- A facile preparation of selenohydantoins using isoselenocyanate
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(Chemical Equation Presented) Reactions of isoselenocyanate with methyl aminoacetate hydrochlorides in the presence of triethylamine afforded selenohydantoins, 2-selenoxoimidazolidin-4-ones, in high yields.
- Koketsu, Mamoru,Takahashi, Ayako,Ishihara, Hideharu
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Read Online
- Room-Temperature Metal-Free Multicomponent Polymerizations of Elemental Selenium toward Stable Alicyclic Poly(oxaselenolane)s with High Refractive Index
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Selenium-containing polymers are a group of fascinating functional polymers with unique structures, properties, and applications, which have been developed recently but only with limited examples. The challenges of developing selenium-containing polymers
- Wu, Xiuying,He, Junxia,Hu, Rongrong,Tang, Ben Zhong
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supporting information
p. 15723 - 15731
(2021/10/01)
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- Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XI. 1-[(Adamantan-1 yl)alkyl]-3-arylselenoureas
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Abstract: A series of N,N′-disubstituted selenoureas containing an adamantane fragmenthave been synthesized in 23–75% yields. Procedures for the isolation andpurification of aromatic isoselenocyanates have been improved. The chemicalshift of the C=Se carbon nucleus in the 13C NMRspectra of selenoureas has been refined. The synthesized selenoureas have beenfound to be promising as inhibitors of not only epoxide hydrolase (sEH-H) butalso phosphatase domains (sEH-P) of human soluble epoxide hydrolase.
- Kuznetsov, Ya. P.,Rasskazova,Pitushkin,Eshtukov,Vasipov,Burmistrov,Butov
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p. 1036 - 1046
(2021/09/08)
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- The Importance of 1,5-Oxygen???Chalcogen Interactions in Enantioselective Isochalcogenourea Catalysis
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The importance of 1,5-O???chalcogen (Ch) interactions in isochalcogenourea catalysis (Ch=O, S, Se) is investigated. Conformational analyses of N-acyl isochalcogenouronium species and comparison with kinetic data demonstrate the significance of 1,5-O???Ch interactions in enantioselective catalysis. Importantly, the selenium analogue demonstrates enhanced rate and selectivity profiles across a range of reaction processes including nitronate conjugate addition and formal [4+2] cycloadditions. A gram-scale synthesis of the most active selenium analogue was developed using a previously unreported seleno-Hugerschoff reaction, allowing the challenging kinetic resolutions of tertiary alcohols to be performed at 500 ppm catalyst loading. Density functional theory (DFT) and natural bond orbital (NBO) calculations support the role of orbital delocalization (occurring by intramolecular chalcogen bonding) in determining the conformation, equilibrium population, and reactivity of N-acylated intermediates.
- Cockroft, Scott L.,Elmi, Alex,Frost, Aileen B.,Ling, Kenneth B.,McLaughlin, Calum,Morris, Rylie K.,Pascoe, Dominic J.,Slawin, Alexandra M. Z.,Smith, Andrew D.,Smith, Terry K.,Willoughby, Patrick H.,Woods, Andrew M.,Young, Claire M.,de la Houpliere, Alix
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supporting information
p. 3705 - 3710
(2020/02/11)
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- Bis-Selenoureas for Anion Binding: A 1H NMR and Theoretical Study
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The anion binding ability of a family of bis-selenoureas L1-L3 obtained by the reaction of 1,3-bis(aminomethyl)-benzene and phenylisoselenocyanate, p-methoxyphenylisoselenocyanate and naphtylisoselenocyanate, for L1, L2, and L3, respectively, has been tested and compared to that of previously described bis-urea analogues. Results suggest that the introduction of selenium leads to an increase in the acidity of the urea NH hydrogen atoms, and therefore to a stronger affinity (more than three-fold higher) towards anion species, in particular dihydrogen phosphate, in DMSO-d6. Theoretical calculations allowed for the optimization of the adducts receptors corroborating the experimental results.
