- Synthesis of 2H-1,4-benzothiazin-3(4H)-ones and 2H-1,4-benzoselenazin-3(4H)-ones with the aid of samarium(II) iodide
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Bis(o-nitrophenyl) disulfides or diselenides were easy to reduce by samarium(II) iodide to produce the active intermediates 2 in situ, which readily react with α-halocarboxylic derivatives to yield the corresponding products 2H-1,4-benzothiazin-3(4H)-ones and 2H-1,4-benzoselenazin-3(4H)-ones, respectively, in moderate to high yields under mild conditions.
- Zhong, Weihui,Zhang, Yongmin
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Read Online
- Iodine mediated oxidative cross-coupling of unprotected anilines and heteroarylation of benzothiazoles with 2-methylquinoline
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Iodine-promoted oxidative C-H/C-H cross-coupling of unprotected anilines and 2-methylquinoline to furnish C4-carbonylated aniline (4-aminophenyl)(quinoline-2-yl) methanones in moderate to good yields has been demonstrated. This work provides the first site-selective approach for the synthesis of free amino groups containing methanones including unprecedented C-H functionalization rather than the N-H functionalization of unprotected anilines via the Kornblum oxidation of 2-methylquinoline. Furthermore, we noticed that the incorporation of KOH under standard conditions provides 2-heteroarylbenzothiazoles from benzothiazoles and 2-methylquinoline in good to excellent yields. These transformations do not require any transition metals or peroxides and tolerate various functional groups such as methoxy, hydroxy, bromo, chloro and nitro groups. Moreover, a plausible mechanistic pathway is proposed.
- Rahim, Abdul,Shaik, Siddiq Pasha,Baig, Mirza Feroz,Alarifi, Abdullah,Kamal, Ahmed
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Read Online
- Natural Product-Mimetic Scaffolds with Privileged Heterocyclic Systems: Design, Synthesis, and Evaluation of Antioxidant Activity of Quinazoquinobenzothiazinones
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(Chemical Equation Presented) Structurally diverse quinazolinoquinolinobenzothiazinones based on rutaecarpine structural framework with hybrid structural features of three medicinally privileged heterocyclic systems has been synthesized as natural product-mimetic scaffolds involving the use of multi-step reaction sequences. The synthesized quinazolinoquinolinobenzothiazinones have been evaluated for their antioxidant and radical scavenging activities.
- Sharma, Kshitija,Khandelwal, Sarita,Samarth,Kumar, Mahendra
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Read Online
- Novel synthesis of benzothiazole by self-redox tandem reaction of disulfide with aldehyde
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A novel methodology for the preparation of benzothiazole derivatives via the reaction of ortho-anilino disulfides with aryl and heteroaryl aldehydes catalyzed by Na2S·9H2O has been developed. The reaction mechanism was investigated by LC-MS and 1H NMR. The disulfide was cleaved firstly by the interchange reaction of the disulfide and metal sulfide, and the resulting thiol reacted in situ with the aldehyde to form the corresponding benzothiazoline. Subsequently, the intermediate benzothiazoline reduced the disulfide to thiol and it was oxidized to benzothiazole. The excess benzothiazoline was oxidized by air and both halves of the disulfide were ultimately converted to the desired benzothiazole.
- Liu, Bo,Zhu, Ning,Hong, Hailong,Han, Limin
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Read Online
- Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles
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A facile and sustainable approach for the amination of benzothiazoles with KSeCN using iodine as the catalyst in water has been disclosed under transition-metal free conditions. The reaction proceeded smoothly to afford various primary 2-amino benzothiazoles in up to 96% yield. A series of control experiments were performed, suggesting a ring-opening mechanism was involved via a radical process. This protocol provides efficient synthesis of primary 2-aminobenzothiazoles
- Chen, Xiran,Fu, Lianrong,Hao, Xin-Qi,Shi, Linlin,Song, Mao-Ping,Zhu, Xinju,Zhu, Yu-Shen
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- Facile syntheses of 3-trifluoromethylthio substituted thioflavones and benzothiophenes via the radical cyclization
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3-CF3S substituted thioflavones and benzothiophenes were achieved via the reactions of AgSCF3 with methylthiolated alkynones and alkynylthioanisoles, respectively, promoted by persulfate. This protocol possesses good functional group tolerance and high yields. Mechanistic studies suggested that a classic two-step radical process was involved, which includes addition of CF3S radical to triple bond and cyclization with SMe moiety.
