cas 2740-81-0, 2-CHLOROPHENYL ISOTHIOCYANATE

Articles about 2740-81-0Total 45 be found

Article title
Article abstract
Author
Journal number and time
Download

COMPOUNDS WITH COPPER- OR ZINC-ACTIVATED TOXICITY AGAINST MICROBIAL INFECTION
Heterocyclic compounds with a novel pyrazole thioamide-based NNSN structural motif, having highly effective zinc- or copper-activated toxicity against microbial infections at micromolar or nanomolar minimum inhibitory concentrations (MIC), and methods of making and using same.
-
(2022/02/05)

Microwave mediated synthesis of 2-aminooxazoles
A microwave mediated synthesis of 2-aminooxazoles at 150 °C was developed, providing products with a variety of functional groups. The reaction takes 5 min and provides product with a simple precipitation at moderate to good yields without the need for recrystallization or flash chromatography.
Klug, Trevan,Cronin, Adam,O'Brien, Eli,Schioldager, Ryan,Johnson, Hunter,Gleason, Cameron,Schmid, Connor,Soderberg, Nathan,Manjunath, Aashrita,Liyanage, Duminda,Lazaro, Horacio,Kimball, Joshua J.,Eagon, Scott
supporting information

(2021/12/14)

Design, synthesis and biological evaluation of novel 2,4-disubstituted quinazoline derivatives targeting H1975 cells via EGFR-PI3K signaling pathway
In order to find new and highly effective anti-tumor drugs with targeted therapeutic effects, a series of novel 4-aminoquinazoline derivatives containing N-phenylacetamide structure were designed, synthesized and evaluated for antitumor activity against four human cancer cell lines (H1975, PC-3, MDA-MB-231 and MGC-803) using MTT assay. The results showed that the compound 19e had the most potent antiproliferative activity against H1975, PC-3, MDA-MB-231 and MGC-803 cell lines. At the same time, compound 19e could significantly inhibit the colony formation and migration of H1975 cells. Compound 19e also arrested the H1975 cell cycle in the G1 phase and mediated cell apoptosis, promoted the accumulation of ROS in H1975 cells. Furthermore, compound 19e exerted antitumor effect in vitro by reducing the expression of anti-apoptotic protein Bcl-2 and increasing the pro-apoptotic protein Bax and p53. Mechanistically, compound 19e could significantly decreased the phosphorylation of EGFR and its downstream protein PI3K in H1975 cells. Which indicated that compound 19e targeted H1975 cell via interfering with EGFR-PI3K signaling pathway. Molecular docking showed that compound 19e could bind into the active pocket of EGFR. Those work suggested that compound 19e would have remarkable implications for further design of anti-tumor agents.
Chao, Gao,Dai, Honglin,Ke, Yu,Li, Erdong,Lihong, Shan,Liu, Hongmin,Liu, Limin,Si, Xiaojie,Wang, Zhengjie,Yang, Zhang,Zhang, Luye,Zhang, Qiurong,Zheng, Jiaxin
(2021/07/28)

NaOH-promoted one-pot aryl isothiocyanate synthesis under mild benchtop conditions
In this work, we have established a green synthesis of aryl isothiocyanates promoted by the low-cost and readily available NaOH from aryl amines and carbon disulfide in a one-pot procedure. The developed protocol features no extra desulfurating reagents and mild benchtop conditions, in which NaOH serves as both the base and the desulfurating reagent to decompose the dithiocarbamate intermediate. Fourteen examples of aryl amines bearing electronic neutral, rich and poor substituents, as well as benzylamine, have proved to be compatible substrates in the developed method to furnish the corresponding isothiocyanates. The reaction has been performed on a gram scale to further demonstrate its synthetic utility. Compared to the reported base-promoted synthesis of aryl isothiocyanates that requires the use of special equipment, such as the ball mill or the microwave reactor, the simplicity in operation and scalability enables this method to efficiently access a variety of aryl isothiocyanates.
Li, Hang,Liu, Xinyun,Yin, Xiaogang
supporting information
p. 839 - 844
(2021/05/27)

A catalyst-free method for the synthesis of 1,4,2-dithiazoles from isothiocyanates and hydroxylamine triflic acid salts
A catalyst-free method for the preparation of 1,4,2-dithiazoles is developed by reactions of isothiocyanates with hydroxylamine triflic acid salts. This reaction achieves C-S, C-N, and S-N bond formation, and a range of products are obtained in moderate to good yields. The obvious feature is using shelf-stable hydroxylamine triflic acid salts as a N source to synthesize heterocycles under mild conditions.
An, Zhenyu,Liu, Yafeng,Ren, Yi,Wang, Ting,Yan, Rulong
supporting information
p. 6206 - 6209
(2021/07/28)

