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Rh(III)-Catalyzed regioselective C4 alkylation of indoles with allylic alcohols: direct access to β-indolyl ketones

Org. Biomol. Chem., 2020, 18,3038-3042
DOI: 10.1039/D0OB00396D, Communication
Changduo Pan, Gao Huang, Yujia Shan, Yiting Li, Jin-Tao Yu
A Rh(III)-catalyzed direct C4 alkylation of indoles with allylic alcohols to access β-indolyl ketones was developed.
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Construction of pH sensitive smart glutathione peroxidase (GPx) mimics based on pH responsive pseudorotaxanes

Org. Biomol. Chem., 2020, 18,3125-3134
DOI: 10.1039/D0OB00122H, Paper
Jiaxi Li, Wenlong Jia, Ganghui Ma, Xiaoyin Zhang, Shaojie An, Tao Wang, Shan Shi
Two pH-sensitive smart glutathione peroxidase (GPx) mimics were developed by using pH-responsive pseudorotaxanes based on cucurbit[6]uril and organoselenium compounds.
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C-Glycosylation enabled by N-(glycosyloxy)acetamides

Org. Biomol. Chem., 2020, 18,3043-3046
DOI: 10.1039/D0OB00561D, Communication
Miao Liu, Bo-Han Li, Tian Li, Xia Wu, Meng Liu, De-Cai Xiong, Xin-Shan Ye
An effective C-glycosylation protocol using N-(glycosyloxy)acetamides as donors promoted by SnBr4 has been developed, delivering alkyl C-glycosides and aryl-β-C-glycosides in high yields.
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Experimental results and computational insight into sequential reactions of β-(2-aminophenyl)-α,β-ynones with aryl isocyanates/benzoyl isothiocyanate

Org. Biomol. Chem., 2020, 18,3177-3189
DOI: 10.1039/D0OB00087F, Paper
Antonio Arcadi, Massimiliano Aschi, Marco Chiarini, Fabio Marinelli, Vincenzo Marsicano, Gustavo Portalone
The selective formation of quinazoline vs. benzoxazine  and benzothiazine derivatives from β-(2-aminophenyl)-α,β-ynones and aryl isocyanates/benzoyl isothiocyanate was explored. DFT calculations provide a plausible rationale.
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Construction of 2,3-disubstituted benzo[b]thieno[2,3-d]thiophenes and benzo[4,5]selenopheno[3,2-b]thiophenes using the Fiesselmann thiophene synthesis

Org. Biomol. Chem., 2020, 18,3164-3168
DOI: 10.1039/D0OB00300J, Paper
Roman A. Irgashev, Nadezhda S. Demina, Gennady L. Rusinov
A number of 2,3-disubstituted benzo[b]thieno[2,3-d]thiophenes and benzo[4,5]selenopheno[3,2-b]thiophenes have been obtained using a convenient approach based on the Fiesselmann thiophene synthesis.
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Copper-catalyzed diastereoselective hydrothioetherification of oxa(aza)benzonorbornadienes

Org. Biomol. Chem., 2020, Advance Article
DOI: 10.1039/D0OB00659A, Paper
Qifu Lin, Yongqi Yao, Wen Yang, Yun Tan, Shuqi Chen, Donghan Chen, Dingqiao Yang
A novel copper-catalyzed multicomponent one-pot syn-selective hydrothioetherification of oxa(aza)bicyclic alkenes to synthesize unsymmetrical thioethers has been established.
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Half-sandwich (η5-Cp*)Rh(III) complexes of pyrazolated organo-sulfur/selenium/tellurium ligands: efficient catalysts for base/solvent free C–N coupling of chloroarenes under aerobic conditions

Org. Biomol. Chem., 2020, Advance Article
DOI: 10.1039/D0OB00538J, Paper
Charu Sharma, Avinash Kumar Srivastava, Kamal Nayan Sharma, Raj Kumar Joshi
Three new Rh(III) complexes of organochalcogen (S/Se/Te) ligands were synthesized and along with a co-catalyst Cu(OAc)2, used for the base/solvent free catalysis of Buchwald type C–N coupling of amines and aryl chlorides under aerobic conditions.
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Visible light promoted continuous flow photocyclization of 1,2-diketones

Org. Biomol. Chem., 2020, Advance Article
DOI: 10.1039/D0OB00532K, Paper
Francesco Secci, Stefania Porcu, Alberto Luridiana, Angelo Frongia, Pier Carlo Ricci
A continuous flow Norrish–Yang photocyclization of 1,2-diketones has been developed and applied to the synthesis of functionalized 2-hydroxycyclobutanones, under blue light irradiation.
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Asymmetric trehalose analogues to probe disaccharide processing pathways in mycobacteria

