| 词条 | Debus-Radziszewski imidazole synthesis |
| 释义 |
| Name = Debus-Radziszewski imidazole synthesis | Type = Ring forming reaction | NamedAfter = Heinrich Debus Bronisław Leonard Radziszewski }} The Debus-Radziszewski imidazole synthesis is an organic reaction used for the synthesis of imidazoles from a dicarbonyl, an aldehyde, and ammonia. The dicarbonyl component is commonly glyoxal, but can also include various 1,2-diketones and ketoaldehydes. The method is used commercially to produce several imidazoles.[1] The process is an example of a multicomponent reaction. The reaction can be viewed as occurring in two stages. In the first stage, the dicarbonyl and ammonia condense to give a diimine (shown with unusual orientation of N-H groups): In the second stage, this diimine condenses with the aldehyde: This reaction is named after Heinrich Debus[2] and Bronisław Leonard Radziszewski.[3][4] A modification of this general method, where one equivalent of ammonia is replaced by an amine, affords N-substituted imidazoles in good yields.[5] References1. ^Ebel, K., Koehler, H., Gamer, A. O., & Jäckh, R. "Imidazole and Derivatives." In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH, {{DOI|10.1002/14356007.a13_661}} 2. ^{{cite journal | title = Ueber die Einwirkung des Ammoniaks auf Glyoxal | journal = Justus Liebigs Annalen der Chemie | doi = 10.1002/jlac.18581070209 | year = 1858 | last1 = Debus | first1 = Heinrich | volume = 107 | issue = 2 | pages = 199}} 3. ^{{cite journal | title = Ueber Glyoxalin und seine Homologe | journal = Berichte der deutschen chemischen Gesellschaft | doi = 10.1002/cber.188201502245 | year = 1882 | last1 = Radzisewski | first1 = Br. | volume = 15 | issue = 2 | pages = 2706}} 4. ^On the development of organic chemistry in Ukraine Dmytro O. Tymoshenko ARKIVOC 2005 (viii) 1-3 Link 5. ^{{US patent reference|number=6,177,575|y=2001|m=01|d=23|inventor=A. J. Arduengo|title=Process for Manufacture of Imidazoles}} 2 : Nitrogen heterocycle forming reactions|Name reactions |
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