- Caltagirone, Claudia,Ciancaleoni, Gianluca,Lippolis, Vito,Mocci, Rita,Picci, Giacomo,Zielińska-B?ajet, Mariola
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p. 1389 - 1395
(2020/08/05)
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- Synthesis and leishmanicidal activity of novel urea, thiourea, and selenourea derivatives of diselenides
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A novel series of thirty-one N-substituted urea, thiourea, and selenourea derivatives containing diphenyldiselenide entities were synthesized, fully characterized by spectroscopic and analytical methods, and screened for their in vitro leishmanicidal activities. The cytotoxic activity of these derivatives was tested against Leishmania infantum axenic amastigotes, and selectivity was assessed in human THP-1 cells. Thirteen of the synthesized compounds showed a significant antileishmanial activity, with 50% effective concentration (EC50) values lower than that for the reference drug miltefosine (EC50, 2.84 M). In addition, the derivatives 9, 11, 42, and 47, with EC50 between 1.1 and 1.95 M, also displayed excellent selectivity (selectivity index ranged from 12.4 to 22.7) and were tested against infected macrophages. Compound 11, a derivative with a cyclohexyl chain, exhibited the highest activity against intracellular amastigotes, with EC50 values similar to those observed for the standard drug edelfosine. Structure-activity relationship analyses revealed that N-aliphatic substitution in urea and selenourea is recommended for the leishmanicidal activity of these analogs. Preliminary studies of the mechanism of action for the hit compounds was carried out by measuring their ability to inhibit trypanothione reductase. Even though the obtained results suggest that this enzyme is not the target for most of these derivatives, their activity comparable to that of the standards and lack of toxicity in THP-1 cells highlight the potential of these compounds to be optimized for leishmaniasis treatment.
- Díaz, Marta,de Lucio, Héctor,Moreno, Esther,Espuelas, Socorro,Aydillo, Carlos,Jiménez-Ruiz, Antonio,Toro, Miguel ángel,Gutiérrez, Killian Jesús,Martínez-Merino, Victor,Cornejo, Alfonso,Palop, Juan Antonio,Sanmartín, Carmen,Planoa, Daniel
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- Novel 1,3,4-Selenadiazole-Containing Kidney-Type Glutaminase Inhibitors Showed Improved Cellular Uptake and Antitumor Activity
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Kidney-type glutaminase [KGA/isoenzyme glutaminase C (GAC)] is becoming an important tumor metabolism target in cancer chemotherapy. Its allosteric inhibitor, CB839, showed early promise in cancer therapeutics but limited efficacy in in vivo cancer models. To improve the in vivo activity, we explored a bioisostere replacement of the sulfur atom in bis-2-(5-phenylacetamido-1,2,4-thiadiazol)ethyl sulfide and CB839 analogues with selenium using a novel synthesis of the selenadiazole moiety from carboxylic acids or nitriles. The resulting selenadiazole compounds showed enhanced KGA inhibition, more potent induction of reactive oxygen species, improved inhibition of cancer cells, and higher cellular and tumor accumulation than the corresponding sulfur-containing molecules. However, both CB839 and its selenium analogues show incomplete inhibition of the tested cancer cells, and a partial reduction in tumor size was observed in both the glutamine-dependent HCT116 and aggressive H22 liver cancer xenograft models. Despite this, tumor tissue damage and prolonged survival were observed in animals treated with the selenium analogue of CB839.
- Chen, Zhao,Li, Di,Xu, Ning,Fang, Jinzhang,Yu, Yan,Hou, Wei,Ruan, Haoqiang,Zhu, Panpan,Ma, Renchao,Lu, Shiying,Cao, Danhui,Wu, Rui,Ni, Mowei,Zhang, Wei,Su, Weike,Ruan, Benfang Helen
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supporting information
p. 589 - 603
(2019/01/10)
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- A novel and convenient synthesis of 3-amino-2H-1,2,4-triazoles from isoselenocyanates and hydrazine hydrate
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A novel and convenient one-pot synthesis of 3-amino-2H-1,2,4-triazoles from two molecules of isoselenocyanates and hydrazine hydrate via cyclodeselenisation was developed. Various 3-amino-2H-1,2,4-triazoles were obtained in moderate to good yields (33-45%
- Li, Xue,Peng, Zhixiang,Zhang, Yuanyuan,Wang, Jiangwei,Gan, Bin,Xie, Yuanyuan
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p. 255 - 259
(2018/06/29)
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- Discovery of New Selenoureido Analogues of 4-(4-Fluorophenylureido)benzenesulfonamide as Carbonic Anhydrase Inhibitors
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A series of benzenesulfonamides bearing selenourea moieties was obtained considering the ureido-sulfonamide SLC-0111, in Phase I clinical trials as antitumor agent, as a lead molecule. All compounds showed interesting inhibition potencies against the physiologically relevant human (h) carbonic anhydrase (hCAs, EC 4.2.1.1) isoforms I, II, IV, and IX. The most flexible analogues in the series 14-19 showed low nanomolar inhibition constants against hCA I, II, and IX. We assessed selected compounds on the in vitro antioxidant properties and binding modes and evaluated ex vivo human prostate (PC3), breast (MDA-MB-231), and colon-rectal (HT-29) cancer cell lines both in normoxic and hypoxic conditions.
