Synthesis of benzimidazoles in high-temperature water

作者: Lucinda M. Dudd , Eleni Venardou , Eduardo Garcia-Verdugo , Peter Licence , Alexander J. Blake

DOI: 10.1039/B212394K

关键词: AutoclaveSolventDiffractionOrganic chemistryChemical engineeringBenzoic acidSpectroscopyChemistryYield (chemistry)In situ

摘要: The objective of this research was to conduct constructive organic chemistry in water and achieve yields that were comparable to, or better than, those conventional media. synthesis 2-phenylbenzimidazole from 1,2-phenylenediamine benzoic acid chosen as a benchmark reaction. reaction parameters, such temperature, density time, have been systematically studied understand whether the solvent properties high-temperature can positive effect on chemistry. performed new design batch-type autoclave also monitored situ by UV-vis spectroscopy. By tuning yield has optimised around 90%. conditions then applied related benzimidazoles, some which crystallised solution single crystals sufficiently pure be analysed directly X-ray diffraction, without any further purification.

参考文章(22)
H Al-Muhaimeed, A Parallel-Group Comparison of Astemizole and Loratadine for the Treatment of Perennial Allergic Rhinitis Journal of International Medical Research. ,vol. 25, pp. 175- 181 ,(1997) , 10.1177/030006059702500401
John Mann, Anne Baron, Yaw Opoku-Boahen, Eric Johansson, Gary Parkinson, Lloyd R. Kelland, Stephen Neidle, A new class of symmetric bisbenzimidazole-based DNA minor groove-binding agents showing antitumor activity. Journal of Medicinal Chemistry. ,vol. 44, pp. 138- 144 ,(2001) , 10.1021/JM000297B
Tao Xiang, Keith P. Johnston, Acid-base behavior in supercritical water: β-naphthoic acid-ammonia equilibrium Journal of Solution Chemistry. ,vol. 26, pp. 13- 30 ,(1997) , 10.1007/BF02439441
Michael Siskin, Alan R. Katritzky, Reactivity of organic compounds in superheated water: general background. Chemical Reviews. ,vol. 101, pp. 825- 836 ,(2001) , 10.1021/CR000088Z
Yutaka Ikushima, Kiyotaka Hatakeda, Osamu Sato, Toshirou Yokoyama, Masahiko Arai, Acceleration of Synthetic Organic Reactions Using Supercritical Water: Noncatalytic Beckmann and Pinacol Rearrangements Journal of the American Chemical Society. ,vol. 122, pp. 1908- 1918 ,(2000) , 10.1021/JA9925251
Alan R Katritzky, Daniel A Nichols, Michael Siskin, Ramiah Murugan, Marudai Balasubramanian, None, Reactions in High-Temperature Aqueous Media Chemical Reviews. ,vol. 101, pp. 837- 892 ,(2001) , 10.1021/CR960103T
Carmen Boix, Jesús Martínez de la Fuente, Martyn Poliakoff, Preparation of quinolines by reduction of ortho-nitroarenes with zinc in near-critical water New Journal of Chemistry. ,vol. 23, pp. 641- 643 ,(1999) , 10.1039/A902554E
William L. Marshall, E. U. Franck, Ion Product of Water Substance, 0-1000 C, 1-10,000 Bars. New International Formulation and Its Background, Journal of Physical and Chemical Reference Data. ,vol. 10, pp. 295- 304 ,(1981) , 10.1063/1.555643