Design, synthesis, and biological evaluation of novel substituted thiourea derivatives as potential anticancer agents for NSCLC by blocking K-Ras protein-effectors interactions
Mutation of the proto-oncogene K-Ras is one of the most common molecular mechanisms in non-small cell lung cancer. Many drugs for treating lung cancer have been developed, however, due to clinical observed K-Ras mutations, corresponding chemotherapy and targeted therapy for such mutation are not efficient enough. In this study, on the basis of the crystal structure of K-Ras, 21 analogues (TKR01–TKR21) containing urea or thiourea were rationally designed, which can effectively inhibit the lung cancer cell A549 growth. The designing of these compounds was based on the structure of K-Ras protein, and the related groups were replaced by bioisosteres to improve the affinity and selectivity. Biological testing revealed that compound TKR15 could significantly inhibit the proliferation of A549 cell with IC50 of 0.21 μM. Docking analysis showed that the TKR15 can effectively bind to the hydrophobic cavity and form a hydrogen bond with the Glu37. In addition, through flow apoptosis assay and immunofluorescence staining assay, it confirmed that this compound can inhibit A549 cell proliferation with the mechanism of blocking K-RasG12V protein and effector proteins interactions through the apoptotic pathway. In conclusion, our studies in finding novel potent compound (TKR15) with confirmed mechanism showed great potential for further optimisation and other medicinal chemistry relevant studies.
Cheng, Minghui,Meng, Xin,Tang, Haikang,Xu, Wenqing,Yang, Fujun,Zhang, Yuan
p. 344 - 353
(2019/12/30)

Synthesis and antitumor activity of novel pyridazinone derivatives containing 1,3,4-thiadiazole moiety
A series of novel pyridazinone derivatives containing the 1,3,4-thiadiazole moiety were synthesized and characterized by 1H NMR, 13C NMR, spectroscopies HRMS and IR. Among them, the structure of compound 5c (2-(Tert-butyl)?4-chloro-5-((5-((2-ethylphenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One) was unambiguously confirmed via single crystal X-ray diffraction analysis. The inhibitory activity of all the target compounds against MGC-803 and Bcap-37 was determined by MTT assay, with doxorubicin (the inhibition rates were 95.5 ± 0.4% and 95.7 ± 1.0% respectively) as a control. The preliminary results showed that the inhibitory activity of compound 5n (2-(Tert-butyl)?4-chloro-5-((5-((3-fluorophenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One) was superior to the others. The inhibition rates of MGC-803 and Bcap-37 cells were 86.3 ± 2.2% and 92.3 ± 0.6% at a concentration of 10 μmol/L, respectively. The preliminary structure-activity relationship showed that when the 2-position of the benzene ring was substituted by a methyl group, such as compound 5j (2-(Tert-butyl)?4-chloro-5-((5-((2,3-dimethylphenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One), it exhibited good anticancer activity on MGC-803 cells. Besides, introducing fluorine, chlorine, or trifluoromethyl group onto the benzene ring, such as compound 5 m (2-(Tert-butyl)?4-chloro-5-((5-((4-(trifluoromethoxy)phenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One), displayed good anticancer activity on MGC-803 and Bcap-37 cells.
Qin, Junhu,Zhu, Mei,Zhu, Hongmei,Zhang, Liqiong,Fu, Yihong,Liu, Jiamin,Wang, Zhenchao,OuYang, Guiping
p. 592 - 599
(2020/03/16)

Synthesis methods for isothiocyanate derivative
The invention discloses synthesis methods for an isothiocyanate derivative. The first synthesis method includes reacting raw materials, including primary amine, trifluoromethyltrimethylsilane, potassium fluoride and sulfur, with an organic solvent at the room temperature to obtain the isothiocyanate derivative. The synthetic isothiocyanate derivative has the advantages of simple operation, safety,high efficiency, non-toxicity, low raw material price, mild condition, high yield, wide application range of substrates, high compatibility of functional groups and the like. The second synthesis method includes reacting raw materials, including the primary amine, silver trifluoromethane and potassium bromide, with the organic solvent at the room temperature to obtain the isothiocyanate derivative. The isothiocyanate derivative has the advantages of simple operation, safety, high efficiency, easy availability of the raw materials, nearly quantitative yield, wide application range of the substrates, applicability to selective post-modification of drugs or complex compounds, and the like.
-
Paragraph 0033; 0034; 0035; 0036; 0077; 0078; 0079; 0080

(2019/05/22)