- Wang, Lu,Wang, Huaiyu,Meng, Weidong,Xu, Xiu-Hua,Huang, Yangen
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supporting information
p. 389 - 392
(2020/03/04)
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- Preparation method of o-aminothiophenol
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The invention provides a preparation method of o-aminothiophenol. The preparation method comprises the following steps: putting o-chloronitrobenzene into sodium methyl mercaptide, and performing heating under the action of a catalyst to carry out a methyl vulcanization reaction so as to prepare o-nitrophenyl dimethyl sulfide; putting o-nitrophenyl thioether into a solvent, and carrying out hydrogenation reduction to prepare o-aminobenzene thioether; and demethylating the o-aminothiophenol under the action of hydrobromic acid to obtain the o-aminothiophenol. The preparation method of o-aminothiophenol has the advantages of high yield and high product purity.
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- Iodine- And TBHP-Promoted Acylation of Benzothiazoles under Metal-Free Conditions
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A simple protocol for the synthesis of 2-acylbenzothiazoles using aryl ketones and benzothiazoles in the presence of I 2and TBHP is described. Acylation of the benzothiazoles is achieved through a sequence involving oxidation of the aryl ketone to an aryl glyoxal, ring-opening of the benzothiazole followed by condensation of the amino group with the aryl glyoxal, cyclization and oxidation. The method avoids the use of metals and toxic solvents. In addition, this protocol has the advantage of broad scope and provides good to excellent product yields.
- Wang, Bin,Zhang, Qianwei,Guo, Zhongqi,Ablajan, Keyume
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p. 3058 - 3064
(2020/08/28)
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- Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes
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An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.
- Kawauchi, Daichi,Noda, Kenta,Komatsu, Yoshiyuki,Yoshida, Kei,Ueda, Hirofumi,Tokuyama, Hidetoshi
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supporting information
p. 15793 - 15798
(2020/10/12)
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- Rh-Catalyzed Asymmetric Hydrogenation of Unsaturated Medium-Ring NH Lactams: Highly Enantioselective Synthesis of N-Unprotected 2,3-Dihydro-1,5-benzothiazepinones
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A straightforward method to prepare 1,5-benzothiazepines was reported. Catalyzed by a Rh/Zhaophos complex, unsaturated cyclic NH lactams with a medium-size ring were hydrogenated smoothly, giving remarkably high enantioselectivities. The sulfur atom in the substrates did not bring an inhibition which was observed with commercially available bisphosphine ligands. This method was successfully applied in the scale-up synthesis of (R)-(-)-thiazesim.
- Yin, Congcong,Yang, Tao,Pan, Yingmin,Wen, Jialin,Zhang, Xumu
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supporting information
p. 920 - 923
(2020/02/04)
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- K2S as Sulfur Source and DMSO as Carbon Source for the Synthesis of 2-Unsubstituted Benzothiazoles
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We describe a three-component reaction of o-iodoanilines with K2S and DMSO that provides 2-unsubstituted benzothiazoles in moderate to good isolated yields with good functional group tolerance. Electron-rich aromatic amines and o-phenylenediamines instead of o-iodoanilines provided 2-unsubstituted benzothiazoles and 2-unsubstituted benzimidazoles with and without K2S under similar conditions. Notably, DMSO plays three vital roles: carbon source, solvent, and oxidant.
- Deng, Guobo,Kuang, Daizhi,Liang, Yun,Yang, Yuan,Yu, Jiangxi,Zhang, Fuxing,Zhu, Xiaoming
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supporting information
p. 3789 - 3793
(2020/06/04)
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- Preparation method of (by machine translation)
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The benzothiazole derivatives are dissociated into o-aminophenylsulfated phenol under the catalysis of copper (II) or copper salt and react under the catalysis of copper or (III), copper salt to give a protected V-oxiracetaine, 2,4 - and the protected V 2 - (2,4 -cetine compound can) be (V) obtained 2 - (2,4 - under the action of) a (V) compound under (2 - the action) - 4 - of a reaction (VI) rate of Ts (dvcetine) (VII): Ts (dvcetine) (VII) (Mg STR9 (I) # STR9#). The synthesis method is easy to obtain, simple in process, low in cost, high in purity and suitable for industrial production. (by machine translation)
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Paragraph 0055-0065; 0067-0071
(2019/11/28)
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- Convenient and efficient synthesis of novel 11: H -benzo[5,6][1,4]thiazino[3,4- a] isoindol-11-ones derived from 2-bromo-(2/3-substitutedphenyl)-1 H -indene-1,3(2 H)-diones
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An unprecedented formation of 11H-benzo[5,6][1,4]thiazino[3,4-a]isoindol-11-ones through a one-step reaction of differently substituted 2-aminobenzenethiols and 2-bromo-(2/3-substitutedphenyl)-1H-indene-1,3(2H)-diones in freshly dried ethanol under reflux conditions has been investigated. This unique transformation probably occurs through an initial nucleophilic substitution followed by ring opening and subsequent intramolecular cyclization. The structures of all the synthesized benzo[1,4]thiazino isoindolinones were established by FTIR, 1H NMR, 13C NMR, HRMS, and X-ray crystallographic analysis. This approach was found to be simple and convenient and provides several advantages such as substantial atom economy, short reaction time and operational simplicity.
