http://www.mdpi.com/journal/molecules/special_issues/organic-iodine/ Dear Colleagues, In recent years, a large number of organic reactions have been investigated using molecule iodine-catalyzed and iodine-induced methods. Therefore, many new compounds have been synthesized using molecular iodine. Iodine is an inexpensive weak Lewis acid, non-toxic, and readily available reagent for various organic transformations and yields products with outstanding selectivity with minimum by products. In view of the increasingly expanding field of molecular iodine-mediated reactions and significant attention in this area from academic and industrial scientists, we believe a respectable journal should publish a whole issue on iodine mediated reactions toward the synthesis of important organic compounds under environmentally benign conditions. I am delighted that Molecules have come forward and ask me to take over this responsibility. The main objective of this issue will be to provide useful information to researchers and students who are interested in the chemistry of iodine and its fascinating role in organic synthesis. Efforts will be made to include not only the synthesis of organic compounds but also to understand the mechanism of iodine-mediated reactions in different solvents including in water. In summary, I have no doubt that this volume in Molecules will be extremely valuable resource for many groups who are working on organoiodine chemistry. Prof. Dr. Bimal K. Banik Hideo Togo, Ph. D. Guest Editors Submission All papers should be submitted to molecules@mdpi.com with copy to the guest editor. To be published continuously until the deadline and papers will be listed together at the special websites. Submitted papers should not have been previously published nor be currently under consideration for publication elsewhere. All papers are refereed through a peer review process. A guide for authors, sample copies and other relevant information for submitting papers are available on the Instructions for Authors page. Molecules is an international peer-reviewed monthly journal published by MDPI. Please visit the Instructions for Authors page before submitting a paper. Open Access publication fees are 800 CHF per paper. English correction fees (250 CHF) will be added in certain cases (1050 CHF per paper for those papers that require extensive additional formatting and/or English corrections.). http://www.mdpi.com/1420-3049/15/6/4207/ A microwave-induced iodine-catalyzed simple, rapid and convenient synthesis of different types of quinoxalines via condensation of 1,2-diamines with 1,2-dicarbonyl compounds has been accomplished with an excellent yield. http://www.mdpi.com/1420-3049/15/6/4207/ Wed, 09 Jun 2010 00:00:00 CEST Molecules 2010-06-09 15 6 Communication 4207 4212 1420-3049 An Effective Microwave-Induced Iodine-Catalyzed Method for the Synthesis of Quinoxalines via Condensation of 1,2-Diamines with 1,2-Dicarbonyl Compounds 2010-06-09 doi: 10.3390/molecules15064207 Bandyopadhyay Mukherjee Rodriguez Banik http://www.mdpi.com/1420-3049/15/5/3211/ Cyclodehydration of Bohlmann-Rahtz aminodienone intermediates using N-iodosuccinimide as a Lewis acid proceeds at low temperature under very mild conditions to give the corresponding 2,3,6-trisubstituted pyridines in high yield and with total regiocontrol. http://www.mdpi.com/1420-3049/15/5/3211/ Fri, 30 Apr 2010 00:00:00 CEST Molecules 2010-04-30 15 5 Article 3211 3227 1420-3049 Bohlmann-Rahtz Cyclodehydration of Aminodienones to Pyridines Using N-Iodosuccinimide 2010-04-30 doi: 10.3390/molecules15053211 Bagley Glover http://www.mdpi.com/1420-3049/15/4/2857/ Oxidative chlorination with HCl/H2O2 in 1,1,1-trifluoroethanol was used to transform aryl iodides into aryliodine(III) dihalides. In this instance 1,1,1-trifluoroethanol is not only the reaction medium, but is also an activator of hydrogen peroxide for the oxidation of hydrochloric acid to molecular chlorine. Aryliodine(III) dichlorides were formed in 72–91% isolated yields in the reaction of aryl iodides with 30% aqueous hydrogen peroxide and hydrochloric acid at ambient temperature. A study of the effect that substituents on the aromatic ring have on the formation and stability of aryliodine(III) dichlorides shows that the transformation is easier to achieve in the presence of the electron-donating groups (i.e. methoxy), but in this case the products rapidly decompose under the reported reaction conditions to form