- Integrated Synthesis Using Isothiocyanate-Substituted Aryllithiums by Flow Chemistry
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The isothiocyanate (NCS) group is an attractive functional group in the field of organic and pharmaceutical chemistry. It can be transformed into other heteroatomic functional groups. It usually acts as the inductive group of biological activity and has also been traditionally used as the fluorescent-labeling reagent. However, it is not compatible with strong bases. When the NCS group is at para position in halobenzenes, it generally undergoes nucleophilic additions upon reaction with strong bases. To the best of our knowledge, there is currently no general methodology for the formation and reactions of NCS-functionalized aryllithiums for meta and para substituents. Herein, we report the continuous-flow generation of NCS-substituted aryllithiums from the corresponding haloarenes via a selective halogen-lithium exchange reaction and its reaction with various electrophiles to yield NCS-containing products. We also achieved an integrated synthesis through sequential reactions of the NCS-containing compounds with additional nucleophiles using the continuous-flow reactors.
- Lee, Hyune-Jea,Torii, Daiki,Jeon, Yongju,Yoshida, Jun-Ichi,Kim, Heejin
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supporting information
p. 1899 - 1902
(2020/09/11)
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- One-pot three-component tandem reaction: Synthesis of aryl/alkyl cyanamides libraries and their further conversion into tetrazole derivatives
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We have developed methodology for the synthesis of aryl/alkyl cyanamides from amines in one-pot four steps reaction using cheap, readily available and air stable copper source as catalyst under mild reaction conditions. We have also studied the application of cyanamides. In this connection, we could construct aryl tetrazolamine from cyanamides using click reaction.
- Mandapati, Usharani,Mandapati, Pavan,Pinapati, Srinivasarao,Tamminana, Ramana,Rudraraju, Rameshraju
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supporting information
p. 500 - 510
(2018/02/06)
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- Investigation of (Me4N)SCF3 as a Stable, Solid and Safe Reservoir for S=CF2 as a Surrogate for Thiophosgene
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While thiophosgene finds widespread usage on a multi-ton scale, its fluorinated counterpart S=CF2 is essentially unexplored in synthesis. Using experimental reactivity tests, ReactIR and computational techniques, we herein showcase that the solid (Me4N)SCF3 functions as a safe reservoir for S=CF2. A key feature is that the reactive electrophile is not simply released over time, but instead is liberated under activation with a protic nucleophile. The reactivity of S=CF2 is mild, allowing large-scale and late-stage synthetic applications without special reaction control. The mechanism was fully elucidated, including a rationalization of the role of the Me4N cation and the origins of selectivity.
- Scattolin, Thomas,Pu, Maoping,Schoenebeck, Franziska
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supporting information
p. 567 - 571
(2018/01/26)
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- Synthesis of Isothiocyanates and Unsymmetrical Thioureas with the Bench-Stable Solid Reagent (Me4N)SCF3
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A highly efficient, selective, and rapid transformation of primary amines and diamines to isothiocyanates and cyclic thioureas is disclosed. As opposed to established approaches that employ toxic or volatile electrophilic liquids and require reaction control (i.e., slow addition, cooling), this protocol utilizes the bench-stable, solid reagent (Me4N)SCF3 at room temperature. The method is characterized by operational simplicity, high speed, efficiency, high functional group tolerance, and late-stage applicability. The byproducts are solids, allowing isolation of the target compounds by filtration.
- Scattolin, Thomas,Klein, Alexander,Schoenebeck, Franziska
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supporting information
p. 1831 - 1833
(2017/04/11)
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- Copper promoted desulfurization towards the synthesis of isothiocyanates
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The cheap, readily available and air stable catalyst was used as the desulfurization agent for the conversion of aniline to isothiocyanates in one pot two step reaction under mild reaction conditions.
- Mandapati, UshaRani,Pinapati, Srinivasarao,Rudraraju, RameshRaju
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supporting information
p. 125 - 128
(2016/12/26)
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- Structure-activity relationships (SAR) research of thiourea derivatives as dual inhibitors targeting both HIV-1 capsid and human cyclophilin A
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HIV-1 capsid (CA) and human cyclophilin A (CypA) play important roles in HIV-1 assembly and disassembly processes, which are critical in HIV-1 replication. Based on the discovery of thiourea derivatives targeting both of the two proteins and indicating effective inhibitory activities in our group, we designed and synthesized a new class of thiourea derivatives. Their abilities to bind to capsid and cyclophilin A were determined by ultraviolet spectroscopic analysis, fluorescence binding affinity, and PPIase inhibition assay. Furthermore, the newly synthesized compounds were tested for their antiviral activities and cytotoxicities using CEM cells. According to the biological evaluation and subsequent molecular docking analyses, we studied the structure-activity relationships of thiourea derivatives. Three optimal compounds (K17, K24, K25) based on the achieved structure-activity relationships would be the basis for future optimization.
- Chen, Kan,Tan, Zhiwu,He, Meizi,Li, Jiebo,Tang, Shixing,Hewlett, Indira,Yu, Fei,Jin, Yinxue,Yang, Ming
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- INHIBITORS OF BACTERIAL BIOFILM FORMATION
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Organic compounds are described for use in inhibiting or preventing formation of bacterial biofilms.
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Page/Page column 38-39
(2009/12/27)
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- Isothiocyanates from tosyl chloride mediated decomposition of in situ generated dithiocarbamic acid salts
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(Chemical Equation Presented) A facile and general protocol for the preparation of isothiocyanates from alkyl and aryl amines is reported. This method relies on a tosyl chloride mediated decomposition of a dithiocarbamate salt that is generated in situ by treatment of an amine with carbon disulfide and triethylamine. Utilizing this protocol, we have prepared 19-alkyl- and arylisothiocyanates in moderate to excellent yield.
- Wong, Rince,Dolman, Sarah J.
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p. 3969 - 3971
(2008/02/01)
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- Methyl n-aryl-n-formyldithiocarbamates and fluorination thereof
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By reaction of unsubstituted and substituted in the benzene ring formanilides with carbon disulfide and potassium hydroxide in dimethylformamide followed by methylation with methyl iodide were prepared methyl N-aryl-N-formyldithiocarbamates. The reaction of methyl N-4-bromophenyl-N-formyldithiocarbamate with SF4 furnished 4-bromo-N-difluorornethyl-N-trifluoromethylaniline.
- Petko,Yagupol'skii
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p. 1173 - 1177
(2007/10/03)
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