- Mor, Satbir,Sindhu, Suchita
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p. 12784 - 12792
(2019/05/10)
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- 2-Arylation/alkylation of benzothiazoles using superparamagneticgraphene oxide-Fe3O4 hybrid material as a heterogeneous catalystwith diisopropyl azodicarboxylate (DIAD) as an oxidant
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In this report, we introduced Graphene oxide-iron oxide (GO-Fe3O4) nanocomposites as a heterogeneous catalyst for arylation/alkylation of benzothiazoles with aldehydes and benzylic alcohols in the presence of diisopropyl azodicarboxylate (DIAD) as an oxidant which exclusively produced 2-aryl (alkyl)-1H–benzothizoles in moderate to excellent yields. The absence of precious metals and toxic solvent, easy product isolation, and recyclability of the GO-Fe3O4 with no loss of activity are notable advantages of this method.
- Khalili, Dariush,Etemadi-Davan, Elham,Banazadeh, Ali Reza
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- SINGLE-STEP SYNTHESIS METHOD OF ARYL THIOL AND APPLICATION THEREOF
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The present invention relates to a single-step synthesis method of aryl thiol, and more specifically, to a method of synthesizing aryl thiol in a single-step by making aryl halide react with alkane dithiol in the presence of a transition metal catalyst. According to the present invention, a single-step synthesis method using the transition metal catalyst, the synthesis method which is capable of synthesizing aryl thiol from aryl halide at a high yield, can be provided. Various aryl halides may be applied to the synthesis method. Further, the synthesis method has advantages that an easily usable reagent may be used, operations are simple, and reactions can be performed under mild conditions. In addition, the synthesized aryl thiol may be used in the synthesis of advanced molecules such as diaryl sulfides and benzothiophenes.COPYRIGHT KIPO 2017
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Paragraph 0032; 0033; 0063; 0067; 0068; 0070
(2017/09/02)
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- Highly efficient synthesis of 2-mercaptobenzothiazole derivatives in water: Metal sulfide-disulfide dynamic interchange reaction
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A convenient and efficient method for the synthesis of 2-mercaptobenzothiazoles from disulfide and CS2 mediated by a metal sulfide in water is described. This synthetic methodology could be used to prepare diverse 2-mercaptobenzothiazole derivatives in good to excellent yields. In this paper, the concept of metal sulfide-disulfide dynamic interchange reaction was put forward. Then the intermediates of the interchange reaction between NaHS and a disulfide were detected by LC-MS, which demonstrated that the S-S bond of the disulfide could be broken by the metal sulfide through the dynamic interchange reaction. In addition, NaHS was eventually transformed into sulfur S8 by the dynamic interchange reaction. Moreover, the underlying mechanism of 2-mercaptobenzothiazole formation is proposed, in which NaHS not only acts as an S-S bond cleaving agent but also as an activator of CS2. As a result, a novel synthetic route for the preparation of sulfur-containing heterocycles from a disulfide is developed.
- Lou, Chunqing,Zhu, Ning,Fan, Ronghua,Hong, Hailong,Han, Limin,Zhang, Jianbin,Suo, Quanling
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supporting information
p. 1102 - 1108
(2017/08/15)
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- Novel ammonium ionic liquids as scavengers for aromatic and heterocyclic amines: Conversion into new pharmacological agents
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The aim of our protocol is to develop new simple, economic and efficient scavengers for primary amines, due to their substantial adverse impacts on environment and human health. In this endeavor, we have designed, successfully synthesized and structurally characterized new salicylaldehyde-tri-nbutylammonium ionic liquids which were investigated as scavengers for diverse aromatic and heterocyclic primary amines in the synthesis of new pharmacologically relevant candidates, imines scavenging product, via Schiff-base-scavenging reaction. The new scavengers exhibited good capture efficiency and can be easily regenerated and reused. The advantages of our scavengers over polymer-supported scavengers are the simplicity, shorter reaction time and real-time monitoring of a model reaction. The biocidal and antitumor activities of the scavenging products revealed a moderate to excellent broad-spectrum antibacterial efficacy, low activity or inactivity as fungicides and different levels of cytotoxicity (weak to excellent) against human breast carcinoma (MCF-7) cells.