Synthesis of thiocarbamoyl fluorides and isothiocyanates using CF3SiMe3 and elemental sulfur or AgSCF3 and KBr with amines
Reactions of thiocarbonyl fluoride derived from cheap, readily available, and widely used CF3SiMe3, elemental sulfur, and KF with secondary amines and primary amines at room temperature in THF provided a wide variety of thiocarbamoyl fluorides and isothiocyanates in moderate to excellent yields, respectively. The two reactions show broad substrate scope and good functional group tolerance. Moreover, AgSCF3 reacts with secondary/primary amines under KBr at room temperature, affording quantitative thiocarbamoyl fluorides/isothiocyanates, which feature late-stage application.
Zhen, Long,Fan, Hui,Wang, Xiaoji,Jiang, Liqin
supporting information
p. 2106 - 2110
(2019/03/26)

Isothiocyanate-Directed Ortho-Selective Halogenation of Arenes via C–H Functionalization
Abstract: Ortho-selective halogenation of arenes via C–H functionalization has been described under mild reaction conditions. In this reaction Cu(II)X2 was used as a halide source. It is a simple, general and efficient method for the synthesis of 2-halo aromatic isothiocyanates. All the reactions are carried out under optimized reaction conditions to provide their respective desired products in good to high yield. Graphical Abstract: We have developed a general, simple and efficient method for the synthesis of 2-halo arylisothiocyanates from isothiocyanates through ortho-selective halogenation under mild reaction conditions. Cu(II)X2 was used as a halide source for this methodology. All the reactions are carried out under optimized reaction conditions to provide their respective desired products in good to high yield. [Figure not available: see fulltext.].
Mandapati, Usharani,Pinapati, Srinivasarao,Tamminana, Ramana,Rameshraju, Rudraraju
p. 418 - 423
(2017/11/29)

N-Aryl-N’-ethyleneaminothioureas effectively inhibit acetylcholinesterase 1 from disease-transmitting mosquitoes
Vector control of disease-transmitting mosquitoes by insecticides has a central role in reducing the number of parasitic- and viral infection cases. The currently used insecticides are efficient, but safety concerns and the development of insecticide-resistant mosquito strains warrant the search for alternative compound classes for vector control. Here, we have designed and synthesized thiourea-based compounds as non-covalent inhibitors of acetylcholinesterase 1 (AChE1) from the mosquitoes Anopheles gambiae (An. gambiae) and Aedes aegypti (Ae. aegypti), as well as a naturally occurring resistant-conferring mutant. The N-aryl-N’-ethyleneaminothioureas proved to be inhibitors of AChE1; the most efficient one showed submicromolar potency. Importantly, the inhibitors exhibited selectivity over the human AChE (hAChE), which is desirable for new insecticides. The structure-activity relationship (SAR) analysis of the thioureas revealed that small changes in the chemical structure had a large effect on inhibition capacity. The thioureas showed to have different SAR when inhibiting AChE1 and hAChE, respectively, enabling an investigation of structure-selectivity relationships. Furthermore, insecticidal activity was demonstrated using adult and larvae An. gambiae and Ae. aegypti mosquitoes.
Knutsson, Sofie,Kindahl, Tomas,Engdahl, Cecilia,Nikjoo, Dariush,Forsgren, Nina,Kitur, Stanley,Ekstr?m, Fredrik,Kamau, Luna,Linusson, Anna
p. 415 - 427
(2017/04/24)

N,N'-bis-substituted aryl thiourea derivatives and synthetic method and application thereof
The invention discloses N,N'-bis-substituted aryl thiourea derivatives which are a series of compounds simultaneously containing various substituted aromatic ring structures and asymmetric substituted thiourea structures and are all novel structural compounds which are not reported in the literature. The biological activity test analysis of all the target compounds includes determination of DPPH antioxidant activity and antiviral activity. Results indicate that, in general, the designed and synthesized compounds are novel in structures and have the antioxidant activity and the antiviral activity revealed for the first time. In addition, the unknown biological activity is not fully elucidated, and thus the compounds are expected to provide a certain material basis for further research and development of new drugs.
-
Paragraph 0080; 0087; 0088

(2017/04/26)

Isothiocyanation of amines using the Langlois reagent
The Langlois reagent was found to be effective for the isothiocyanation of primary amines in the presence of copper iodide and diethyl phosphonate.
Liao, Yan-Yan,Deng, Jian-Chao,Ke, Yan-Ping,Zhong, Xiao-Lin,Xu, Li,Tang, Ri-Yuan,Zheng, Wenxu
supporting information
p. 6073 - 6076
(2017/07/10)