Org. Biomol. Chem., 2020, Advance Article
DOI: 10.1039/D0OB00253D, Paper
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Hadyn L. Parker, Ruben M. F. Tomás, Christopher M. Furze, Collette S. Guy, Elizabeth Fullam
Chemoenzymatic synthesis of azido-functionalised asymmetric trehalose analogues that are resistant to enzymatic degradation to probe carbohydrate processing pathways in mycobacteria.
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Acylation of oxindoles using methyl/phenyl esters via mixed Claisen condensation – An access to 3-alkylideneoxindoles

Org. Biomol. Chem., 2020, Accepted Manuscript
DOI: 10.1039/D0OB00789G, Communication
Ramdas Sreedharan, Purushothaman Rajeshwaran, Pradeep Kumar Reddy Panyam, Saurabh Yadav, C. M. Nagaraja, THIRUMANAVELAN GANDHI
Predominantly, aggressive acid chlorides and stoichiometric coupling reagents are employed in the acylating process for synthesizing carbonyl tethered heterocycles. Herein, we report simple acyl sources, viz. methyl and phenyl esters...
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Recent Progress on Transition Metal-catalysed Regioselective C–H Transformations Based on Noncovalent Interactions

Org. Biomol. Chem., 2020, Accepted Manuscript
DOI: 10.1039/D0OB00703J, Review Article
Yoichiro Kuninobu, Takeru Torigoe
Transition metal-catalysed C–H transformations are powerful tools to obtain functionalised organic molecules from simple starting materials. To control regioselectivity is one of the most important issues in C–H transformations. Since...
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Synthesis of Glycosyl Sulfoximines by a Highly Chemo- and Stereoselective NH- and O-Transfer to Thioglycosides

Org. Biomol. Chem., 2020, Accepted Manuscript
DOI: 10.1039/D0OB00647E, Paper
Arianna Tota, Claudia Carlucci, Luisa Pisano, Giuliano Cutolo, Guy James Clarkson, Giuseppe Romanazzi, Leonardo Degennaro, James A Bull, Patrick Rollin, Renzo Luisi
A synthesis of unprecedented and stable glycosyl sulfoximines is reported. The developed strategies represent the first examples of highly stereoselective sulfoximine formation directly from thioglycosides. X-ray analysis confirmed the structure...
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Copper(I)/Ganphos catalysis: enantioselective synthesis of diverse spirooxindoles using iminoesters and alkyl substituted methyleneindolinones

Org. Biomol. Chem., 2020, Advance Article
DOI: 10.1039/D0OB00546K, Paper
Hao Cui, Ke Li, Yue Wang, Manman Song, Congcong Wang, Donghui Wei, Er-Qing Li, Zheng Duan, François Mathey
A copper/Ganphos-catalyzed asymmetric 1,3-dipolar cycloaddition of glycine iminoesters with alkyl substituted 3-methylene-2-oxindoles is described, producing the spiro[pyrrolidin-3,3'-oxindole]s in good yields with high ee.
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Origin of the ligand effect in the cobalt catalyzed regioselective hydroboration of 1,3-diene

Org. Biomol. Chem., 2020, Advance Article
DOI: 10.1039/D0OB00628A, Paper
Yuhua Liu, ZhongJie Jiang, Jipei Chen
The detailed mechanism and the origin of the ligand-controlled regioselectivity in the cobalt catalyzed hydroboration of 2-substituted 1,3-diene have been investigated.
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Insights into the secondary structures of lactam N-substituted stapled peptides

Org. Biomol. Chem., 2020, Accepted Manuscript
DOI: 10.1039/D0OB00767F, Communication
Aldrin Vasco Vidal, Celia Gonzalez, Stefan Gröger, W Brandt, Jochen Balbach, Carlos Perez, Ludger A. Wessjohann, Daniel G. Rivera
Stapled peptides derived from the Ugi macrocyclization comprise a special class of cyclopeptides with an N-substituted lactam bridge cross-linking two amino acid side chains. Herein we report a comprehensive analysis...
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Protein labeling approach to improve lysosomal targeting and efficacy of antibody–drug conjugates

