Iodine In Synthesis Research Articles

Iodine(I) and Silver(I) Complexes of Benzoimidazole and Pyridylcarbazole Derivatives.

The synthesis of iodine(I) complexes with either benzoimidazole or carbazole-derived sp2 N-containing Lewis bases is described, as well as their corresponding silver(I) complexes. The addition of elemental iodine to the linear two-coordinate Ag(I) complexes produces iodine(I) complexes with a three-center four-electron (3c-4e) [N-I-N]+ bond. The 1 H and 1 H-15 N HMBC NMR studies unambiguously confirm the formation of the complexes in all cases via the [N-Ag-N]+ →[N-I-N]+ cation exchange, with the 15 N NMR chemical shift change between 94 to 111 ppm when compared to the free ligand. The single crystal X-ray crystallographic studies on eight I+ complexes revealed highly symmetrical [N-I-N]+ bonds with I-N bond distances of 2.21-2.26 Å and N-I-N angles of 177-180°, whilst some of the corresponding Ag+ complexes showed a clear deviation from linearity with N-Ag-N angles of ca. 150° and Ag-N bond distances of 2.09-2.18 Å.

Change of iodine load and thyroid homeostasis induced by ammonium perchlorate in rats.

Ammonium perchlorate (AP), mainly used as solid propellants, was reported to interfere with homeostasis via competitive inhibition of iodide uptake. However, detailed mechanisms remain to be elucidated. In this study, AP was administered at 0, 130, 260 and 520 mg/kg every day to 24 male SD rats for 13 weeks. The concentrations of iodine in urine, serum thyroid hormones levels, total iodine, relative iodine and total protein, and malondialdehyde (MDA), superoxide dismutase (SOD) and catalase (CAT) activity in thyroid tissues were measured, respectively. Our results showed that high-dose perchlorate induced a significant increase in urinary iodine and serum thyroid stimulating hormone (TSH), with a decrease of total iodine and relative iodine content. Meanwhile, free thyroxine (FT4) was decreased and CAT activity was remarkably increased. Particularly, the CAT activity was increased in a dose-dependent manner. These results suggested that CAT might be enhanced to promote the synthesis of iodine, resulting in elevated urinary iodine level. Furthermore, these findings suggested that iodine in the urine and CAT activity in the thyroid might be used as biomarkers for exposure to AP, associated with thyroid hormone indicators such as TSH, FT4.

ChemInform Abstract: Hypervalent Iodine in Synthesis. Part 32. A Novel Way for the Synthesis of N-Sulfonylsulfilimines from Sulfides and Sulfonamides Using Iodosobenzene Diacetate.

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ChemInform Abstract: Hypervalent Iodine in Synthesis. Part 44. Stereoselective Synthesis of Vinylic Selenides by the Reaction of Sodium Selenolates with Vinyl(phenyl)iodonium Salts.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Hypervalent Iodine in Synthesis. Part 53. Synthesis of 2,4-Disubstituted and 2,4,5-Trisubstituted 1,3-Selenazoles.

ChemInform Abstract: Hypervalent Iodine in Synthesis. Part 53. Synthesis of 2,4-Disubstituted and 2,4,5-Trisubstituted 1,3-Selenazoles.

Hypervalent Iodine in Synthesis: A Novel Two‐Step Procedure for the Synthesis of New Derivatives of 1H‐Imidazo[1,2‐b]pyrazole by the Cyclocondensation Between 5‐Amino‐4‐cyano‐3‐phenyl‐1H‐pyrazole and α‐Tosyloxyacetophenones or α‐Haloacetophenones.

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Hypervalent Iodine in Synthesis. Part 86. Selective Copper‐Catalyzed N‐Monoarylation and N1,N3‐Diarylation of Uracil and Its Derivatives with Diaryliodonium Salts.

Hypervalent Iodine in Synthesis. Part 86. Selective Copper‐Catalyzed N‐Monoarylation and N¹,N³‐Diarylation of Uracil and Its Derivatives with Diaryliodonium Salts.

Hypervalent Iodine in Synthesis: A Novel Two‐Step Procedure for the Synthesis of New Derivatives of 1H‐Imidazo[1,2‐b]‐pyrazole by the Cyclocondensation Between 5‐Amino‐4‐cyano‐3‐phenyl‐1H‐pyrazole and α‐Tosyloxyacetophenones or α‐Haloacetophenones

A series of new 7‐cyano‐6‐phenyl‐2‐aryl‐1H‐imidazo[1,2‐b]pyrazoles (5) by the cyclocondensation reactions between 5‐amino‐4‐cyano‐3‐phenyl‐1H‐pyrazole (1) and α‐bromoacetophenones (3) or α‐tosyloxyacetophenones (2) obtained by the reactions of acetophenones with [hydroxy(tosyloxy)iodo]benzene (HTIB) have been synthesized in good yields, and the intermediates 5‐amino‐4‐cyano‐6‐phenyl‐1‐(aroylmethyl)pyrazoles (4) were isolated as a potent evidence for the regioselectivity. The syntheses of 4 and 5 have been achieved successfully through the procedure involving α‐tosyloxyacetophenones and some through the procedure involving α‐bromoacetophenones. When utilizing α‐tosyloxyacetophenones, the reactions were more eco‐friendly, the reaction time was significantly reduced, and the synthetic procedure was more convenient and easier to manipulate.