Synthesis, structure-activity relationship and binding mode analysis of 4-thiazolidinone derivatives as novel inhibitors of human dihydroorotate dehydrogenase
A series of 4-thiazolidinone derivatives were synthesized and evaluated as novel human dihydroorotate dehydrogenase (hDHODH) inhibitors. Compounds 26 and 31 displayed IC50 values of 1.75 and 1.12 μM, respectively. The structure-activity relationship was summarized. Further binding mode analysis revealed that compound 31 could form a hydrogen bond with Tyr38 and a water-mediated hydrogen bond with Ala55, which may be necessary for maintaining the bioactivities of the compounds in this series. Further structural optimization of the para- or meta-position of the phenyl group at R will lead to the identification of more potent hDHODH inhibitors.
Zeng, Fanxun,Qi, Tiantian,Li, Chunyan,Li, Tingfang,Li, Honglin,Li, Shiliang,Zhu, Lili,Xu, Xiaoyong
supporting information
p. 1297 - 1302
(2017/07/07)

A novel one-pot synthesis of isothiocyanates and cyanamides from dithiocarbamate salts using environmentally benign reagent tetrapropylammonium tribromide
A highly efficient and simple protocol for the synthesis of isothiocyanates and cyanamides from their respective amines in the presence of a mild, efficient, and non-toxic reagent tetrapropylammonium tribromide is described. High environmental acceptability of the reagents, cost effectiveness and high yields are the important attributes of this methodology.
Kuotsu, Neivotsonuo Bernadette,Jamir, Latonglila,Phucho, Tovishe,Sinha, Upasana Bora
p. 832 - 841
(2018/01/17)

Double three bromo 1,3-di-pyridine salt-based propane and its preparation method, method of use, recovery method and application
The invention discloses a double tribromo 1,3-bipyridine onium salt dimethylmethane, and a preparation method, an application method, a recovery method and application thereof. The preparation method comprises the following steps: dissolving 1,3-bipyridine onium salt dimethylmethane by using water, and then adding potassium bromide; adding potassium peroxymonosulfate sulfate compound brine solution to prepare a clear solution after dissolving potassium bromide, and then stirring and reacting at -10 to 0 DEG C until solid is separated out; separating out solid, so as to obtain the double tribromo 1,3-bipyridine onium salt dimethylmethane. The product can be used for preparing isothiocyanate, aromatic thiourea or acetanilide. The preparation method disclosed by the invention is mild in condition, and simple to operate the reaction process, and raw materials are easily available. The double tribromo 1,3-bipyridine onium salt dimethylmethane not only can be used as a brominating reagent, but also can be used as organic synthesis intermediates, meanwhile, the reaction efficiency is improved, and the double tribromo 1,3-bipyridine onium salt dimethylmethane is convenient to recover and can be recycled.
-
Paragraph 0075; 0076; 0095; 0096

(2016/10/07)

Synthesis of 4-phenylthieno[2, 3-e][1, 2, 4]triazolo[4, 3-a]pyrimidine-5 (4H)-one derivatives and evaluation of their anti-inflammatory activity
A series of 4-phenylthieno[2, 3-e][1, 2, 4]triazolo[4, 3-a]pyrimidine-5 (4H)-ones (5a-p) with triazole or other heterocyclic substituents (6-11) was synthesized and the compounds were evaluated for their anti-inflammatory activity using the xylene-induced ear-edema test. Pharmacological analyses showed that the compound 4- (4-chlorophenyl)thieno[2, 3-e][1, 2, 4]triazolo[4, 3-a]pyrimidine- 5 (4H)-one (5m) exhibited the greatest anti-inflammatory activity (50.48% inhibition, 30 min after intraperitoneal administration) and was more potent than the reference drug, indomethacin. The peak activity of 5m was observed 4 h after oral administration, and it showed a higher anti-inflammatory activity than indomethacin did at a dose of 100 mg/kg.
Pan, Fu-Jun,Wang, Shi-Ben,Liu, Da-Chuan,Gong, Guo-Hua,Quan, Zhe-Shan
p. 141 - 148
(2016/03/12)

Facile and versatile synthesis of alkyl and aryl isothiocyanates by using triphosgene and cosolvent
A mild and efficient method for the conversion of alkyl and aryl amines to isothiocyanates via dithiocarbamates has been developed using (CH 3)2CO-CS2 as co-solvent and triphosgene as dehydrosulfurization reagent. High yields, mild reaction conditions and excellent functional group compatibility make it become a versatile synthetic method for the preparation of isothiocyanates compared with reported methods. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
Liu, Pengfei,Li, Chunyan,Zhang, Jingwei,Xu, Xiaoyong
supporting information
p. 3342 - 3351
(2013/10/01)