Org. Biomol. Chem., 2020, 18,3229-3233
DOI: 10.1039/D0OB00265H, Communication
Ying Han, Yifan Da, Mingjia Yu, Yaping Cheng, Xin Wang, Jiale Xiong, Guoying Guo, Yan Li, Xianxing Jiang, Xiaoqing Cai
An anti-EGFR nanobody was labeled at the C-terminus with a lysosome-sorting NPGY (Asn-Pro-Gly-Tyr) motif via sortase-mediated ligation to enhance the clathrin-mediated endocytosis.
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Synthesis, structures and photophysical properties of hexacoordinated organosilicon compounds with 2-(2-pyridyl)phenyl groups

Org. Biomol. Chem., 2020, 18,3239-3242
DOI: 10.1039/D0OB00484G, Communication
Shohei Furuta, Toshiaki Mori, Yusuke Yoshigoe, Kohei Sekine, Yoichiro Kuninobu
We synthesised novel air-, water-, heat-, acid-, and base-stable hexacoordinated organosilicon compounds, which contain two C,N-bidentate ligands and form two silafluorene equivalent moieties, with Lewis acid–base interactions.
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Three-component synthesis of 1,4-benzothiazines via iodide-catalyzed aerobic C–H sulfuration with elemental sulfur

Org. Biomol. Chem., 2020, 18,3234-3238
DOI: 10.1039/D0OB00074D, Communication
Jingjing Jiang, Xiaolong Tuo, Zhuquan Fu, Huawen Huang, Guo-Jun Deng
Five to Six: Beyond the well-established thiazole formation from elemental sulfur, this method provides the first access to the corresponding six-membered N,S-heterocyclic products via direct functionalization of multiple C–H bonds.
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Phenylboronic acid-catalyzed tandem construction of S–S and C–S bonds: a new method for the synthesis of benzyl disulfanylsulfone derivatives from S-benzyl thiosulfonates

Org. Biomol. Chem., 2020, 18,3243-3248
DOI: 10.1039/D0OB00442A, Communication
Raju Jannapu Reddy, Md. Waheed, Gamidi Rama Krishna
A novel and unique phenylboronic acid-catalyzed tandem construction of S–S and C–S bonds via dimerization–sulfonylation has been disclosed for the synthesis of benzyl disulfanylsulfone derivatives.
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The quasi-irreversible inactivation of cytochrome P450 enzymes by paroxetine: a computational approach

Org. Biomol. Chem., 2020, 18,3334-3345
DOI: 10.1039/D0OB00529K, Paper
Emadeldin M. Kamel, Al Mokhtar Lamsabhi
The potency of paroxetine as a P450 inhibitor is mainly attributed to the availability of two active sites on its structure, its compatibility with P450's active site and the ease of its tight coordination to heme iron.
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Direct recognition and sensitive detection of circular RNA with ligation-based PCR

Org. Biomol. Chem., 2020, 18,3269-3273
DOI: 10.1039/D0OB00625D, Communication
Pengbo Zhang, Na Guo, Kejian Gao, Fengxia Su, Fangfang Wang, Zhengping Li
A sensitive and specific method for circRNA detection is developed through the direct ligation of two ingeniously designed DNA probes.
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A domino annulation approach to 3,4-diacylpyrrolo[1,2-a]pyrazines: decoration of pyrazine units

Org. Biomol. Chem., 2020, 18,3324-3333
DOI: 10.1039/D0OB00444H, Paper
Anuradha Dagar, Yohan Seo, Wan Namkung, Ikyon Kim
A new one-pot, sequential three-component access to 3,4-diacylpyrrolo[1,2-a]pyrazine was achieved from the reaction of an α-haloketone, azide, and N-substituted pyrrole-2-carboxaldehyde under mild reaction conditions.
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Modular continuous flow synthesis of orthogonally protected 6-deoxy glucose glycals

Org. Biomol. Chem., 2020, 18,3254-3257
DOI: 10.1039/D0OB00522C, Communication
Subbarao Yalamanchili, Tu-Anh V. Nguyen, Nicola L. B. Pohl, Clay S. Bennett
The use of a continuous flow platform for the rapid and highly efficient construction of differentially protected glycals from commercial sources is described.
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A visible-light-induced “on–off” one-pot synthesis of 3-arylacetylene coumarins with AIE properties

Org. Biomol. Chem., 2020, 18,3346-3353
DOI: 10.1039/D0OB00479K, Paper
Xinjie Wu, Ming Jia, Mengmeng Huang, Jung Keun Kim, Zheng Zhao, Junkai Liu, Jinhu Xi, Yabo Li, Yangjie Wu
A mild one-pot approach to 3-arylacetylene coumarins with potential AIE activities was developed via photosensitizer-free photocatalysis and thermocatalysis.
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Base-promoted 1,6-conjugate addition of alkylazaarenes to para-quinone methides