- Angeli, Andrea,Tanini, Damiano,Peat, Thomas S.,Di Cesare Mannelli, Lorenzo,Bartolucci, Gianluca,Capperucci, Antonella,Ghelardini, Carla,Supuran, Claudiu T.,Carta, Fabrizio
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p. 963 - 968
(2017/09/22)
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- Thermal stability and decomposition of urea, thiourea and selenourea analogous diselenide derivatives
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The fusion and thermal decomposition of thirty-three diselenide compounds with a urea, thiourea or selenourea group linked with different aliphatic or aromatic substituents have been studied by thermogravimetry, differential scanning calorimetry and mass spectrometry in order to perform comparative thermal stability studies among analogs. A relationship has been found between stability and a series of effects which occur in the compound structures. Analysis of the thermal data indicated that: (a) in general, compounds with a urea or selenourea group are more stable than those with a thiourea group; (b) no difference in stability exists when an aromatic or aliphatic group is linked to the thiourea group but when linked to the urea or selenourea groups, stability does differ; (c) selenourea compounds with aliphatic chain are the most unstable; and (d) the nature of the substituent located on the benzyl ring has no effects on thermal stability. Therefore, criteria for the selection of substituents can be established in order to improve the stability of these drugs. In addition, the mass spectral fragmentation in comparison with thermal analytical data helps in confirming the thermal behavior of the compounds.
- Díaz, Marta,Palop, Juan Antonio,Sanmartín, Carmen,Lizarraga, Elena
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p. 1663 - 1674
(2017/02/10)
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- Synthesis of selenium analogues of 1-azabicyclo[4.4.0]decane
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An approach to the synthesis of selenium bicyclic structures of the 1-azabicyclo[4.4.0]decane series was developed, which included the condensation of aryl isoselenocyanates with 2-(2-bromoethyl)piperidine and subsequent intramolecular cyclization of sele
- Serkov,Proshin
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p. 298 - 300
(2016/11/06)
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- Synthesis of Isoselenocyanates
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Isoselenocyanates were synthesized by two methods under phase-transfer conditions (50% aq NaOH, CH2Cl2, Aliquat 336); the first started from isocyanides and selenium and gave isoselenocyanates in 61-89% yields, while the second started from amines and used chloroform and selenium, by applying sequentially the Hofmann isonitrile synthesis and the addition of selenium, in 4-70% yields.
- Zakrzewski, Jerzy,Huras, Bogumi?a,Kie?czewska, Anna
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- Synthesis of selenazolopyridine derivatives with capability to induce apoptosis in human breast carcinoma MCF-7 cells through scavenge of intracellular ROS
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A series of selenazolopyridine derivatives have been synthesized and characterized by X-ray diffraction, high resolution NMR and Mass spectrum. The in vitro anticancer activities of the synthetic compounds were screened against a panel of human cancer cell lines, human breast carcinoma MCF-7 cells, human liver carcinoma HepG2 cells and L02 normal cell line by MTT assay. By analyzing the structure-activity relationship among the synthetic compounds, it was found that 2-(phenylamino) selenazolo [5,4-b] pyridine, (PSeD, 7) had higher growth inhibitory effect on MCF-7 cells. The intracellular mechanism of cell death was evaluated by flow cytometric analysis and ROS assay, which revealed that PSeD could induce MCF-7 cells apoptosis by scavenging intracellular ROS. Taken together, we regard PSeD as an antioxidant which could inhibit cancer cell growth through induction of apoptosis.