Synthesis of isothiocyanates by reaction of amines with phenyl chlorothionoformate via one-pot or two-step process
A facile and efficient synthesis of isothiocyanates from amines is described. This method involves the reaction of amines with phenyl chlorothionoformate in the presence of solid sodium hydroxide by either a one-pot process or a two-step approach. The one-pot process is useful for preparing alkyl and electron-rich aryl isothiocyanates, whereas the two-step approach is more versatile, working very well not only for alkyl and electron-rich aryl isothiocyanates, but also for highly electron-deficient aryl and heterocyclic isothiocyanates. Georg Thieme Verlag Stuttgart, New York.
Li, Zheng-Yi,Ma, Hong-Zhao,Han, Chen,Xi, Hai-Tao,Meng, Qi,Chen, Xin,Sun, Xiao-Qiang
p. 1667 - 1674
(2013/07/19)

A simple and straightforward synthesis of phenyl isothiocyanates, symmetrical and unsymmetrical thioureas under ball milling
Promoted by KOH under ball milling, anilines were efficiently transformed into isothiocyanates (in presence of 5.0 equiv. CS2) or symmetrical thioureas (in presence of 1.0 equiv. CS2), without using any other harsh or toxic decomposition reagent. Some in situ generated isothiocyanates can directly "click" with other amines to afford unsymmetrical thioureas.
Zhang, Ze,Wu, Hao-Hao,Tan, Ya-Jun
p. 16940 - 16944
(2013/09/24)

Tricyclic Compounds As mPGES-1 Inhibitors
The present invention relates to tricyclic compounds of formula (I) or pharmaceutically acceptable salt thereof as mPGES-1 inhibitors. These compounds are inhibitors of the microsomal prostaglandin E synthase-1 (mPGES-1) enzyme and are therefore useful in the treatment of pain and/or inflammation from a variety of diseases or conditions, such as asthma, osteoarthritis, rheumatoid arthritis, acute or chronic pain and neurodegenerative diseases.
-
Page/Page column 25

(2012/05/07)

Environmentally benign one-pot synthesis of cyanamides from dithiocarbamates using I2 and H2O2
An environmentally benign reaction is devised for the synthesis of cyanamides from dithiocarbamate salts using iodine and H2O 2. Taylor & Francis Group, LLC.
Jamir, Latonglila,Sinha, Upasana Bora,Nath, Jayashree,Patel, Bhisma K.
experimental part
p. 951 - 958
(2012/02/01)

A general and facile one-pot process of isothiocyanates from amines under aqueous conditions
A general and facile one-pot protocol for the preparation of a broad range of alkyl and aryl isothiocyanates has been developed from their corresponding primary amines under aqueous conditions. This synthetic process involves an in situ generation of a dithiocarbamate salt from the amine substrate by reacting with CS2 followed by elimination to form the isothiocyanate product with cyanuric acid as the desulfurylation reagent. The choice of solvent is of decisive importance for the successful formation of the dithiocarbamate salt particularly for highly electron-deficient substrates. This novel and economical method is suitable for scale-up activities.
Sun, Nan,Li, Bin,Shao, Jianping,Mo, Weimin,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
experimental part
p. 61 - 70
(2012/04/04)

Isatin-β-thiosemicarbazones as potent herpes simplex virus inhibitors
A series of isatin-β-thiosemicarbazones have been designed and evaluated for antiviral activity against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) in a plaque reduction assay. Their cytotoxicity was examined using human rhabdomyosarcoma cells (RD cells). Several derivatives of isatin-β-thiosemicarbazone exhibited significant and selective antiviral activity with low cytotoxicity. It was found that the thiourea group at thiosemicarbazone and the NH functionality at isatin were essential for their antiherpetic activity. The synthesis and structure-activity relationship studies are presented.
Kang, Iou-Jiun,Wang, Li-Wen,Hsu, Tsu-An,Yueh, Andrew,Lee, Chung-Chi,Lee, Yen-Chun,Lee, Ching-Yin,Chao, Yu-Sheng,Shih, Shin-Ru,Chern, Jyh-Haur
scheme or table
p. 1948 - 1952
(2011/05/04)

Diversity-orientated synthesis of 3,5-bis(arylamino)pyrazoles
The synthesis of differentially-substituted 3,5-bis(arylamino)pyrazoles has not yet been documented. During our investigation, we managed to develop a novel, entirely combinatorial synthesis of 3,5-bis(arylamino)pyrazoles relying on a simple one-pot two-step operation.
Degorce, Sébastien,Jung, Frédéric H.,Harris, Craig S.,Koza, Patrice,Lecoq, Jonathan,Stevenin, Arnaud
supporting information; experimental part
p. 6719 - 6722
(2012/01/05)