- Elshaarawy, Reda F.M.,Mokbel, Wafaa A.,El-Sawi, Emtithal A.
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p. 1123 - 1132
(2016/09/28)
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- Metal-free synthesis of benzothiazoles from disulfides of 2-aminobenzenethiol and carboxylic acid via PCl3-promoted tandem reaction
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A metal-free process for the synthesis of benzothiazoles via PCl3-promoted cleavage/acylation/ cyclization of disulfides and carboxylic acids has been developed. In addition to acting as the acylating reagent which converted carboxylic acids into acyl chlorides, PCl3 also converted disulfides to thiols, which promoted disulfides of 2-aminobenzenethiol reacted with carboxylic acid to produce benzothiazoles. The developed method is applicable to a wide range of carboxylic acids containing different functional groups.
- Du, Guangyan,Zhu, Ning,Han, Limin,Hong, Hailong,Suo, Quanling
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p. 1723 - 1734
(2015/12/12)
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- Copper(II)-Catalyzed Single-Step Synthesis of Aryl Thiols from Aryl Halides and 1,2-Ethanedithiol
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A highly efficient transition metal-catalyzed single-step synthesis of aryl thiols from aryl halides has been developed employing copper(II) catalyst and 1,2-ethanedithiol. The key features are use of readily available reagents, a simple operation, and relatively mild reaction conditions. This new protocol shows a broad substrate scope with excellent functional group compatibility. A variety of aryl thiols are directly prepared from aryl halides in high yields. Furthermore, the aryl thiols are used in situ for the synthesis of more advanced molecules such as diaryl sulfides and benzothiophenes.
- Liu, Yajun,Kim, Jihye,Seo, Heesun,Park, Sunghyouk,Chae, Junghyun
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supporting information
p. 2205 - 2212
(2015/07/27)
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- Phenyliodonium diacetate mediated arylation of benzothiazoles with substituted styrenes
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A metal-free synthesis of 2-arylbenzothiazoles was achieved using phenyliodonium diacetate (PIDA) from benzothiazoles and styrenes or β-nitrostyrenes. This transformation tolerates various functional groups such as methoxy, hydroxy, fluoro, chloro, and nitro groups.
- Kamal, Ahmed,Reddy, N.V. Subba,Prasad
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p. 3972 - 3975
(2014/07/08)
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- Design and synthesis of 2-acylbenzothiazoles via in situ cross-trapping strategy from benzothiazoles with aryl ketones
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An I2/KOH synergistically promoted direct ring-opening aroylation of benzothiazoles with aryl ketones has been discovered. Aryl ketones were seen to act as carbonyl sources to construct 2-acylbenzothiazoles. This reaction could provide an example for the convergent integration of self-labor domino sequences based on an in situ cross-trapping strategy.
- Gao, Qinghe,Wu, Xia,Jia, Fengcheng,Liu, Meicai,Zhu, Yanping,Cai, Qun,Wu, Anxin
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supporting information
p. 2792 - 2797
(2013/04/24)
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- Synthesis of 2-aryl benzothiazoles via K2S2O 8-mediated oxidative condensation of benzothiazoles with benzylamines
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A novel way to synthesize 2-arylbenzothiazoles is described. Reactions of benzothiazoles with diverse benzylamines in the presence of K2S 2O8 and KOt-Bu in DMSO-H2O afforded the desired 2-arylbenzothiazoles in good yields. It is notable that no transition-metal catalyst is needed in this reaction. Compared with other known methods, this method of synthesizing 2-arylbenzothiazoles can be advantageous in cases where substituted benzothiazoles and benzylamines are readily available. Georg Thieme Verlag Stuttgart. New York.
- Yang, Zhiyong,Wang, Anwei,Chen, Xiang,Gui, Qingwen,Liu, Jidan,Tan, Ze,Wang, Hua,Shi, Ji-Cheng
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p. 1549 - 1554
(2013/08/23)
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- Synthesis and antimicrobial activity of 2,4-diaryl-2,3-dihydrobenzo[b][1,4] thiazepines
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A new series of structurally diverse 2,3-dihydrobenzo[b][1,4]thiazepines (2,3-dihydro-1,5-benzothiazepines) with substituted phenyl groups at C(2) and C(4) have been synthesized by reaction of 3-(5-bromo-2-methoxyphenyl)-1- arylpropen-1-ones with 2-aminobenzenethiols. The structures of all the synthesized compounds were confirmed by their analytical and spectral data (IR, 1H NMR, 13C NMR). All the synthesized compounds were evaluated for antibacterial and antifungal activity against a variety of bacterial and fungal strains and interesting results were obtained. Some of the compounds had antibacterial and antifungal activity comparable to that of ciprofloxacin and fluconazole.