- Zhou, Meiyun,Ji, Shengbin,Wu, Zhaojun,Li, Yiqun,Zheng, Wenjie,Zhou, Hua,Chen, Tianfeng
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- Regioselective one-pot three component synthesis of chiral 2-iminoselenazolines under sonication
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A one-pot multi component reaction of selenoureas, which are in situ generated from l-amino esters and isoselenocyanates, with α-bromoketone under ultrasonication. Selenourea and α-bromoketones formed 2-iminoselenazoles through a Hantzsch selenazole-type reaction. The steric effect of the α-substituted bromoketones on the rate of the tandem reaction was studied to understand the reaction mechanism by isolating the key reaction intermediate, 2-iminoselenol.
- Chang, Wong-Jin,Kulkarni, Manohar V.,Sun, Chung-Ming
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p. 97113 - 97120
(2015/12/01)
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- 1-Substituted-5-[(3,5-dinitrobenzyl)sulfanyl]-1H-tetrazoles and their isosteric analogs: A new class of selective antitubercular agents active against drug-susceptible and multidrug-resistant mycobacteria
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In this work, a new class of highly potent antituberculosis agents, 1-substituted-5-[(3,5-dinitrobenzyl)sulfanyl]-1H-tetrazoles and their oxa and selanyl analogs, is described. The minimal inhibitory concentration (MIC) values reached 1 μM (0.36-0.44 μg/mL) against Mycobacterium tuberculosis CNCTC My 331/88 and 0.25-1 μM against six multidrug-resistant clinically isolated strains of M. tuberculosis. The antimycobacterial effects of these compounds were highly specific because they were ineffective against all eight bacterial strains and eight fungal strains studied. Furthermore, these compounds exhibited low in vitro toxicity in four mammalian cell lines (IC50 > 30 μM). We also examined the structure-activity relationships of the compounds, particularly the effects on antimycobacterial activity of the number and position of the nitro groups, the linker between tetrazole and benzyl moieties, and the tetrazole itself. Relatively high variability of substituent R 1 on the tetrazole in the absence of negative effects on antimycobacterial activity allows further structural optimization with respect to toxicity and the ADME properties of the 1-substituted-5-[(3,5-dinitrobenzyl) sulfanyl]-1H-tetrazoles lead compounds.
- Karabanovich, Galina,Roh, Jaroslav,Smutny, Tomá?,Něme?ek, Jan,Vicherek, Petr,Stola?íková, Ji?ina,Vejsová, Marcela,Dufková, Ida,Vávrová, Kate?ina,Pávek, Petr,Klime?ová, Věra,Hrabálek, Alexandr
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p. 324 - 340
(2014/06/24)
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- One-pot synthesis of 1-substituted-5-alkylselanyl-1H-tetrazoles from isoselenocyanates: Unexpected formation of N-alkyl-N-arylcyanamides and (Z)-Se-alkyl-N-cyano-N,N′-diarylisoselenoureas
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1-Substituted-5-alkylsulfanyl-1H-tetrazoles are well known class of organic substances with various applications in medicinal chemistry or photographic industry. Their selenium analogues, 1-substituted-5-alkylselanyl-1H-tetrazoles are, however, much less explored because of the lack of suitable methods for their preparation. In this work we investigated the synthesis of 1-alkyl/aryl-5-alkylselanyl-1H-tetrazoles from synthetically available alkyl/arylisoselenocyanates. One-pot reactions of arylisoselenocyanates with sodium azide and alkylating agent led to the target 5-alkylselanyl-1-aryl-1H- tetrazoles but also to interesting side products, namely N-alkyl-N- arylcyanamides and (Z)-Se-alkyl-N-cyano-N,N′-diarylisoselenoureas. Nevertheless, when alkylisoselenocyanates were utilized as the substrates, the reactions led exclusively to the formation of 1-alkyl-5-alkylselanyl-1H- tetrazoles in good yields. This simple one-pot procedure brings new possibilities for the preparation of variously substituted selenium compounds. It also opens the way to further investigations of selenium isosteres of the widely utilized 5-thiotetrazole moiety in biomedical applications.
