Five-membered heterocyclic iodine compounds

The five-membered pentavalent iodine heterocycles represent a particularly important class of hypervalent iodine compounds. Cyclic iodine(V) compounds, such as IBX 212 and DMP 213, have found broad practical application as mild and selective reagents for the oxidation of alcohols and some other useful oxidative transformations. Several comprehensive reviews of the chemistry and synthetic applications of IBX and DMP have been published (2011JOC1185, 2006ARK26, 2010T7659, 2011AGE1524, 2001ACE2812). 

Radical reactions of Hoffmann-Loffler-Freytag type with participation of iodine(III) compounds leading to five-member N-heterocycles 97YGK90. 

Thionamides are the most important class of antithyroid compounds in clinical practice used in nondestructive therapy of hyperthyroidism. These agents are potent inhibitors of TPO, which is responsible for the iodination of tyrosine residues of thyroglobulin and the coupling of iodotyrosine residues to form iodothyronines. These drugs have no effect on the iodide pump or on thyroid hormone release. The most clinically useful thionamides are thioureylenes, which are five- or six-membered heterocyclic derivatives of thiourea and include the thiouracil 6-n-propyl-2-thiouracil (PTU) and the thioimidazole 1-methyl-2-mercaptoimidazole (methimazole, Tapazole, MMI). The uptake of these drugs into the thyroid gland is stimulated by TSH and inhibited by iodide. 

A series of heterocyclic compounds containing trivalent iodine, oxygen and boron in a five-membered ring has been prepared by oxidative cyclization of commercially available orf/to-iodophenylboronic acids 182 and 185... 

Several heterocyclic compounds containing trivalent iodine, oxygen, and boron in a five-membered ring have been prepared by oxidative cyclization of the orifco-iodophenylboronic acids 168 and 171 (201IICI1263). 1-Chloro-4-fluoro-lH-lX -benzo[(/][l,2,3]iodoxaborol-3-ol 170 was formed in the reaction of 2-fluoro-6-iodophenylboronic acid 168 with chlorine followed by treatment of the intermediate iododichloride 169 with water. The... 

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