Org. Biomol. Chem., 2020, 18,3354-3359
DOI: 10.1039/D0OB00419G, Paper
Amritha Rayaroth, Rajat Kumar Singh, Kalyanakrishnan A. V., Krishna Hari, Alagiri Kaliyamoorthy
1,1,2-Triarylethanes embedded with an azaarene unit were prepared in a single step at ambient temperature via the sodium hexamethyldisilazide mediated 1,6-conjugate addition of unactivated alkylazaarenes on para-quinone methides (p-QMs).
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Copper-catalyzed direct amination of benzylic hydrocarbons and inactive aliphatic alkanes with arylamines

Org. Biomol. Chem., 2020, 18,3263-3268
DOI: 10.1039/D0OB00491J, Communication
Hua Yao, Bo Xie, Xiaoyang Zhong, Shengzhou Jin, Sen Lin, Zhaohua Yan
A new synthetic method toward direct C–N bond formation through saturated C–H amination of benzylic hydrocarbons and inactive aliphatic alkanes with primary aromatic amines under an inexpensive catalyst/oxidant (Cu/DTBP) system has been developed.
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Synthesis of α-CF3-substituted E-dehydroornithine derivatives via copper(I)-catalyzed hydroamination of allenes

Org. Biomol. Chem., 2020, 18,3274-3280
DOI: 10.1039/D0OB00580K, Paper
Anna N. Philippova, Daria V. Vorobyeva, Florian Monnier, Sergey N. Osipov
Novel α-CF3-substituted E-dehydroornithine derivatives have been synthesized via the Cu(I)-catalyzed hydroamination of α-CF3-α-allenyl-α-aminocarboxylates/phosphonates with different amines.
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Dipyrazolodioxadiazocines as shelf-stable “ready-to-use” precursors for an in situ generation of enolate-iminium 1,4-dipoles: a straightforward atom-economical approach to pyrazolo[5,1-d][1,3,5]dioxazines

Org. Biomol. Chem., 2020, 18,3382-3391
DOI: 10.1039/D0OB00451K, Paper
Vladimir E. Zhulanov, Valeria A. Vigovskaya, Maksim V. Dmitriev, Pavel S. Silaichev, Andrey N. Maslivets, Michael Rubin
Generation of cyclic enolate-iminium 1,4-dipoles via thermolysis of dipyrazolodioxadiazocines in the presence of ketones allowed for efficient preparation of pyrazolo[5,1-d][1,3,5]dioxazines.
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Correction: Synthetic-biology-based discovery of a fungal macrolide from Macrophomina phaseolina

Org. Biomol. Chem., 2020, 18,3392-3392
DOI: 10.1039/D0OB90051F, Correction
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Yohei Morishita, Terutaka Sonohara, Tohru Taniguchi, Kiyohiro Adachi, Makoto Fujita, Teigo Asai
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Controlling the liberation rate of the in situ release of a chemical fuel for the operationally autonomous motions of molecular machines

Org. Biomol. Chem., 2020, Advance Article
DOI: 10.1039/D0OB00669F, Paper
Chiara Biagini, Giorgio Capocasa, Daniele Del Giudice, Valerio Cataldi, Luigi Mandolini, Stefano Di Stefano
Aminolysis of the anhydride of 2-cyano-2-phenylpropanoic acid can be employed to conveniently regulate the liberation rate of the related acid which, in turn, can be used as a fuel for acid–base operated molecular machines.
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Gold(III)-catalyzed azide-yne cyclization/O–H insertion cascade reaction for the expeditious construction of 3-alkoxy-4-quinolinone frameworks

Org. Biomol. Chem., 2020, Advance Article
DOI: 10.1039/D0OB00745E, Paper
Jingjing Huang, Han Su, Ming Bao, Lihua Qiu, Yuanqing Zhang, Xinfang Xu
A gold-catalyzed cascade reaction has been developed, and it provides an expeditious access to 3-alkoxy-4-quinolines and applications in alkaloid synthesis.
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Dienaminodioate based multicomponent reactions with post-benzylic oxidative transformations mediated by DDQ

Org. Biomol. Chem., 2020, Accepted Manuscript
DOI: 10.1039/D0OB00721H, Paper
Jaice Ravindran, Velickakathu Yadhukrishnan, Reghuvaran Asha , Ravi Shankar Lankalapalli
Multicomponent reactions (MCRs) using dienaminodioate with post-benzylic oxidative transformation by DDQ that afforded a diverse array of products is described. An unprecedented rearrangement of 1,2-dihydropyridines (1,2-DHPs), 3CR products, to 2-pyridones...
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Spiroconyone A, a new phytosterol with a spiro [5,6] ring system from Conyza japonica