- Karabanovich, Galina,Roh, Jaroslav,Padělková, Zdeňka,Novák, Zdeněk,Vávrová, Kate?ina,Hrabálek, Alexandr
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p. 8798 - 8808
(2013/09/23)
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- Novel bicyclic derivatives of 1,3-selenazine
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Bicyclic isoselenoureas (1-selena-3-azaspiro[5.5]undec-2-en-2-ylamines and 3-selena-1-azabicyclo[3.3.1]non-2-ylideneamines) were obtained by intramolecular cyclization of selenoureas leading to 1,3-selenazine ring formation and tested for antioxidant acti
- Proshin,Serkov,Lermontov,Shevtsova,Neganova,Bachurin
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p. 142 - 146
(2013/11/19)
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- "On water": Efficient iron-catalyzed cycloaddition of aziridines with heterocumulenes
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In suspension: The reaction of aziridines with heterocumulenes in the presence of Fe(NO3)3×9 H2O in aqueous suspension provides access to functionalized five-membered heterocycles in good to high yields. This protocol has a wide substrate scope, is simple, and uses a nontoxic and cheap catalyst. Copyright
- Sengoden, Mani,Punniyamurthy, Tharmalingam
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supporting information
p. 572 - 575
(2013/02/23)
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- Synthesis and pesticidal properties of thio and seleno analogs of some common urea herbicides
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Thio and seleno analogs of fenuron, isoproturon, chlorotoluron, metoxuron, monuron, and diuron were synthesized from the corresponding aryl amines. Their reaction with thiophosgene leads to isothiocyanates. Aryl amines were also converted (via isocyanides) to isoselenocyanates. The reaction of both isothio- and isoselenocyanates with dimethylamine affords the corresponding thio and seleno analogs of the above-mentioned urea herbicides. Herbicidal activity of the synthesized compounds was slightly lower than the activity of the parent urea herbicides. The thio and seleno analogs as well as the parent ureas showed good fungicidal activity at a concentration of 200 ppm against selected fungi.
- Zakrzewski, Jerzy,Krawczyk, Maria
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experimental part
p. 1880 - 1903
(2010/02/28)
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- Synthesis of sugar-derived isoselenocyanates, selenoureas, and selenazoles
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Aryl, alkyl, and sugar-derived isoselenocyanates were prepared by a one-pot procedure starting from the corresponding formamides, using triphosgene as a dehydrating agent, triethylamine, and black selenium powder. The preparation of sugar selenoureas by coupling of O-protected sugar-derived isoselenocyanates with different amines, and by coupling of unprotected glycopyranosyl amines with phenyl isoselenocyanate was also accomplished. The synthesis of a glucopyranos-2-yl-selenazole starting from O-protected 2-amino-2-deoxy-d-glucose by coupling with benzoyl isoselenocyanate, Se-alkylation with phenacyl bromide, and acid-catalyzed dehydration is also reported. Unprotected N-(β-d-glucopyranosyl)-N′-phenylselenourea was transformed into a 1,2-trans-fused bicyclic isourea upon treatment with aqueous hydrogen peroxide; the same isourea was prepared by a one-pot three-step procedure from β-d-glycopyranosylamine by thiophosgenation, coupling with aniline, and HgO-mediated desulfurization.
- López, óscar,Maza, Susana,Ulgar, Víctor,Maya, Inés,Fernández-Bola?os, José G.
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experimental part
p. 2556 - 2566
(2009/08/08)
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- Gold(I) phosphine complexes containing selenocarbamate esters: Crystal and molecular structure of N-phenyl-O-methylselenocarbamate
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A series of both mono- and dinuclear gold(I) phosphine complexes containing deprotonated N-phenyl-O-methylselenocarbamate of the type [AuSeC(OMe) = NPh(P)] and [Au2SeC(OMe) = NPh2(PP)] (P = PPh3, P(o-tolyl)3, PTA; PP = dppm, dppe, dppp, dppf) were prepared and characterized by spectroscopic techniques. The X-ray crystal structure of SeC(OMe)=N(H)Ph is also reported and shows the molecule to exist in the E-conformation. Centrosymmetrically related dimers associate in the crystal structure by N-H...Se interactions.
