1-hydroxy-1-iodo

SnCl2 reduction produced the 4-hydrazinoisoxazole (243). In ethanol the diazonium salt reacted with the 4-aminoisoxazole to produce the linear triazine (244) (Scheme 85). Diazoisoxazoles can also be treated with KI or H20/urea to produce the 4-iodo or 4-hydroxy derivatives (63AHC(2)365). These Sandmeyer reactions have been extended to a variety of isoxazole systems (77JMC934, 63AHC(2)365). 

Chroman-4-one, 3-hydroxy-2-phenyl-configuration, 3, 631 Chroman-4-one, 2-iodo- H NMR, 3, 583 Chroman-4-one, 2-isopropyl- H NMR, 3, 583 Chroman-4-one, 3-methyl- H NMR, 3, 583 synthesis, 3, 852 Chroman-4-one, 5-methyl-synthesis, 3, 855 Chroman-4-one, 7-methyl-synthesis, 3, 855... 

Imidazole, 1 -hydroxy-2,4,5-triphenyl-3-oxides reactions, S, 455 Imidazole, iodo-nitrodehalogenation, 5, 396-397 Imidazole, 1-iodo-reactions, S, 454 stability, S, 110 Imidazole, 2-iodo-synthesis, S, 401 Imidazole, N-iodo-, S, 393 reactions, 5, 454 Imidazole, 4-iodo-5-methyl-iodination, 5, 400 Imidazole, 2-isopropyl-4-nitro-N-nitration, 5, 351 Imidazole, 2-lithio-reactions, S, 106, 448 Imidazole, 2-mercapto-l-methyl-as antithyroid drug, 1, 171 mass spectra, 5, 358 Imidazole, 1-methoxymethyl-acylation, S, 402 Imidazole, 5-methoxy-l-methyl-reactions... 

Indazole, 5,5-dimethyl-3-trifluoromethyl-4,5-dihydro-trichomonacidal activity, 5, 291 Indazole, 2-ethoxycarbonyl-reactions, 5, 269 Indazole, 3-fluoro-synthesis, S, 263 Indazole, 1-germyl-synthesis, 5, 236 Indazole, 1-glycosyl-synthesis, 5, 289 Indazole, 2-glycosyl-synthesis, 5, 289 Indazole, halo-reactions, S, 266 Indazole, 2-hydroxy-methylation, 5, 269 Indazole, 3-hydroxy-reactions, S, 264 Indazole, 6-hydroxy-diazo coupling, 5, 86 Indazole, hydroxyphenyl-synthesis, S, 288 Indazole, 3-iodo-synthesis, S, 241 Indazole, l-isopropyl-3-phenyl-reduction, 5, 243 Indazole, 3-mercapto-1 -substituted tautomerism, 5, 265 Indazole, methoxy-... 

Indole, 3-hydroxymethyl-2-phenyl-stability, 4, 272 Indole, I-hydroxy-2-phenyl-synthesis, 4, 363 Indole, 2-iodo-synthesis, 4, 216 Indole, 3-iodo-reaetions, 4, 307 synthesis, 4, 216 Indole, 2-iodo-l-methyl-reaetions, 4, 307 Indole, 2-lithio-synthesis, 4, 308 Indole, 3-lithio-synthesis, 4, 308 Indole, 2-mereapto-tautomerism, 4, 38, 199 Indole, 3-mercapto-tautomerism, 4, 38, 199 Indole, 3-methoxy-synthesis, 4, 367 Indole, 5-methoxy-oxidation, 4, 248 Indole, 7-methoxy-2,3-dimethyl-aeetylation, 4, 219 benzoylation, 4, 219 Indole, 5-methoxy-l-methyl-reduetion, 4, 256 Indole, 5-methoxy-l-methyl-3-(2-dimethylaminoethyl)-reaetions... 

Isoxazole, 3-hydroxy-5-phenyl-photolysis, 6, 13 Isoxazole, 5-(o-hydroxyphenyl)-synthesis, 6, 79 Isoxazole, hydroxystyryl-applications, 6, 128 Isoxazole, 4-iodo-... 

Pyrazole, 5-hydroxy-3-methyl-l-phenyl-4-[(o-tolylazo)]-as dyestuff, 5, 299 Pyrazole, 4-iodo-synthesis, 5, 241 Pyrazole, IV-iodo-reactions, 5, 270 synthesis, 5, 234 Pyrazole, 5-mercapto-tautomerism, 5, 265 Pyrazole, methoxy-pharmaceutical activity, 5, 294 reactions... 

Pyrrole, 3-hydroxy-geometry, 4, 158 synthesis, 4, 343 tautomerism, 4, 36, 198 Pyrrole, 3-([Pg.816]

Selenophene, 2,5-dimethyl-3-mercapto-synthesis, 4, 956 tautomerism, 4, 946 Selenophene, 2,4-diphenyl-synthesis, 4, 135 Selenophene, 2,5-diphenyl-lithiation, 4, 949 UV spectra, 4, 941 Selenophene, 2-ethoxycarbonyl-mercuration, 4, 946 Selenophene, halo-reactions, 4, 955 Selenophene, 2-hydroxy-Michael reaction, 4, 953 tautomerism, 4, 36, 945, 953 Selenophene, 3-hydroxy-tautomerism, 4, 36, 945 Selenophene, 3-hydroxy-2,5-dimethyl-tautomerism, 4, 945, 953 Selenophene, 2-hydroxy-5-methyl-methylation, 4, 953 tautomerism, 4, 945 Selenophene, 2-hydroxy-5-methylthio-tautomerism, 4, 945 Selenophene, 3-iodo-synthesis, 4, 955 Selenophene, 3-lithio-reactions, 4, 79 synthesis, 4, 955 Selenophene, 2-mercapto-tautomerism, 4, 38 Selenophene, 3-mercapto-tautomerism, 4, 38 Selenophene, 2-mercapto-5-methyl-synthesis, 4, 956 tautomerism, 4, 946 Selenophene, 3-methoxy-lithiation, 4, 949, 955 synthesis, 4, 955 Selenophene, methyl-oxidation, 4, 951 synthesis, 4, 963 Selenophene, 2-methyl-lithiation, 4, 949 Selenophene, 3-methyl-synthesis, 4, 963... 