Org. Biomol. Chem., 2020, Advance Article
DOI: 10.1039/D0OB00666A, Paper
Long-Gao Xiao, Yu Zhang, Hong-Li Zhang, Ding Li, Qiong Gu, Gui-Hua Tang, Qian Yu, Lin-Kun An
The first rearranged phytosterol (spiroconyone A) with an unusual spiro [5,6] ring system and two new TDP1 inhibitors 7 and 10 showing a strong synergistic effect with topotecan were isolated from Conyza japonica.
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Synthesis of gem-difluoroalkenes via nickel-catalyzed allylic defluorinative reductive cross-coupling of trifluoromethyl alkenes with epoxides

Org. Biomol. Chem., 2020, Advance Article
DOI: 10.1039/D0OB00535E, Communication
Xiao-Yu Lu, Run-Chuang Jiang, Jia-Mei Li, Chuang-Chuang Liu, Qing-Qing Wang, Hai-Pin Zhou
A nickel-catalyzed defluorinative reductive cross-coupling of trifluoromethyl alkenes with epoxides has been developed.
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Hierarchical Self-Assembly of Azobenzene Dyad with Inverted Amide Connection into Toroidal and Tubular Nanostructures

Org. Biomol. Chem., 2020, Accepted Manuscript
DOI: 10.1039/D0OB00833H, Communication
Shiki Yagai, Takuho Saito
Inversion of the connectivity of amide groups in foldable azobenzene dyads with chiral side chains, which can self-assemble into toroids and nanotubes, significantly increases the thermal stability of these aggregates....
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Correction: Nickel-catalyzed cyanation of phenol derivatives activated by 2,4,6-trichloro-1,3,5-triazine

Org. Biomol. Chem., 2020, Advance Article
DOI: 10.1039/D0OB90052D, Correction
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Liang Wang, Yaoyao Wang, Jun Shen, Qun Chen, Ming-Yang He
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TN woman seeks Rs 1 cr compensation from AIDS society

A housewife has moved the Madras High Court seeking Rs 1 crore as compensation and a public apology from the Tamil Nadu AIDS Control Society.




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Six held for forceful religious conversion

The arrests came soon after tribals demanded the arrest of those involved in the activity.




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'In Nepal, some street children are controlled by gangs'

An unwanted child, a street urchin, a knife-wielding gang member and a child labourer — Basu Rai endured the vicissitudes of fate. But after his rescue and rehab, he dedicated his life to saving other street children.




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Cos use foreign money for political funding. Isn’t that influencing polls?

A recent Intelligence Bureau (IB) report has claimed that some well-known NGOs are working to stall economic development at the behest of their foreign donors. Activists and rights groups have been up in arms ever since the report was leaked.




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Women suffer sanitation absence most — also impacts economy: Bindeshwar Pathak

One month after the horrific Badaun gang rape exposed how gravely at risk women and minors lacking domestic toilets are.




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Swiss accounts are a diversion. Bulk of black money is right here in India

The scent of 'black money' is in the air again. At the Supreme Court's order, Modi sarkar has set up a Special Investigation Team to look into cases of illegal outflow of money to foreign havens.




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Indian American Christians condemn assassination of Bhatti

Strongly condemning the assassination of Shahbaz Bhatti, the Federation of Indian Christians Organisations of North America appealed to Islamabad to bring the perpetrators of the "dastardly" crime to justice.




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Hindu guru convicted of molesting girls in US

An octogenarian Hindu religious leader, head of a Hindu ashram, one of the largest temples in the US, has been convicted of molesting two young girls.




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Five-year-old Indian becomes millionaire

A five-year-old Indian boy has become a millionaire overnight after winning a lottery at a national bond draw here.




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Indian connection to prince William and Kate Middleton's wedding cake

Had it not been for the encouragement of her Gujarati husband Kishore Patel, Fiona Cairns may have never made the leap from graphic design to luxury baking.




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Coming to UP? You can use your own vehicle

More than 1.48 lakh people registered on the government's Jan Sunwai portal on Thursday, requesting to be brought back to UP from other states that they have been stuck in since the lockdown was imposed.




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Yogi launches app to collect data of migrants




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Covid warriors in Lucknow put duty before family




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Delhi Covid-19 cases mount to 6,318; toll 68

The total number of coronavirus cases in the national capital climbed to 6,318, with 338 new cases and two fresh deaths being reported on Friday, according to the Delhi government authorities.