- Synthesis of 2-methyl-1-[(5-methylfuran-2-yl)methyl]- and 2-methyl-1-[(5-methylpyrrol-2-yl)methyl]-1H-benzimidazoles
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A method for the synthesis of 2-methyl-1-[(5-methylfuran-2-yl)methyl]-1H- benzimidazoles based on the intramolecular cyclization of vicinal N-[(5-methylfuran-2-yl)methyl]aminoanilides has been developed. A study was carried out on the protolytic opening o
- Stroganova,Red'Kin,Kovalenko,Vasilin,Krapivin
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p. 1264 - 1273
(2014/01/17)
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- AN IMPROVED PROCESS FOR MANUFACTURE OF SUBSTITUTED BENZIMIDAZOLES
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The present invention relates to a process for the production of benzimidazole derivatives comprising providing an amino acetamido benzene derivative; and condensing and cyclising the aminoacetamido benzene derivative in the presence of a base and in the presence of a cyclising agent under conditions effective to form the benzimidazole derivative. The acetamido benzene derivative has the formula (I) wherein R is OMe or OCHF2. The resulting substituted benzimidazoles are key intermediates in the synthesis of H+/K+-ATPase irreversible inhibitors, most particularly Omeprazole.
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- Synthesis and pharmacological evaluation of isoindolo[1,2-b]quinazolinone and isoindolo[2,1-a]benzimidazole derivatives related to the antitumor agent batracylin
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The synthesis and pharmacological activity of isoindolo[1,2-b]quinazolin- 12(10H)-ones and isoindolo[2,1-a]benzimidazoles related to batracylin are described. The acute toxicity of batracyclin has been associated with the formation of its N-acetyl metabolite which is a potent inducer of unscheduled DNA synthesis in rat hepatocytes. The desamino derivative and the 8-aza analog of batracylin retained the ability to inhibit topoisomerase II but did not induce unscheduled DNA synthesis. While less active than batracylin, these analogs were cytotoxic to CCRF CEM leukemia cells. The isoindolo[2,1- a]benzimidazole derivatives were inactive as topoisomerase II inhibitors and, in general, failed to exhibit comparable antitumor activity or to induce unscheduled DNA synthesis.
- Meegalla,Stevens,McQueen,Chen,Yu,Liu,Barrows,LaVoie
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p. 3434 - 3439
(2007/10/02)
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- o-Nitrobenzylidene Compounds. Part 4. The Cyanide-induced Cyclisation of o-Acetamido-N-(o-nitrobenzylidene)anilines: an Improved Route to Quinoxalinocinnolines
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Cyclisation of o-acetamido-N-(o-nitrobenzylidene)anilines (7) with potassium cyanide in methanol (preferably under nitrogen) leads in most cases to quinoxalinocinnolines (6) of unambiguous substitution pattern.In some cases, cyclisation appears to be incomplete, and 2-amino-3-(o-nitrophenyl)quinoxalines (11) are obtained as by-products; in certain cases quinoxalinocinnoline 5-oxides (10) are also detected.These by-products are assumed to result from oxidation of intermediates in the cyclisation process (7) ----> (6).
- Shepherd, Thomas,Smith, David M.
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p. 501 - 506
(2007/10/02)
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- Synthesis of N-Acetylbenzimidazole Derivatives
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For the structure determination of thiazolobenzimidazol-3(2H)-one derivatives (2 or 3) they were converted to the corresponding 1-acetylbenzimidazoles (4) by desulfurization.The latter compounds (4) were alternatively prepared by the cyclization of 2-aminoacetanilide derivatives (5) with CS2 in dimethylformamide (DMF), followed by desulfurization with Raney Ni.However, the reactions of 5 with ethyl orthoformate/H2SO4 in DMF gave a mixture of 4 and its acetyl-rearranged product (7).Keywords-acetyl group; rearrangement; thiazolobenzimidazol-3(2H)-one; N-acetylbenzimidazoles; ethyl orthoformate; carbon disulfide; desulfurization
- Tanaka, Kenjiro,Shimazaki, Michiko,Murakami, Yasuoki
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p. 2714 - 2722
(2007/10/02)
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