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Pyrithione is the common name of an organosulfur compound with molecular formula C 5 H 5 NOS, chosen as an abbreviation of pyridinethione, and found in the Persian shallot. [4] It exists as a pair of tautomers, the major form being the thione 1-hydroxy-2(1H)-pyridinethione and the minor form being the thiol 2-mercaptopyridine N-oxide; it crystallises in the thione form. [5]
The oxidation of pyridine can be achieved with a number of peracids including peracetic acid and perbenzoic acid. [3] Oxidation can also be effected by a modified Dakin reaction using a urea-hydrogen peroxide complex, [4] and sodium perborate [5] or, using methylrhenium trioxide (CH 3 ReO 3) as catalyst, with sodium percarbonate. [6]
2-Bromopyridine reacts with butyllithium to give 2-lithiopyridine, [2] which is a versatile reagent. [3] Pyrithione can be prepared in a two-step synthesis from 2-bromopyridine by oxidation to the N-oxide with a suitable peracid followed by substitution using either sodium dithionite or sodium sulfide with sodium hydroxide to introduce the thiol functional group.
Pyrithione, the conjugate base of 2-mercaptopyridine-N-oxide, is a fungicide found in some shampoos. Oxidation 2-chloropyridine gives 2-chloropyridine-N-oxide. [ 5 ] The antihistamine pheniramine may be generated via the reaction of phenylacetonitrile with 2-chloropyridine in the presence of a base.
Pyrithione can be prepared in a two-step synthesis from 2-bromopyridine by oxidation to the N-oxide with a suitable peracid followed by substitution using sodium dithionite to introduce the thiol functional group. [12]
Zinc pyrithione (or pyrithione zinc) is a coordination complex of zinc. It has fungistatic (inhibiting the division of fungal cells) and bacteriostatic (inhibiting bacterial cell division) properties and is used in the treatment of seborrhoeic dermatitis [ 2 ] and dandruff .
The Parikh–Doering oxidation is an oxidation reaction that transforms primary and secondary alcohols into aldehydes and ketones, respectively. [1] The procedure uses dimethyl sulfoxide (DMSO) as the oxidant and the solvent, activated by the sulfur trioxide pyridine complex (SO 3 •C 5 H 5 N) in the presence of triethylamine or diisopropylethylamine as base.
Structure of zinc pyrithione, a popular antidandruff medicine. Zinc pyrithione is a coordination complex of a sulfur-substituted pyridine-N-oxide. This zinc complex has useful fungistatic and bacteriostatic properties.. [5]