chlorinated arenes. The results suggest that oxidation of hydrogen chloride with hydrogen peroxide is the initial reaction step, while direct oxidation of aryl iodide with hydrogen peroxide is less likely to occur. http://www.mdpi.com/1420-3049/15/4/2857/ Tue, 20 Apr 2010 00:00:00 CEST Molecules 2010-04-20 15 4 Article 2857 2871 1420-3049 Conversion of Aryl Iodides into Aryliodine(III) Dichlorides by an Oxidative Halogenation Strategy Using 30% Aqueous Hydrogen Peroxide in Fluorinated Alcohol 2010-04-20 doi: 10.3390/molecules15042857 Podgoršek Iskra http://www.mdpi.com/1420-3049/15/4/2686/ The use of radiopharmaceuticals for molecular imaging of biochemical and physiological processes in vivo has evolved into an important diagnostic tool in modern nuclear medicine and medical research. Positron emission tomography (PET) is currently the most sophisticated molecular imaging methodology, mainly due to the unrivalled high sensitivity which allows for the studying of biochemistry in vivo on the molecular level. The most frequently used radionuclides for PET have relatively short half-lives (e.g. 11C: 20.4 min; 18F: 109.8 min) which may limit both the synthesis procedures and the time frame of PET studies. Iodine-124 (124I, t1/2 = 4.2 d) is an alternative long-lived PET radionuclide attracting increasing interest for long term clinical and small animal PET studies. The present review gives a survey on the use of 124I as promising PET radionuclide for molecular imaging. The first part describes the production of 124I. The second part covers basic radiochemistry with 124I focused on the synthesis of 124I-labeled compounds for molecular imaging purposes. The review concludes with a summary and an outlook on the future prospective of using the long-lived positron emitter 124I in the field of organic PET chemistry and molecular imaging. http://www.mdpi.com/1420-3049/15/4/2686/ Tue, 13 Apr 2010 00:00:00 CEST Molecules 2010-04-13 15 4 Review 2686 2718 1420-3049 Iodine-124: A Promising Positron Emitter for Organic PET Chemistry 2010-04-13 doi: 10.3390/molecules15042686 Koehler Gagnon McQuarrie Wuest http://www.mdpi.com/1420-3049/15/4/2520/ An expeditious synthesis of N-substituted pyrroles has been developed by reacting 2,5-dimethoxy tetrahydrofuran and several amines using a microwave-induced molecular iodine-catalyzed reaction under solventless conditions. http://www.mdpi.com/1420-3049/15/4/2520/ Fri, 09 Apr 2010 00:00:00 CEST Molecules 2010-04-09 15 4 Communication 2520 2525 1420-3049 An Expeditious Synthesis of N-substituted Pyrroles via Microwave-Induced Iodine-Catalyzed Reactions under Solventless Conditions 2010-04-09 doi: 10.3390/molecules15042520 Bandyopadhyay Mukherjee Banik http://www.mdpi.com/1420-3049/15/3/1340/ A novel method for the conversion of unprotected and unmodified aldoses to aldo-imidazoles has been developed. Using iodine as a catalyst in acetic acid solution, a series of mono- and oligosaccharides, including those containing carboxyl and acetamido groups, undergo an oxidative condensation reaction with aromatic vicinal diamines at room temperature to give the corresponding aldo-imidazole products in high yields. No cleavage of the glycosidic bond occurs under the mild reaction conditions. The compositional analysis of saccharides is commonly realized by capillary electropheresis of the corresponding aldo-imidazole derivatives, which are easily synthesized by the reported iodine-promoted oxidative condensation. In addition, a series of aldo-imidazoles were determined by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI–TOF MS) to analyze molecular weight and ion intensity. The diamine-labeled saccharides showed enhanced signals in MALDI–TOF MS. The combined use of aldoimidazole derivatization and mass spectrometric analysis thus provides a rapid method for identification of saccharides, even when less than 1 pmol of saccharide is present in the sample. These results can be further applied to facilitate the isolation and analysis of novel saccharides. http://www.mdpi.com/1420-3049/15/3/1340/ Fri, 05 Mar 2010 00:00:00 CET Molecules 2010-03-05 15 3 Article 1340 1353 1420-3049 I2-Catalyzed Oxidative Condensation of Aldoses with Diamines: Synthesis of Aldo-Naphthimidazoles for Carbohydrate Analysis 2010-03-05 doi: 10.3390/molecules15031340 Chunchi Lin Wei-Ting Hung Chien-Yuan Kuo Kuo-Shiang Liao Yin-Chen Liu Wen-Bin Yang http://www.mdpi.com/1420-3049/15/2/1082/ Because of their interesting