Graphical Abstracts

Synth. Commun. 2005, 35, 493 Hypervalent Iodine in Synthesis: A Novel Two‐Step Procedure for the Synthesis of New Derivatives of 1H‐Imidazo[1,2‐b]pyrazole by the Cyclocondensation between 5‐Amino‐4‐cyano‐3‐phenyl‐1H‐pyrazole and α ‐Tosyloxyacetophenones or α‐Haloacetophenones Li Ming1, 2, Zhao Guilong1, Wen Lirong1, and Yang Huazheng2 1College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. China 2Institute of Elemento‐Organic Chemistry, Nankai University, Tianjin, P. R. China A facile procedure for the synthesis of 1H‐Imidazo[1,2‐b]pyrazole framework using a hypervalent iodine compound.

Hypervalent Iodine in Synthesis. Part 87. The Synthesis of 2,5‐Diaryl‐2H‐tetrazoles.

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Hypervalent iodine in synthesis 87: The synthesis of 2,5-diaryl-2H-tetrazoles

In the presence of cuprous iodide and potassium carbonate, N-arylation of 5-aryl-2H-tetrazole with a diaryliodonium salt proceeds smoothly in DMF at room temperature to give 2, 5-diaryl-2H-tetrazoles in moderate to good yield.

Hypervalent Iodine in Synthesis. Part 94. A Facile Synthesis of 2‐Substituted‐imidazo[1,2‐a]pyridines by Cyclocondensation of Alkynyl(phenyl)iodonium Salts and 2‐Aminopyridine.

Hypervalent Iodine in Synthesis. Part 94. A Facile Synthesis of 2‐Substituted‐imidazo[1,2‐a]pyridines by Cyclocondensation of Alkynyl(phenyl)iodonium Salts and 2‐Aminopyridine.

Hypervalent Iodine in Synthesis. Part 74. Synthesis and Reactivity of New Functionalized Alkenyliodonium Salts.

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Hypervalent Iodine in Synthesis. 94. A Facile Synthesis of 2-Substituted-imidazo[1,2-a]pyridines by Cyclocondensation of Alkynyl(phenyl) iodonium Salts and 2-Aminopyridine

A facile method for the synthesis of 2-substituted-imidazo[1,2-a]pyridines is achieved by cyclocondensation of alkynyl(phenyl)iodonium salts with 2-aminopyridine.

Hypervalent Iodine in Synthesis. Part 90. A Mild and Efficient Method for the Iodination of Pyrazoles.

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Hypervalent iodine in synthesis 93. A facile synthesis of 2‐substituted imidazo[1,2‐a]pyrimidines by cyclocondensation of alkynyl(phenyl)iodonium salts and 2‐aminopyrimidine

AbstractSimple stirring of a mixture of the alkynyl(phenyl)iodonium salts 1 with 2‐aminopyrimidine 2 in chloroform under reflux for two hours in the presence of K2CO3 gave, after workup, the 2‐substituted imidazo[1,2‐α]pyrimidines 3 in moderate to good yields. A possible mechanism for the formation of 3 involves the intramolecular cyclization of the intermediate alkylidenecarbene 6.

Hypervalent Iodine in Synthesis. Part 91. A Mild and Efficient Method for the Halogenation of 6‐Methyluracil Derivatives.

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Hypervalent Iodine in Synthesis. Part 83. Palladium‐Catalyzed Carbonylative Coupling of Diaryliodonium Salts Mediated by Indium.

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Hypervalent Iodine in Synthesis. Part 85. An Efficient Method for the Synthesis of N‐Arylbenzimidazoles by the Copper‐Catalyzed N‐Arylation of Benzimidazole with Diaryliodonium Salts.

Hypervalent Iodine in Synthesis. Part 85. An Efficient Method for the Synthesis of N‐Arylbenzimidazoles by the Copper‐Catalyzed N‐Arylation of Benzimidazole with Diaryliodonium Salts.

Hypervalent Iodine in Synthesis. Part 73: A New Stereoselective Synthesis of 1‐(1‐Alkenyl) Benzotriazoles by the Reaction of Alkenyl(phenyl)iodonium Salts with Benzotriazole.

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