- Efficient Access to Original 6-Substituted 5-Nitro-2,3-dihydro-imidazo[2,1- b ]oxazoles
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A one-pot sequential intramolecular cyclization and Suzuki-Miyaura or Sonogashira reaction under microwave irradiation are reported in the 5-nitro-2,3-dihydroimidazo[2,1- b ]oxazole series. The intramolecular cyclization of 1-(2,4-dibromo-5-nitro-1 H -imidazol-1-yl)propan-2-ol between the hydroxyethyl group and the bromine atom at the 2-position is carried out first, followed by optimization and generalization of the Suzuki-Miyaura and Sonogashira cross-coupling reactions of the bromine atom at the 4-position. The various boronic acids and alkynyl derivatives used to perform these palladium-catalyzed cross-coupling reactions allowed to substitute the 6-position of 5-nitro-2,3-dihydroimidazo[2,1- b ]oxazole compounds.
- Mathias, Fanny,Kabri, Youssef,Crozet, Maxime D.,Vanelle, Patrice
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- An improved kilogram-scale synthesis of 2-bromo-4-nitro-1H-imidazole: A key building block of nitroimidazole drugs
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An efficient two-step method for the synthesis of 2-bromo-4-nitroimidazole, 6, a key building block for nitroimidazole drugs, has been developed. The synthesis involves dibromination of 4-nitroimidazole 10 followed by selective debromination using in situ reductive deiodination strategy. The reactions are facile, safe, and easy to scale up. The large-scale applicability of this improved method was tested by conducting the reactions on kilogram scale to produce the desired product in high yield and quality.
- Pedada, Srinivasa Rao,Satam, Vijay S.,Tambade, Pawan J.,Kandadai, Srinivas A.,Hindupur, Rama Mohan,Pati, Hari N.,Launay, Delphine,Martin, Denis
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- A concise and sequential synthesis of the nitroimidazooxazole based drug, Delamanid and related compounds
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A concise, protection-group free and sequential route has been developed for the synthesis of the nitroimidazole based FDA-approved multi-drug resistant anti-tuberculosis drug, Delamanid and anti-leishmanial lead candidate VL-2098. The synthesis required
- Anand, Radhika,Cham, Pankaj Singh,Raina, Sushil,Sharma, Sumit,Singh, Parvinder Pal,Vishwakarma, Ram. A.
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p. 17085 - 17093
(2020/05/18)
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- An efficient one-pot catalyzed synthesis of 2,4-disubstituted 5-nitroimidazoles displaying antiparasitic and antibacterial activities
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A one-pot regioselective bis-Suzuki-Miyaura or Suzuki-Miyaura/Sonogashira reaction on 2,4-dibromo-1-methyl-5-nitro-1H-imidazole under microwave heating was developed. This method is applicable to a wide range of (hetero)arylboronic acids and terminal alkynes. Additionally, this approach provides a simple and efficient way to synthesize 2,4-disubstituted 5-nitroimidazole derivatives with antibacterial and antiparasitic properties.
- Mathias, Fanny,Kabri, Youssef,Okdah, Liliane,Giorgio, Carole Di,Rolain, Jean-Marc,Spitz, Cédric,Crozet, Maxime D.,Vanelle, Patrice
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- Bicyclic nitroimidazole derivatives, preparation method thereof and pharmaceutical composition for prevention or treatment of tuberculosis containing the same as an active ingredient
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The present invention relates to a bicyclic nitroimidazole derivative or a pharmaceutically acceptable salt thereof, a method for manufacturing the same, and a pharmaceutical composition comprising the same for preventing or treating tuberculosis. The novel bicyclic nitroimidazole derivative according to the present invention shows a superior antitubercular efficacy for tubercular bacillus in various environments, thereby can be used as a pharmaceutical composition for preventing or treating the tuberculosis.
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Paragraph 0082; 0083
(2017/03/08)
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- METHOD FOR PRODUCING 4-NITROIMIDAZOLE COMPOUND
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The present invention provides a method for producing a 4-nitroimidazole compound represented by general formula (1) at high yield and at high purity by a safe method causing few dangers such as explosion. The production method of the present invention comprises iodinating a 4-nitroimidazole compound represented by general formula (2): wherein each of X1 and X2 represents a chlorine atom or bromine atom, and then reducing the obtained 5-iodo-4-nitroimidazole compound represented by general formula (3): wherein X2 is the same as defined above.
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Page/Page column 72-73
(2008/06/13)
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- 1-SUBSTITUTED 4-NITROIMIDAZOLE COMPOUND AND PROCESS FOR PRODUCING THE SAME
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The present invention relates to a 1-substituted-4-nitroimidazole compound represented by the general formula (1) or a salt thereof, (wherein R is a hydrogen atom, a lower alkoxy group-substituted lower alkyl group, a phenyl-lower alkoxy group-substituted lower alkyl group, a cyano-substituted lower alkyl group, a phenyl-lower alkyl group which may have lower alkoxy groups as the substituents in the phenyl ring or a group of the formula -CH2RA; X is a halogen atom or a group of the formula -S(O)n-R1) and method for preparing the same. The compound of the formula (1) is a useful compound as an intermediate for synthesis of various pharmaceutical and agricultural chemicals, particularly, as intermediates for antitubercular agents.
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Page/Page column 46
(2010/02/12)
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