- Kumar, Mahendra,Sharma, Kailash,Fogla, Ankur Kumar,Sharma, Kanika,Rathore, Madhu
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p. 2555 - 2564
(2013/07/26)
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- CuI-nanoparticles-catalyzed selective synthesis of phenols, anilines, and thiophenols from aryl halides in aqueous solution
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CuI-nanoparticles-catalyzed selective synthesis of phenols, anilines, and thiophenols from aryl halides was developed in the absence of both ligands and organic solvents. Anilines were formed selectively with ammonia competing with hydroxylation and thiophenols were generated selectively with sulfur powder after subsequent reduction competing with hydroxylation and amination.
- Xu, Hua-Jian,Liang, Yu-Feng,Cai, Zhen-Ya,Qi, Hong-Xia,Yang, Chun-Yan,Feng, Yi-Si
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experimental part
p. 2296 - 2300
(2011/06/17)
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- Fluorescence properties of 5-(5,6-dimethoxybenzothiazol-2-yl)-2′- deoxyuridine (dbtU) and oligodeoxyribonucleotides containing d btU
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We describe the synthesis and photophysical properties of 11 substituted 5-(benzothiazol-2-yl)-2′-deoxyuridine derivatives and oligodeoxyribonucleotides (ODNs) containing 5-(5,6-dimethoxybenzothiazol-2-yl)- 2′-deoxyuridine (dbtU), which was the strongest fluorescent derivative among those prepared. The fluorescence properties of dbtU itself and ODNs containing dbtU show the same tendency of being weaker in both neutral and acidic solution and stronger in basic solution. The ODNs (15mer) containing 16 combinations of 5′-XbtU-3′ and 5′-btUY-3′, where X, Y = A, T, G, or C, were synthesized, and their fluorescence intensity and quantum yield in basic solution were compared. On average, only the ODN with the 5′-G btU-3′ sequence shows a 7.9-fold lower fluorescence intensity than the other sequences. Ab initio calculations of 5′-G btU-3′ and 5′-btUG-3′ as models under basic conditions suggest that the lower fluorescence of the ODN containing the 5′-GbtU-3′ sequence is caused by a wider overlap between stacked guanine (Gua) and btUra than that of the 5′- btUG-3′ sequence and that the HOMO is delocalized not only on btUra but also on Gua.
- Hirose, Wataru,Sato, Kousuke,Matsuda, Akira
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experimental part
p. 6206 - 6217
(2011/12/02)
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- Synthesis of benzimidazolones, benzooxazolones, 2-amino-benzothiazoles from ethyl cyanoformate and o-phenylene Diamines, o-aminophenols, oaminothiophenols Promoted by Lithium Bromide ;
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The lithium bromide mediated condensation of 1-amino-2-heteroaryl substrates with ethyl cyanoformate, to obtain versatile alkylcarbamate protected benzoheteroazolones was studied. This unprecedented reaction could be used to furnish different azolones like 2-benzimidazolones, 2-benooxazolones and 2-amino-thiazoles in good yields. 2011 Bentham Science Publishers Ltd.
- Dekhane, Deepak V.,Pawara, Shivaji V.,Gupta, Sunil V.,Shingareb, Murlidhar S.,Thore, Shivaji N.
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body text
p. 406 - 411
(2012/05/04)
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- Synthesis and antimicrobial activity of structurally flexible heterocycles with the 1,4-thiazine heterosystem
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In this work, 4H-1,4-benzothiazines were synthesized by an efficient synthetic method in a single step involving heterocyclization of substituted 2-aminobenzenethiols with β-ketoester. The structures of the synthesized compounds were confirmed by their analytical and spectral data. The synthesized compounds were evaluated for their antimicrobial activity against bacterial species; E. coli and Bacillus cereus. The synthesized compounds showed significant activity against microorganisms, which can be correlated with the privileged heterocyclic structural scaffolds.
- Sharma, Praveen Kumar,Fogla, Ankur,Rathore,Kumar
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p. 1103 - 1111
(2012/04/17)
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- Optimized Drug Conjugates
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The invention generally relates to optimized drug conjugates.
