etc., resulting in substitution of bromine, leading to novel β-ketosulphone derivatives of benzimidazoles, are reported. Products have been characterised by IR, NMR (1H and 13C) and mass spectral data.