- Gallenkamp, Daniel,Tiekink, Edward R. T.,Mohr, Fabian
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scheme or table
p. 1050 - 1056
(2009/04/06)
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- Selenium-containing heterocycles from isoselenocyanates: 4-Methylselenazole derivatives from the reaction with malononitrile and propargyl chloride
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Aryl isoselenocyanates 1 react with malononitrile (6a) and propargyl chloride (8) in DMF in the presence of Et3N to give the corresponding 2-(3-aryl-2,3-dihydro-4-methyl-1,3-selenazol-2-ylidene)malononitriles 12 as major products. The analogous
- Sommen, Geoffroy L.,Linden, Anthony,Heimgartner, Heinz
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body text
p. 209 - 219
(2009/02/07)
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- One-pot synthesis of 2-imino-1,3-selenazolidines by reaction of isoselenocyanates with propargylamine
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One-pot synthesis of 2-imino-5-methylene-1,3-selenazolidines has been achieved by reactions of alkylisoselenocyanates with propargylamines in high yields. 1H NMR and NOESY experiments were used to explain the selenium coupling with hydrogen of
- Koketsu, Mamoru,Sakai, Tsutomu,Kiyokuni, Takashi,Garud, Dinesh R.,Ando, Hiromune,Ishihara, Hideharu
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p. 1607 - 1615
(2007/10/03)
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- Synthesis of 5-selenoxo-1,2,4-triazole-1-carboxylates from isoselenocyanates and azodicarboxylates
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A mixture of an azodicarboxylate and triphenylphosphine in dichloromethane reacted with aryl isoselenocyanates (1) at room temperature to give 4,5-dihydro-5-selenoxo-1H-1,2,4-triazole-1-carboxylates (4a-f) in a one-pot reaction in good to excellent yields
- Favero, Francesco,Sommen, Geoffroy L.,Linden, Anthony,Heimgartner, Heinz
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p. 749 - 762
(2007/10/03)
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- Synthesis of 4-(phenylamino)quinazoline-2(1H)-selones and diselenides from isoselenocyanates: Dimroth rearrangement of an intermediate
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The reaction of anthranilonitriles 8 with phenyl isoselenocyanates (1a) in dry pyridine under reflux gave 4-(phenylamino)quinazoline-2(1H)-selones 9 (Scheme 2). They are easily oxidized and converted to diselenides of type 11. The analogous reaction of 8a
- Atanassov, Plamen K.,Linden, Anthony,Heimgartner, Heinz
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p. 1873 - 1887
(2007/10/03)
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- Synthesis of O-unprotected glycosyl selenoureas. A new access to bicyclic sugar isoureas
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β-D-Gluco and mannopyranosyl selenoureas have been prepared by coupling of the corresponding glycosylamines with phenyl isoselenocyanate in aqueous pyridine. Alkyl and aryl isoselenocyanates, and 1,4-phenylene diisoselenocyanate have been obtained from the corresponding formamides with an excess of triphosgene, black selenium and triethylamine. Treatment of the O-unprotected β-D-glucopyranosyl selenourea with aqueous oxygen peroxide afforded a 1,2-trans-fused bicyclic isourea.
- Fernández-Bola?os, José G.,López, óscar,Ulgar, Víctor,Maya, Inés,Fuentes, José
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p. 4081 - 4084
(2007/10/03)
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- Synthesis of 3-acetyl-N-aryl-4-diethylaminoselenet-2(2H)-imines from 4-diethylamino-3-butyn-2-one and aryl isoselenocyanates
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The reaction of aryl isoselenocyanates (1a-d) with 4-diethylamino-3-butyn-2-one (6) in refluxing tetrahydrofuran afforded N-arylselenet-2(2H)-imines (7) in moderate yields. The structure of the stable 4-bromophenyl derivative (7b) has been established by
- Atanassov, Plamen K.,Linden, Anthony,Heimgartner, Heinz
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p. 521 - 533
(2007/10/03)
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- An efficient and convenient route to some isoselenocyanates via reaction of formamides with bis(trichloromethyl)carbonate and selenium
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A class of isoselenocyanates was synthesized via one-pot procedure of N-substituted formamides with selenium and bis(trichloromethyl)carbonate in the presence of triethylamine in good yields.