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- Charge carrier transport properties in liquid crystalline 2-phenylbenzothiazole derivatives
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We synthesized liquid crystalline 2-phenylbenzothiazole derivatives and investigated their charge carrier transport properties by time-of-flight experiments. These materials show less ordered phases such as smectic A, smectic C, and nematic phases at temperature range lower than 100°C, and their mobility was relatively small, from 10-5cm2/Vs to 10 -4cm2/Vs. In addition, the mobility depends on temperature, while it did not depend on electric fields. According to these results, we estimated the eneregy distribution of density of states responsible for condition, σ of Gaussian width, to be 78 ～ 118meV.
- Tokunaga, Keiji,Iino, Hiroaki,Hanna, Jun-Ichi
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scheme or table
p. 241 - 249
(2010/06/16)
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- Color tunable phosphorescent light-emitting diodes based on iridium complexes with substituted 2-phenylbenzothiozoles as the cyclometalated ligands
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Several iridium complexes {iridium(III)bis[2-(3-methoxyphenyl)-1,3- benzothiozolato-N,C2′] acetylacetonate (MeO-BT) 2Ir(acac), iridium(III)bis[2-(2,4-difluorophenyl)-1,3- benzothiozolato-N,C2′] acetylacetonate (2F-BT) 2Ir(acac), and iridium(III)bis[2-(2,4-difluorophenyl)-6-fluoro-1,3- benzothiozolato-N,C2′] acetylacetonate (3F-BT) 2Ir(acac)} having different substituents on 2-phenylbenzothiazole have been synthesized. Several iridium complexes {iridium(III)bis[2-(3- methoxyphenyl)-1,3-benzothiozolato-N,C2′] acetylacetonate (MeO-BT)2Ir(acac), iridium(III)bis[2-(2,4-difluorophenyl)-1,3- benzothiozolato-N,C2′] acetylacetonate (2F-BT) 2Ir(acac), and iridium(III)bis[2-(2,4-difluorophenyl)-6-fluoro-1,3- benzothiozolato-N,C2′] acetylacetonate (3F-BT) 2Ir(acac)} having different substituents on 2-phenylbenzothiazole have been synthesized. The phosphorescent light emitting diodes (PHOLEDs) using these iridium complexes as dopant emitters were fabricated. The experimental results revealed that the emissive colors of PHOLEDs could be finely tuned by suitable modification of the substituents on the 2-phenylbenzothiazole ligands. Furthermore, these iridium complexes show better emissive properties than the known iridium(III)bis(2-phenylbenzothiozolato-N,C2′) acetylacetonate (BT)2Ir(acac).
- Chang, Wei-Chieh,Hu, Andrew Teh,Duan, Jiun-Pey,Rayabarapu, Dinesh Kumar,Cheng, Chien-Hong
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p. 4882 - 4888
(2007/10/03)
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- Facile synthesis of 2H-1,4-Benzothiazin-3(4H)-ketoximes and 2H-1,4-Benzoselenazin-3(4H)-ketoximes promoted by SmI2
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2H-1,4-Benzothiazin-3(4H)-ketoximes and 2H-1,4-benzoselenazin-3(4H)-ketoximes were synthesized by the reductive cyclization of bis(o-nitrophenyl) disulfides or diselenides with aromatic or aliphatic β-nitroethylenes using SmI2 in moderate to good yields under mild conditions.
- Xu, Xiaoliang,Zhang, Yongmin
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p. 3537 - 3543
(2007/10/03)
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- Reductions using LiCl/NaBH4: A rapid and efficient cleavage of organic disulfides to mercaptans
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A practical and novel reagent system LiCl/NaBH4 is used for the reductive cleavage of organic disulfides to mercaptans under mild conditions, in excellent yields.
- Rajaram,Purushothama Chary,Iyengar
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p. 622 - 624
(2007/10/03)
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- A new approach to reductive deprotection of thioethers with a low-valent titanium reagent
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Low-valent titanium mediated cleavage of carbon-sulphur bond is reported. This has resulted in an efficient and mild protocol for the deprotection of allyl/benzyl thioethers under reductive condition and with good yields. Deprotection can be performed regio- and chemo-selectively in the presence of acid, ester and N-benzyl/allyl functionalities and is general for aliphatic and aromatic precursors.
- Shadakshari,Talukdar,Chattopadhyay
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p. 1007 - 1010
(2007/10/03)
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- A novel, practical and highly chemoselective methodology for reduction of disulphides to thiols
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A novel, simple and efficient method for the reduction of disulfides to thiols using In/NH4Cl is described.