Synthesis and reactivity studies of a new reagent, ethyltriphenylphosphonium tribromide
A new reagent, ethyltriphenyl phosphonium tribromide (ETPPTB), has been synthesized and studied. Results show that the reagent is quite efficient for various reactions such as organic bominations, acylations, and isothiocyanate preparation. Copyright
Jamir, Latonglila,Alimenla,Kumar, Anil,Sinha, Dipak,Sinha, Upasana B.
experimental part
p. 147 - 155
(2011/03/17)

Structure-activity relationships (SAR) research of thiourea derivatives as dual inhibitors targeting both HIV-1 capsid and human cyclophilin A
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
scheme or table
p. 25 - 33
(2011/04/17)

Efficient preparation of isothiocyanates from dithiocarbamates using bromineless brominating reagent
For the first time, the crystal structure of a ditribromide reagent 1,1'-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) has been determined. Utilizing this thiophilic bromineless brominating agent EDPBT, highly useful synthetic intermediates (alkyl and aryl isothiocyanates) have been achieved directly from dithiocarbamates. EDPBT can be easily prepared from readily available reagents. It has been used as a thiophilic reagent, and its thiophilicity dominates over its brominating ability for substrates amenable to bromination. This is a sustainable process for the preparation of isothiocyantes because the spent reagent can be recovered, regenerated, and reused. Copyright Taylor & Francis Group, LLC.
Yella, Ramesh,Ghosh, Harisadhan,Murru, Siva,Sahoo, Santosh K.,Patel, Bhisma K.
experimental part
p. 2083 - 2096
(2010/08/19)

Molecular iodine mediated preparation of isothiocyanates from dithiocarbamic acid salts
We have developed a general economical and environmentally benign method for the preparation of isothiocyanates from the corresponding dilhiocarbamic acid salts by using cheap and readily available reagent molecular iodine. This is perhaps the most efficient method reported so far for the synthesis of isothiocyanates. The reagent is easily available and nontoxic, and the precipitated sulfur can be removed easily; hence, this method is most suitable for large-scale synthesis. Wiley-VCH Verlag GmbH & Co. KGaA.
Nath, Jayashree,Ghosh, Harisadhan,Yella, Mamesh,Patel, Bhisma K.
experimental part
p. 1849 - 1851
(2009/08/07)

A one-pot preparation of cyanamide from dithiocarbamate using molecular iodine
An efficient one-pot method for the synthesis of cyanamides from dithiocarbamate salts via a double desulfurization strategy using molecular iodine is disclosed. Dithiocarbamates, by the action of iodine yield isothiocyanates in situ, which on treatment with aqueous NH3 give thioureas. The thioureas so generated undergo further oxidative desulfurization with I2 giving corresponding cyanamides in good yields. Environmental benignity, cost effectiveness and high yields are the important attributes of this one pot procedure. The Royal Society of Chemistry 2009.
Nath, Jayashree,Patel, Bhisma K.,Jamir, Latonglila,Sinha, Upasana Bora,Satyanarayana
experimental part
p. 1503 - 1506
(2010/05/18)

Novel synthesis of anthelmintic drug 4-isothiocyanato-4′- nitrodiphenyl ether and its analogs
An efficient, mild, chemoselective, and convenient protocol for synthesis of isothiocyanate derivatives. This protocol was applied successfully in the novel synthesis of anthelmintic drug 4-isothiocyanato-4′-nitrodiphenyl ether and its analogs. Copyright Taylor & Francis Group, LLC.
Chaskar,Bandgar,Modhave,Patil,Yewale
body text
p. 992 - 1001
(2009/09/08)

Desulfurization mediated by hypervalent iodine(III): A novel strategy for the construction of heterocycles
The desulfurization ability of diacetoxyiodobenzene (DIB) has been explored in the preparation of isothiocyanates from the corresponding dithiocarbamate salts. The in situ generated isothiocyanates reacted with o-phenylenediamine and o-aminophenol to form monothioureas, which, on treatment with a further equivalent of DIB in one pot, gave benzimidazoles and aminobenzoxazoles, respectively. Aliphatic 1,2-diamines on reaction with 2 equiv. of isothiocyanate followed by treatment with DIB gave imidazolidenecarbothioamides, whereas the treatment of aromatic 1,2-diaminebis(thioureas) yielded benzimidazoles with the concurrent formation of isothiocyanate. The driving force for the formation of the latter is the aromatization of the product. The use of DIB makes these methods simpler and more efficient, giving high yields of the desired products in one pot. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Ghosh, Harisadhan,Yella, Ramesh,Nath, Jayashree,Patel, Bhisma K.
scheme or table
p. 6189 - 6196
(2009/05/27)

