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The initially formed 2-chloropyridine reacts further to give 2,6-dichloropyridine. [2] Alternatively, 2-chloropyridines can be conveniently synthesized in high yields from pyridine-N-oxides. [3] 2-Chloropyridine was originally prepared by the chlorination of 2-hydroxypyridine with phosphoryl chloride. [4]
Chloropyridines are important intermediates to pharmaceuticals and agrochemicals. [1] A major use of 2-chloropyridine is the production of production of the fungicide pyrithione. Reaction of 4-chloropyridine with thioglycolic acid gives pyridylmercaptoacetic acid, a step in the production of cephalosporin antibiotics.
Protodeboronation is a well-known undesired side reaction, and frequently associated with metal-catalysed coupling reactions that utilise boronic acids (see Suzuki reaction). [1] For a given boronic acid, the propensity to undergo protodeboronation is highly variable and dependent on various factors, such as the reaction conditions employed and ...
The C–B bond of boronic acids and esters are slightly longer than typical C–C single bonds with a range of 1.55-1.59 Å. The lengthened C–B bond relative to the C–C bond results in a bond energy that is also slightly less than that of C–C bonds (323 kJ/mol for C–B vs 358 kJ/mol for C–C). [ 6 ]
Boronic acids are known to bind to active site serines and are part of inhibitors for porcine pancreatic lipase, [2] subtilisin [3] and the protease Kex2. [4] Furthermore, boronic acid derivatives constitute a class of inhibitors for human acyl-protein thioesterase 1 and 2, which are cancer drug targets within the Ras cycle. [5]
Compounds of the type BR n (OR) 3-n are called borinic esters (n = 2), boronic esters (n = 1), and borates (n = 0). Boronic acids are key to the Suzuki reaction. Trimethyl borate, debatably not an organoboron compound, is an intermediate in sodium borohydride production.
2,6-Dichloropyridine is a chloropyridine with the formula C 5 H 3 Cl 2 N. A white solid, it is one of six isomers of dichloropyridine . It serves as a precursor to the antibiotic enoxacin , [ 2 ] as well as the drug and anpirtoline and the antifungal liranaftate .
The proposed reaction mechanism for the first generation is shown below. [5] [6] The thioester 1 complexes with copper complex 3 to form compound 4.With the oxidative insertion of [Pd] into the carbon–sulfur bond, compound 5 is formed, and with transmetallation, organopalladium species 8 is formed.