- Vidya Sagar Reddy,Venkat Rao,Iyengar
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p. 859 - 862
(2007/10/03)
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- A rapid and efficient cleavage of organic disulfides to mercaptans using ZrCl4/NaBH4
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A practical and cheaper reagent system ZrCl/NaBH4 is used for the reductive cleavage of organic disulfides to mercaptans under mild conditions, in excellent yields.
- Purushothama Chayr,Rajaram,Iyengar
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p. 3905 - 3911
(2007/10/03)
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- Synthesis of some new 1,4-benzothiazines and their anti psychotic activity
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1,4-Benzothiazines (1-28) have been synthesized by treating substituted aminothiophenols with various substituted β-diketones in the presence of piperidine in THF solution.
- Chaudhari,Shinde,Shingare
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p. 1250 - 1256
(2007/10/03)
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- Fiber reactive anthraquinone dyes
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Fiber reactive dyes of the anthraquinone type which provide brilliant violet colors without metal complexing. These dyes may be represented by the formula: STR1 wherein W is selected from NR2 and oxygen; R is independently selected from hydrogen, C1 -C6 alkyl; C1 -C6 alkoxy, sulfo and carboxy; R1 is selected from hydrogen, C1 -C6 alkyl and phenyl; R2 is selected from hydrogen and C1 -C6 alkyl; R3 is selected from hydrogen, and C1 -C4 alkyl; n is an integer of 1 or 2; and Y is CH=CH2, or CH2 CH2 Z wherein Z is a group capable of being split off by the action of an alkali reagent.
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- PYRIMIDO-BENZOTHIAZINES
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This invention relates to novel pyrimido-benzothiazine derivative compounds. The compounds of the present invention inhibit the action of the lipoxygenase enzyme and are useful in the treatment or alleviation of inflammatory diseases, allergy and cardiovascular diseases in mammals. this invention also relates to pharmaceutical compositions comprising such compounds.
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- REACTION OF 2-MERCAPTOBENZOTHIAZOLE WITH DIAMINES. SYNTHESIS OF O-AMINOBENZENETHIOL
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Heating of 2-mercaptobenzothiazole in an excess of hydrazine, ethylenediamine or propylenediamine leads to o-aminobenzenethiol.Moreover, with ethylenediamine, ethylenethiourea is isolated as secondary product.Successive addition-elimination steps rationalize these results. Key words: 2-mercaptobenzothiazole; o-aminobenzenethiol; hydrazine; diamines.
- Adelaere, Bruno,Masson, Serge,Vallee, Yannick,Labat, Yves
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p. 173 - 178
(2007/10/02)
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- Organo-metal compositions, preparation and use
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Complexes of a transition metal and a tetrasubstituted aromatic compound which contain at least two transition metal atoms. At least two of the substituents are -SH groups, the other two substituents being -SH, -OH and -NHR. The complexes are prepared by reacting the tetrasubstituted aromatic compound with a transition metal compound in the presence of a disubstituted aromatic compound. Depending on the relative proportions of the di- and tetra--substituted compounds, the resulting complex may contain more than one residue from the tetra-substituted compound and more than two transition metal atoms. The complexes possess infra-red absorbing properties which vary in dependence on the particular complex, the complexes with more than one residue from the tetrasubstituted compound absorbing radiation of longer wavelength. The compounds can be used to provide infra-red absorbing compositions, for example as a coating or inter-layer for glass. The complexes may be used together with one or more different infra-red absorbing materials. The tetra-substituted aromatic compound may be a tetra-thiol and this can be prepared from an aromatic compound containing at least four halogen substituents by reaction with an alkaline thiol compound in the presence of iron and sulphur in a polar solvent such as dimethyl formamide.
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- A Convenient and General Synthesis of 2-Aryl- and 2-Pyridyl-3-oxo-3,4-dihydro-2H-1,4-benzothiazines
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The reaction of bis(2-aminophenyl) disulphide 1 with methyl or ethyl aryl- or pyridylacetates and sodium hydride gives the title compounds in good yield and high purity.The reaction is general, the starting materials easily available and the workup is simple and rapid.
- Jacobsen, Niels,Kolind-Andersen, Hans
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p. 911 - 914
(2007/10/02)
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- REDUCTIVE CLEAVAGE OF SULFUR OF SULFUR-SULFUR BONDS WITH SODIUM HYDROGEN TELLURIDE
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Sodium hydrogen telluride is shown to be an effective reagent for reduction of alkyl, aryl and functionally substituted disulfides to thiols in good yield under mild conditions.Organic thiosulfites (Bunte salt) also give thiols through the corresponding disulfide on reaction with sodium telluride.
