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However, the use of dichloromethane is avoided since it can generate highly explosive azido-chloromethane and diazidomethane. The reaction may also instead be conducted in toluene, [3] acetonitrile, or pyridine. [4] Tf 2 O + NaN 3 → TfN 3 + NaOTf (Tf = CF 3 SO 2) An alternative route starts from imidazole-1-sulfonyl azide. [5]
Preparation [ edit ] 3-Aminopyridine is prepared by heating nicotinamide with sodium hypobromite ( Hofmann rearrangement ), which is in turn prepared in situ by the reaction of sodium hydroxide and bromine at 70 °C.
The Kröhnke pyridine synthesis provides a fairly general method for generating substituted pyridines using pyridine itself as a reagent which does not become incorporated into the final product. The reaction of pyridine with bromomethyl ketones gives the related pyridinium salt, wherein the methylene group is highly acidic.
Upon metabolism, 1,4-DHP based antihypertensive drugs undergo oxidation by way of cytochrome P-450 in the liver and are thus converted to their pyridine derivatives. [11] As a result, particular attention has been paid to the aromatization of 1,4-DHPs as a means to understand biological systems and so as to develop new methods of accessing ...
2-Picoline was the first pyridine compound reported to be isolated in pure form. It was isolated from coal tar in 1846 by T. Anderson. [2] This chemistry was practiced by Reilly Industries. [3] It is now mainly produced by two principal routes. One method involves the condensation of acetaldehyde and ammonia in the presence of an oxide catalyst ...
The method also affords some 2-methylpyridine. 4-Methylpyridine is of little intrinsic value but is a precursor to other commercially significant species, often of medicinal interest. For example, ammoxidation of 4-methylpyridine gives 4-cyanopyridine, the precursor to a variety of other derivatives such as the antituberculosis drug isoniazid. [1]
With secondary amines and not primary amines the Zincke reaction takes on a different shape forming so-called Zincke aldehydes in which the pyridine ring is ring-opened with the terminal iminium group hydrolyzed to an aldehyde: [4] Zincke aldehydes. This variation has been applied in the synthesis of novel indoles: [11] Zincke aldehydes Kearney ...
The Chichibabin pyridine synthesis (/ ˈ tʃ iː tʃ iː ˌ b eɪ b iː n /) is a method for synthesizing pyridine rings. The reaction involves the condensation reaction of aldehydes, ketones, α,β-Unsaturated carbonyl compounds, or any combination of the above, with ammonia. [1] It was reported by Aleksei Chichibabin in 1924.
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