2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 1: Discovery of CB2 receptor selective compounds
2-Arylimino-5,6-dihydro-4H-1,3-thiazines have been identified as a novel class of cannabinoid agonists. A lead structure with moderate activity was discovered through a high throughput screening assay. Structure-activity relationships led to the discovery of potent agonists of CB2 receptor. The most potent compound 13 displays Ki values of >5000 and 9 nM to CB1 and CB2 receptors, respectively.
Kai, Hiroyuki,Morioka, Yasuhide,Murashi, Takami,Morita, Koichi,Shinonome, Satomi,Nakazato, Hitoshi,Kawamoto, Keiko,Hanasaki, Kohji,Takahashi, Fumiyo,Mihara, Shin-ichi,Arai, Tohko,Abe, Kohji,Okabe, Hiroshi,Baba, Takahiko,Yoshikawa, Takayoshi,Takenaka, Hideyuki
p. 4030 - 4034
(2008/02/08)

Isothiocyanates from tosyl chloride mediated decomposition of in situ generated dithiocarbamic acid salts
(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.
p. 3969 - 3971
(2008/02/01)

Syntheses, structures and bioactivities of fluorine-containing phenylimino-thia(oxa)zolidine derivatives as agricultural bioregulators
From insight into the structure of trehazolin as trehalase inhibitor, six series of fluorine-containing phenylimino-thiazolidines (oxazolidines) derivatives were designed and prepared through a convenient synthesis of fluoroaryl isothiocyanate and a one-pot facile synthesis in high yield of fluorophenyl aminobenzoxazoles by cyclodesulfurization. The structures of the target compounds were confirmed with using IR, NMR, MS and elemental analysis. Their X-ray crystal analysis suggested that there were novel intermolecular (sp2CF?H3C) and intramolecular (sp 2CF?HN) hydrogen bonds between the fluorine atom on benzene ring and hydrogen atom of methyl group or amino group on five-membered heterocycle. Their fungicidal activities against Rhizoctonia solani and Pyricuraria oryzae at 100 ppm were determined. From insight into the structure of trehazolin as trehalase inhibitor, six series of fluorine-containing phenylimino-thiazolidines (oxazolidines) derivatives were designed and prepared through a convenient synthesis of fluoroaryl isothiocyanate and a one-pot facile synthesis in high yield of fluorophenyl aminobenzoxazoles by cyclodesulfurization. The structures of the target compounds were confirmed with using IR, NMR, MS and elemental analysis. Their X-ray crystal analysis suggested that there were novel intermolecular (sp2CF?H 3C) and intramolecular (sp2CF?HN) hydrogen bonds between the fluorine atom on benzene ring and hydrogen atom of methyl group or amino group on five-membered heterocycle. Their fungicidal activities against Rhizoctonia solani and Pyricuraria oryzae at 100 ppm were determined. fx1
Qian, Xuhong,Xu, Xiaoyong,Li, Zhibin,Li, Zhong,Song, Gonghua
p. 1609 - 1620
(2007/10/03)

Synthesis of thiophene-2-carboxamidines containing 2-aminothiazoles and their biological evaluation as urokinase inhibitors
The serine protease urokinase (uPa) has been implicated in the progression of both breast and prostate cancer. Utilizing structure based design, the synthesis of a series of substituted 4-[2-amino-1,3-thiazolyl]-thiophene-2-carboxamidines is described. Further optimization of this series by substitution of the terminal amine yielded urokinase inhibitors with excellent activities.
Wilson, Kenneth J.,Illig, Carl R.,Subasinghe, Nalin,Hoffman, James B.,Jonathan Rudolph,Soll, Richard,Molloy, Christopher J.,Bone, Roger,Green, David,Randall, Troy,Zhang, Marie,Lewandowski, Frank A.,Zhou, Zhao,Sharp, Celia,Maguire, Diane,Grasberger, Bruce,DesJarlais, Renee L.,Spurlino, John
p. 915 - 918
(2007/10/03)

A facile synthesis of aryl isothiocyanates from arylamines
-
Li, Zhibin,Qian, Xuhong,Liu, Zhi,Li, Zhong,Song, Gonghua
p. 571 - 573
(2007/10/03)