biological properties various methods for the synthesis of substituted pyrroles are described in the literature. However, synthesis of pyrroles fused with a β-lactam ring has not been reported. Our group has demonstrated synthesis and biological evaluation of various β-lactams as anticancer agents. The anticancer activities of these compounds have prompted us to study the synthesis of pyrroles bound to the β-lactams. We have identified an expeditious synthetic method for the preparation of pyrroles fused with β-lactams by reacting 3-amino β-lactams with acetonylacetone in the presence of catalytic amounts (5 mol%) of molecular iodine at room temperature. It has also been discovered that the reaction gives products under domestic and automated microwave oven irradiation. To our knowledge, there are no other prior reports that describe the synthesis of pyrrole-substituted β-lactams. http://www.mdpi.com/1420-3049/15/2/1082/ Tue, 23 Feb 2010 00:00:00 CET Molecules 2010-02-23 15 2 Communication 1082 1088 1420-3049 Remarkable Iodine-Catalyzed Synthesis of Novel Pyrrole- Bearing N-Polyaromatic β-Lactams 2010-02-23 doi: 10.3390/molecules15021082 Debasish Bandyopadhyay Gildardo Rivera Isabel Salinas Hector Aguilar Bimal K. Banik http://www.mdpi.com/1420-3049/14/12/5308/ Prompted by the scant attention paid by published literature reviews to the applications of molecular iodine in oxidative aromatization reactions, we decided to review methods developed to-date involving iodine as an oxidant to promote aromatization of α,β-unsaturated cyclic compounds. http://www.mdpi.com/1420-3049/14/12/5308/ Wed, 16 Dec 2009 00:00:00 CET Molecules 2009-12-16 14 12 Review 5308 5322 1420-3049 Molecular Iodine—An Expedient Reagent for Oxidative Aromatization Reactions of α,β-Unsaturated Cyclic Compounds 2009-12-16 doi: 10.3390/molecules14125308 Malose Jack Mphahlele http://www.mdpi.com/1420-3049/14/12/4814/ Molecular iodine has established itself as a readily available and easy-to-handle electrophilic and oxidizing reagent used in various organic transformations. In this review attention is focused on the use of molecular iodine in promoting cyclization (iodocyclization and cyclodehydroiodination) of tethered heteroatom-containing alkenyl or alkynyl systems. http://www.mdpi.com/1420-3049/14/12/4814/ Wed, 25 Nov 2009 00:00:00 CET Molecules 2009-11-25 14 12 Review 4814 4837 1420-3049 Molecular Iodine-Mediated Cyclization of Tethered Heteroatom-Containing Alkenyl or Alkynyl Systems 2009-11-25 doi: 10.3390/molecules14124814 Malose Jack Mphahlele http://www.mdpi.com/1420-3049/14/11/4669/ Piceatannol (E-3,5,3’,4’-tetrahydroxystilbene) is a phytoalexin synthesized in grapes in response to stress conditions. It exhibits strong antioxidant and antileukaemic activities due to the presence of the catechol moiety. To modify some physical properties like solubility, and miscibility in non-aqueous media some new previously unreported piceatannol derivatives having lipophilic chains on the A-ring were prepared in good yields by a simple and efficient procedure. The key step was a chemo- and regioselective aromatic hydroxylation with 2-iodoxybenzoic acid (IBX). The new compounds showed antioxidant activity and seemed promising for possible applications as multifunctional emulsifiers in food, cosmetic and pharmaceutical fields. http://www.mdpi.com/1420-3049/14/11/4669/ Tue, 17 Nov 2009 00:00:00 CET Molecules 2009-11-17 14 11 Article 4669 4681 1420-3049 New Lipophilic Piceatannol Derivatives Exhibiting Antioxidant Activity Prepared by Aromatic Hydroxylation with 2-Iodoxybenzoic Acid (IBX) 2009-11-17 doi: 10.3390/molecules14114669 Roberta Bernini Maurizio Barontini Carmela Spatafora http://www.mdpi.com/1420-3049/14/9/3132/ Iodoarylation of arylacetylenes was performed using a simple reagent system composed of molecular iodine and [bis(benzoyloxy)iodo]benzene. Most arylacetylenes efficiently underwent the iodoarylation reaction with electron-rich arenes to give trans 1,1-diaryl-2-iodoethene adducts regio- and stereoselectively. As an exception, the iodoarylation of p-methoxyphenylacetylene resulted in a mixture of E- and Z-isomers of the corresponding product. http://www.mdpi.com/1420-3049/14/9/3132/ Mon, 24 Aug 2009 00:00:00 CEST Molecules 2009-08-24 14 9 Article 3132 3141 1420-3049 Iodoarylation of Arylalkynes with Molecular Iodine in the Presence of Hypervalent Iodine Reagents 2009-08-24 doi: 10.3390/molecules14093132 Md. Ataur Rahman Tsugio Kitamura