- Kong, Fangming,Zhou, Xunjun
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p. 3143 - 3150
(2007/10/02)
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- Reissert Compound Formation with Fused Five-Membered Ring Heterocycles
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Reissert compounds have been prepared in high yield from benzothiazole by use of trimethylsilyl cyanide as source of cyanide in a single phase system.Analogues have been made from benzoxazole, indazole and 1-methylindazole but the method was unsuccessful with 1,2-benzisoxazole and pyrazole.Conjugate base alkylation followed by removal of the Reissert grouping provides a route to 2-alkylbenzothiazoles and -benzoxazoles, and 3-alkylated indazoles.Efficient access to pyridobenzothiazole and benzothiazoloisoquinoline derivatives results from appropriate intramolecular cyclisations.A crystal structure determination of 3-benzoyl-2,3-dihydro-2-benzothiazolecarbonitrile is reported.
- Uff, Barrie C.,Ho, Yee-Ping,Brown, David S.,Fisher, Ian,Popp, Frank D.,Kant, Joydeep
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p. 2652 - 2681
(2007/10/02)
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- Formation of Reissert Analogs from Benzimidazole and Use of Carboxylic Acids in a Retro-Reissert Reaction
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Reissert analogs have been formed in high yields from benzimidazole using trimethylsilyl cyanide and chloroformates.A retro-Reissert reaction can be effected on the products, their carbon-2 alkylated derivatives and benzothiazole analogs, by treatment with hexanoic or benzoic acids.
- Uff, Barrie C.,Ho, Yee-Ping,Burford, Donald L. W.,Popp, Frank D.
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p. 1349 - 1351
(2007/10/02)
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- Pyrolyses of o-Alkoxy- and o-Alkylthio-N-Allylanilines and of Some Related O- and S-Allyl Compounds
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The o-substituted allyl compounds (1)-(12) have been pyrolysed in order to generate aminyl, phenoxyl, and thiophenoxyl radicals with adjacent substituents.In all cases, products are formed by intramolecular hydrogen transfer from the substituent to the radical centre.This process may be followed by rearrangement to give an aldehyde, by heteroatom extrusion to give an alkene, or by ring formation to give five-membered ring heterocycles (Scheme 1, routes A, B1, and B2 respectively.The distribution of products formed by each route is dependent both on the nature of the o-substituent, and on the nature of the initial radical.
- Cadogan, J. I. G.,Hickson, Clare L.,McNab, Hamish
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p. 1885 - 1890
(2007/10/02)
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- 2,4-DIARYL-2,3-DIHYDROBENZOTHIAZEPINES
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2,4-Diaryl-2,3-dihydrobenzothiazepines are obtained in a single stage from chalcones and ortho-aminothiophenol in the presence of triethylamine.The nature of the electronic transitions in their UV absorption spectra is discussed with the use of quantum-chemical methods.It was shown that the seven-membered ring does not invert in the range of temperatures between -80 and +140 deg C and is in the boat form.The main initial event in the fragmentation of the molecules of the obtained compounds under electron impact is the formation of benzothiazole-containing radicalions.In an acidic medium 2,4-diphenyl-2,3-dihydrobenzothiazepine is hydrolyzed to 3-(2-aminophenylthio)-1,3-diphenyl-1-propanone, and in its reaction with 2,4-dinitrophenylhydrazine chalcone hydrazone and o-aminothiophenol are formed.
- Orlov, V. D.,Kolos, N. N.,Ruzhitskaya, N. N.
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p. 1293 - 1297
(2007/10/02)
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- Reaction between 2,2'-Dithiodianiline and Activated Alkynes. Synthesis of 4H-1,4-Benzothiazines
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By the title reaction acetylenic esters (2a-c), ketones (2d-g), and the nitrile (2h) gave in all cases the corresponding 4H-1,4-benzothiazines (3) together with other products whose nature depends on the alkyne used.Thus benzothiazoline and/or benzothiazole, benzothiazepine, and vinylsulphides were obtained in the representative cases (2c, f, h) studied in detail.Some of these latter compounds have been independently synthesised by reaction of 2-aminobenzenethiol with corresponding alkyne (2).In particular conditions by the reactions between 2,2'-dithiodianiline (1) and alkynes (2f, d) we isolated bisenamine compounds (19) and (20) respectively and their intermediacy in formation of the corresponding benzothiazines (3f) and (3d) was achieved.The mechanisms of the observed reactions are also suggested.
- Liso, Gaetano,Trapani, Giuseppe,Reho, Antonia,Latrofa, Andrea,Loiodice, Fulvio
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p. 567 - 572
(2007/10/02)
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