859205-33-7Relevant academic research and scientific papers
Dearomatization of 3-cyanoindoles by (3 + 2) cycloaddition: From batch to flow chemistry
Chataigner, Isabelle,Gens, Fanny,Legros, Julien,Manneveau, Maxime,Tanii, Saori
supporting information, p. 3481 - 3486 (2020/06/18)
1,3-Dipolar dearomatizing cycloadditions between a non-stabilized azomethine ylide and 3-cyanoindoles or benzofuran afford the corresponding 3D-heterocycles bearing a quaternary carbon centre at the ring junction. While 6 equivalents of ylide precursor 1 are required for full conversion in a classical flask, working under flow conditions limits the excess (3 equiv., tR = 1 min) and leads to a cleaner process, affording cycloadducts that are easier to isolate.
Electron Transfer Photoredox Catalysis: Development of a Photoactivated Reductive Desulfonylation of an Aza-Heteroaromatic Ring
Qiang-Liu,Liu, Yu-Xiu,Song, Hong-Jian,Wang, Qing-Min
supporting information, p. 3110 - 3115 (2020/07/04)
Herein, we report a protocol for desulfonylation of aza-heteroaromatic rings via photoinduced electron transfer and hydrogen atom transfer. This general protocol has a wide substrate range and moderate to good yields. The utility of the method was demonstrated by the chemoselective desulfonylation of a molecule containing both an aliphatic and an aromatic sulfonamide. (Figure presented.).
A Transition-Metal-Free One-Pot Cascade Process for Transformation of Primary Alcohols (RCH2OH) to Nitriles (RCN) Mediated by SO2F2
Jiang, Ying,Sun, Bing,Fang, Wan-Yin,Qin, Hua-Li
, p. 3190 - 3194 (2019/05/21)
A new transition-metal-free one-pot cascade process for the direct conversion of alcohols to nitriles was developed without introducing an “additional carbon atom”. This protocol allows transformations of readily available, inexpensive, and abundant alcohols to highly valuable nitriles.
Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO
Fang, Wan-Yin,Qin, Hua-Li
, p. 5803 - 5812 (2019/05/14)
A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.
Marine-Natural-Product Development: First Discovery of Nortopsentin Alkaloids as Novel Antiviral, Anti-phytopathogenic-Fungus, and Insecticidal Agents
Ji, Xiaofei,Guo, Jincheng,Liu, Yuxiu,Lu, Aidang,Wang, Ziwen,Li, Yongqiang,Yang, Shaoxiang,Wang, Qingmin
, p. 4062 - 4072 (2018/05/03)
Nortopsentin alkaloids were found to have potent antiviral, anti-phytopathogenic-fungus, and insecticidal activities for the first time. Antiviral-activity tests revealed that these compounds were very sensitive to substituents, so a series of nortopsentin derivatives were designed, synthesized, and systematically evaluated for their antiviral activities against TMV, their fungicidal activities, and their insecticidal activities on the basis of a structural-diversity-derivation strategy. Compounds 2e (in vivo inactivation-, curative-, and protective-activity inhibitory rates of 50, 59, and 56%, respectively, at 500 μg/mL) and 2k (in vivo inactivation-, curative-, and protective-activity inhibitory rates of 60, 58, and 52%, respectively, at 500 μg/mL), with excellent antiviral activities and good physicochemical properties, emerged as new lead compounds for novel-antiviral-agent development. Further fungicidal-activity tests revealed that these alkaloids displayed broad-spectrum fungicidal activities. Compounds 2f, 2h, and 2j emerged as new lead compounds for antifungal-activity research. Additionally, all the compounds displayed good insecticidal activities against five kinds of insects, including Mythimna separate, Helicoverpa armigera, Ostrinia nubilalis, Plutella xylostella, and Culex pipiens pallens.
CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides via Cu-vinylidene intermediates
Liao, Zhen-Yuan,Liao, Pen-Yuan,Chien, Tun-Cheng
, p. 14404 - 14407 (2016/12/23)
CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides was initiated by the formation of Cu-acetylide to trigger N-CN bond cleavage of the N-sulfonylcyanamide moiety followed by CN migration to form a β-cyano Cu-vinylidene intermediate. Subsequently, the indole ring closure furnished the corresponding 1-sulfonyl-3-cyanoindoles.
Simple one-pot conversion of alcohols into nitriles
Shimojo, Hiroyuki,Moriyama, Katsuhiko,Togo, Hideo
, p. 2155 - 2164 (2013/08/23)
Various benzylic and primary alcohols were efficiently converted into the corresponding nitriles in good yields at room temperature by treatment with tert-butyl hypochlorite, diiodine, or 1,3-diiodo-5,5-dimethylhydantoin in the presence of (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl (TEMPO), followed by treatment with diiodine and aqueous ammonia. The nitriles were obtained in good yields and high purities simply by extraction of the reaction mixture with chloroform and subsequent removal of the solvent.
Practical synthesis of aromatic nitriles via gallium-catalysed electrophilic cyanation of aromatic C-H bonds
Okamoto, Kazuhiro,Watanabe, Masahito,Murai, Masahito,Hatano, Ryo,Ohe, Kouichi
supporting information; experimental part, p. 3127 - 3129 (2012/04/23)
A gallium-catalysed, direct cyanation reaction of aromatic and heteroaromatic C-H bonds with cyanogen bromide was developed as a practical synthetic method for the preparation of aromatic nitriles. The Royal Society of Chemistry 2012.
Direct oxidative conversion of alkyl halides into nitriles with molecular iodine and 1,3-diiodo-5,5-dimethylhydantoin in aq ammonia
Iida, Shinpei,Ohmura, Ryosuke,Togo, Hideo
experimental part, p. 6257 - 6262 (2011/03/20)
Various benzylic halides were smoothly and directly converted into the corresponding aromatic nitriles in high yields using molecular iodine and 1,3-diiodo-5,5-dimethylhydantoin, respectively, in aq ammonia. Similarly, primary alkyl halides were also converted into corresponding nitriles in moderate to good yields using molecular iodine and 1,3-diiodo-5,5-dimethylhydantoin in aq ammonia, although a long reaction time was required. The present reaction is a new method for the preparation of aromatic nitriles from benzylic halides and a new method for the conversion of alkyl halides into corresponding nitriles with retention of the number of carbon atoms.
A simple synthesis of nitriles from aldoximes
Singh, Manish K.,Lakshman, Mahesh K.
experimental part, p. 3079 - 3084 (2009/08/08)
Easily synthesized aldoximes have been converted to the corresponding nitriles under very mild conditions by a simple reaction with lH-benzotriazol-l-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) and DBU in CH2CI2, THF, or DMF. As an alternative reagent that eliminates the formation of hexamethylphosphoramide as a byproduct, use of lH-benzotriazol-lyl-4-methylbenzenesulfonate (Bt-OTs) and DBU was investigated. Reactions with this reagent also proceeded smoothly and in good yields, although in one case N-sulfonylation was observed. An attempt to gain mechanistic insight into the BOP-mediated reaction has been made using 31P{ 1H} NMR. However, no phosphorus-bearing intermediate could be readily observed. Finally, the method has been applied to the synthesis of an antiviral 4'-cyano adenosine analogue from a commercial precursor using a single saccharide protecting group.