A facile one-pot preparation of isothiocyanates from aldoximes
Isothiocyanates 2a-l were prepared in excellent yields in a one-pot reaction from aldoxime derivatives 1a-l by successive treatment of aldoxime with N-chlorosuccinimide (NCS), thiourea, and triethylamine. The use of HCl/DMF/Oxone system in the reaction instead of NCS was equally effective.
Kim, Jae Nyoung,Jung, Keum Shin,Lee, Hong Jung,Son, Ji Suk
p. 1597 - 1598
(2007/10/03)

A convenient synthesis of isothiocyanates from primary nitroalkanes
The reaction of primary nitroalkanes with thiourea in the presence of 4-chlorophenyl isocyanate and a catalytic amount of triethylamine in benzene afforded isothiocyanates in moderate yields.
Kim,Song,Ryu
p. 1101 - 1105
(2007/10/02)

A convenient synthesis of isothiocyanates from nitrile oxides
Isothiocyanats were prepared in quantitative yields from the reaction of nitrile oxides with thiourea in tetrahydrofuran at room temperature in short time.
Kim, Jae Nyoung,Ryu, Eung K.
p. 8283 - 8284
(2007/10/02)

Synthesis and Reaction of 2-Imino-1,3-thiazetidines and 2-Imino-1,3-dithietanes
2-Imino-1,3-thiazetidines and 2-imino-1,3-dithietanes were synthesized and their reactivities were studied.The former readily underwent ring-opening reaction with amines to yield guanidine derivatives.The reaction products were applied to the synthesis of heterocycles such as triazoles and triazines.The latter was converted to isothiocyanate by the reaction of m-chloroperbenzoic acid.
Okajima, Nobuyuki,Okada, Yoshiyuki
p. 177 - 185
(2007/10/02)

Novel reactions of S,S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate
S,S'-Bis(1-phenyl-1H-5-yl) dithiocarbonate (1) was synthesized in good yield from 1-phenyl-5-mercapto-5H-tetrazole (2) and trichloromethyl chloroformate (TCF).The structure of 1 was confirmed by using X-ray crystal analysis.The reagent (1) could be applied to the formation of amides, Friedel-Crafts type reactions, isothiocyanate syntheses, and carbonyl group insertion reactions.Keywords - S,S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate; X-ray crystal analysis; amide; isothiocyanate; Friedel-Crafts reaction; carbonyl group insertion reaction.
Takeda, Kazuyoshi,Tsuboyama, Kanoko,Takayanagi, Hiroaki,Shirokami, Rie,Takeura, Masumi,Ogura, Haruo
p. 2334 - 2337
(2007/10/02)

ORGANOARSENIC COMPOUNDS WITH AN As=N BOND. III. REACTIONS OF TRICHLORODIPHENYLARSORANE WITH PRIMARY AROMATIC AMINES. As,AS,N,N'-TETRAARYLARSINIMIDIC AMIDES AND THEIR PROPERTIES
-
Kokorev, G. I.,Yambushev, F. D.,Al'metkina, L. A.
p. 2302 - 2304
(2007/10/02)

Degradation in Aqueous Solution of O-Aryl N-Arylthioncarbamates to Aryloxide Ions and Isothiocyanates. A Study of Leffler's Assumption
Rate constants for the title reaction have been measured in both forward and reverse directions leading to rates and equilibrium constants for all steps in equation (i).The effects of varying the structures of Ar and Ar' on the equilibrium and rate constants were measured; identical Leffler-Grunwald indices (α=βF/βEQ=d log k/d log K) for the addition step are observed for variation in Ar and Ar' although individual β values are markedly different.Identical α parameters arising from different substituent interaction pathways to a single bond are required if the reaction conforms to the Leffler assumption; on this basis the α parameter is considered a good measure of transition-state structure relative to reactant- and product-states for the addition reaction. 'Effective charges' on the phenolic oxygen in the thioncarbamate and its conjugate base indicate considerable C(1+)-S(1-) character in the formal thioncarbamoyl bond.
Hill, Stephen V.,Thea, Sergio,Williams, Andrew
p. 437 - 446
(2007/10/02)

Heterocycles from Nitrile Oxides. I. 5-Imino-Δ2-1,4,2-Oxathiazolines
The reaction of some arylnitrile oxides with potassium thiocyanate in acetone at ambient temperature, has been investigated.Those having para- or meta-halo (or nitro) substituents give 3-aryl-5-imino-Δ2-1,4,2-oxathiazolines as stable cycloadducts. ortho-Substitution, on the other hand, led directly to the corresponding 5-(carbamido)imino analogues.The structures of these new heterocycles are supported by elemental analyses and spectral data.
Hussein, Ahmed Q.,El-Abadelah, Mustafa M.,Sabri, Wail S.
p. 301 - 304
(2007/10/02)