- Su,Liang
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p. 645 - 647
(2007/10/03)
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- Selenium-containing heterocycles from isoselenocyanates: Synthesis of 1H-5-selena-1,3,6-triazaaceanthrylene derivatives
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The reaction of aryl isoselenocyanates 8 with methyl 3-amino-4-chloro-1-ethylpyrrolo[3,2-c]quinoline-2-carboxylate (6) in boiling pyridine leads to tetracyclic selenaheterocycles of type 9 in high yield (Scheme 3). A reaction mechanism via an intermediate
- Atanassov, Plamen K.,Linden, Anthony,Heimgartner, Heinz
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p. 3235 - 3243
(2007/10/03)
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- Selenium-containing heterocycles from iso-selenocyanates: Synthesis of 2-arylamino-selenazolo[5,4-b]pyridines
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The reaction of 3-amino-2-chloropyridine (4) with aryl isoselenocyanates (2a-d) in refluxing 2-propanol gave the hydrochlorides of 2-arylaminoselenazolo[5,4-b]pyridines (7a-d) in good yield. The free bases (8a-d) were obtained after treatment with aqueous NaOH and recrystallization. A reaction mechanism via the intermediate selenourea derivatives (5) is most likely. The structure of the 2-phenylamino derivative (8a) has been established by X-Ray crystallography.
- Atanassov, Plamen K.,Linden, Anthony,Heimgartner, Heinz
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p. 569 - 579
(2007/10/03)
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- A Convenient and High Yielding Procedure for the Preparation of Isoselenocyanates. Synthesis and Reactivity of O-Alkylselenocarbamates.
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A high yielding one pot procedure for the preparation of isoselenocyanate from the corresponding formamide is reported.Various aromatic and aliphatic primary amines were employed in order to prepare the isoselenocyanates to establish the generality of the procedure.O-Alkylselenocarbamates of various primary, secondary and tertiary alcohols were synthesized and their stability and comparative reactivity were studied.Radical deoxygenation of the selenocarbamate of a secondary and a tertiary alcohol was accomplished under various conditions.
- Barton, Derek H. R.,Parekh, Shyamal I.,Tajbakhsh, Mahmoud,Theodorakis, Emmanouil A.,Tse, Chi-Lam
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p. 639 - 654
(2007/10/02)
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- α,β-UNSATURATED THIOLATES AND THEIR ANALOGS IN CYCLOADDITION REACTIONS XVI. REACTION OF 2-ARYLETHYNETHIOLATE SALTS WITH PHENYL ISOSELENOCYANATE
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Potassium 2-arylethynethiolates enter into cyclization with phenyl isoselenocyanate at the C=Se bond with the formation of the products from 1,3-anionic cycloaddition, i.e., 2-phenylimino-4-aryl-1,3-thiaselenoles.The reaction is accelerated by donating su
- Zmitrovich, N. I.,Petrov, M. L.,Petrov, A. A.
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p. 1219 - 1222
(2007/10/02)
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- α,β-UNSATURATED THIOLATES AND THEIR ANALOGS IN CYCLOADDITION REACTIONS. XV. REACTION OF 2-ARYLETHYNESELENOLATES WITH PHENYL ISOSELENOCYANATE
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Potassium 2-arylethyneselenolates enter into cyclization with phenyl isoselenocyanate to form the products from 1,3-anionic cycloaddition, i.e., 2-phenylimino-4-aryl-1,3-diselenoles.Donating substituents accelerate and accepting substituents retard this reaction.If the potassium is substituted by lithium, the yield of the cyclization products is substantially reduced. 2-Phenylimino-4-aryl-1,3-diselenoles are converted by treatment with methyl iodide into 2-(N-methylphenylamino)-4-aryl-1,3-diselenolium iodides, which form 4-aryl-1,3-diselenole-2-selenones under the influence of hydrogen selenide.
- Zmitrovich, N. I.,Petrov, M. L.,Petrov, A. A.
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p. 154 - 157
(2007/10/02)
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- Transition metal complexes of the selenium analogs of 2-acetyl- and 2-propionylpyridine thiosemicarbazones useful for treating malarial infections and leukemia
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This invention relates to novel transition metal complexes of 2-acetyl- and-propionylpyridine thiosemicarbazones, their selenium analogs. These compounds are useful as antimalarial and antileukemic agents. Also disclosed are several synthetic procedures u
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- 2-acetyl- and 2-propionylpyridine selenosemicarbazones
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This invention relates to novel 2-acetyl- and 2-propionylpyridine selenosemicarbazones. These compounds are useful as antimalarial and antileukemic agents. Also disclosed are several synthetic procedures used to prepare the selenosemicarbazones.
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