Thiazole, 2-( D-galactopentaacetoxypentyl)-4-methyl-synthesis, 6, 295 Thiazole, 2-hydrazi nosynthesis, 6, 297 Thiazole, 2-hydroxy-reactions, 6, 285-286 synthesis, 6, 298, 299 tautomerism, 5, 99 6, 247, 269 Thiazole, 4-hydroxy-reactions, 5, 101 6, 287-288 synthesis, 6, 303 tautomerism, 6, 248, 269 Thiazole, 2-hydroxybenzyl-biosynthesis, 1, 96 Thiazole, 2-hydroxy-4-methyl-arylation, 6, 256 Thiazole, 2-iodo-photolysis, 6, 244 Thiazole, 2-isobutyl-occurrence, 6, 327... 

Thiophene, 2-hydroxy-5-methyl-synthesis, 4, 926 Thiophene, iodo-... 

In 6j5-hydroxy-19-iodo steroids (Figure 12-2) the orientation of the reacting centers O—CH2—I resembles the arrangement in the transition state of an S 2 displacement reaction and consequently the activation energy for the transition (3) (4) is low. It has been suggested that the conformation... 

No systematic study of the minimal required amount of lead tetraacetate has been made. In cases where the product of the hypoiodite reaction is an iodo ether (20-hydroxy steroids) the reaction can be interrupted at the iodohydrin stage by reducing the amount of iodine to about 0.5 mole. For the oxidation of iodo ethers to lactones, chromium trioxide-sulfuric acid in acetone has been used. Silver chromate is often added to the reaction mixture but comparable yields are obtained without the addition of silver salt. 

Reaction of iV-(4-chlorobenzyl)-9-iodo-7-oxo-2,3-dihydro-7//-pyrido [l,2,3- /e]-l,4-benzoxazine-6-carboxamide and HC=CCH20H in the presence of Cu(I)I and (PPh3)2PdCl2 in Et2NH under argon atmosphere for 18h gave 9-(3-hydroxy-l-propynyl) derivative (01MIP2). 

Chloro-, 7-bromo- and 7-iodo derivatives were prepared from 2-cycloalkyl-8-hydroxy-2,3,4,6,11,11 u-hexahydro-1 //-pyrazino[l, 2-6]isoqui-noline-l,4-diones by treatment with NCS and NBS in DMF at 70°C for 24 h, with ICl in diluted HCl at 90 °C for 16h, respectively (98MIP7). 

Viprostol (81) also incorporates a hydroxy group moved to C-16 and protects this from facile metabolic oxidation by vinylation. It is a potent hypotensive and vasodilatory agent both orally and transdermally. The methyl ester moiety is rapidly hydrolyzed in skin and in the liver so it is essentially a prodrug. It is synthesized from protected E-iodo olefin 78 (compare with 75) by conversion to the mixed organocuprate and this added in a 1,4-sense to olefin 79 to produce protected intermediate 80. The synthesis of viprostol concludes by deblocking with acetic acid and then reesterification with diazomethane to give 81 [19]. 

Chromium trioxide, in oxidation of 18-iodo- and 18-hydroxy-18,2O0-oxido-5-pregnene to 18,20-lactone, 46, 59... 

Hydroxy-de-amination 14 Halo(geno)-de-diazoniations 72, 75, 153, 194, 196, 221, 226, 402 f., see also Sandmeyer reaction, Astato-, Bromo-, Chloro-Iodo-de-dedazoniation Hydroxy-de-diazoniation... 

Quinoline-5-sulfonic acid, 8-hydroxy-7-iodo-metal complexes absorptiometry, 1,549 Quinolinium salts in gravimetry, 1, 535 Quinolinol metal complexes color photography, 6,107 8-Quinolinol biological activity, 6, 771 gallium and indium complexes radiopharmacology, 6, 971 radionuclide complexes radiopharmacology, 6,994 8-Quinolyl sulfate hydrolysis metal catalysis, 6,465 Quinones... 

Heteroatom rings, such as that found in quinoline derivatives, can be generated from amino-ketones with [hydroxy(tosyloxy)iodo]benzene and perchloric acid. Cyclic imines are converted to pyridine derivatives with NCS and then excess sodium methoxide. ... 

Alkenes have also been converted to more highly oxidized products. Examples are (1) Treatment with KMn04 in aqueous acetone containing acetic acid gives a-hydroxy ketones. (2) 1,2-Disubstituted and trisubstituted alkenes give a-chloro ketones when oxidized with chromyl chloride in acetone RCH=CR R"—> RCOCCIR R". (3) a-Iodo ketones can be prepared by treating alkenes with... 

CSH7NO 1953-54-4) see Oxitriptan (3P)-3-hydroxy-21-iodo-20,23-dioxo-21-norchol-5-en-24-oic acid etbyl ester... 

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