me

A water mediated multicomponent reaction for the synthesis of novel spirooxindole derivatives and their antifungal activity

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00256C, Paper
Min Zhang, Liang Shi, Li Chen, Zhengyu Liu, Ting Zhao, Chunyin Zhu, Liuqing Yang
A total of 27 novel spirooxindoles were synthesized through a water mediated three-component reaction of isatin, 4-aminocoumarin, and 1,3-cyclodicarbonyl compounds. Several compounds showed excellent antifungal activity against Physalospora piricola.
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New 2-pyridone-based donor–acceptor dyes: the effect of the donor group position, type of π-linker and acid–base characteristics of the medium on the photophysical properties

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00177J, Paper
Saveliy P. Sorokin, Mikhail Yu. Ievlev, Oleg V. Ershov
Synthesis of a series of new donor–acceptor dyes based on 2-pyridone and the study of the effect of the position of the donor group, the type of π-linker and the acid–base characteristics of the medium on their photophysical properties.
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Rapid in situ generation of 2-(halomethyl)-5-phenylfuran and nucleophilic addition in a microflow reactor

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00358F, Paper
Open Access
Yuma Matsuura, Shinichiro Fuse
Various 2,5-disubstituted furans were synthesized via 5-substituted 2-halomethylfurans using microflow technology.
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On the mechanism of carboxylate elimination from carbohydrate monoester-derived radicals

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00241E, Communication
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Julia A. Turner, Hendrik Zipse, Mark S. Taylor
Computational analysis of the HAT-induced expulsion of carboxylic acids from monoacylated pyranosides implicates concerted elimination through a hydrogen-bonded transition state.
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Use of ionic liquids in amidation reactions for proteolysis targeting chimera synthesis

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00304G, Paper
Michela Eleuteri, Jenny Desantis, Gabriele Cruciani, Raimondo Germani, Laura Goracci
Selective degradation of disease-causing proteins using proteolysis targeting chimeras (PROTACs) has gained great attention, thanks to its several advantages over traditional therapeutic modalities.
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HFIP-mediated C-3-alkylation of indoles and synthesis of indolo[2,3-b]quinolines & related natural products

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00414K, Paper
Auqib Rashid, Waseem I. Lone, Preeti Dogra, Showkat Rashid, Bilal A. Bhat
An expeditious metal free C-3 alkylation of indoles and its NIS-mediated deviation to indolo[2,3-b]quinolines is reported. Applications of these strategies in accessing bioactive natural products have also been demonstrated.
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A copper-catalyzed asymmetric Friedel–Crafts hydroxyalkylation of pyrazole-4,5-diones with 5-aminoisoxazoles

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00322E, Communication
Siyu Gao, Xiang Sun, Sijie Peng, Zhenggen Zha, Qi Sun, Zhiyong Wang
An asymmetric Friede-Crafts hydroxyalkylation reaction was developed under the catalysis of chiral copper complexes. A variety of pyrazolone derivatives were obtained with excellent yields and enantioselectivities.
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Synthesis of fluorescent 5-heteroarylpyrimidine-containing oligonucleotides via post-synthetic trifluoromethyl conversion

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00402G, Paper
Yuta Ito, Hisato Tanaka, Ayana Murakami, Yasufumi Fuchi, Yoshiyuki Hari
5-(Benzimidazol-2-yl)- and 5-(benzothiazol-2-yl)-pyrimidine bases-modified oligonucleotides were prepared by post-synthetic trifluoromethyl conversion and their fluorescence properties were measured.
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DFT investigation of the DDQ-catalytic mechanism for constructing C–O bonds

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00346B, Paper
Xiu-Fang Zheng, Da-Gang Zhou, Li-Jun Yang
The DDQ-catalytic mechanisms for constructing C–O bonds via H2O and CH3OH as oxygen sources have been investigated with DFT.
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Asymmetric total synthesis of humulane sesquiterpenoids alashanoids B, C, E, and F and 2,9-humuladien-6-ol-8-one

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00393D, Paper
Rasmita Barik, Samik Nanda
Naturally occurring sesquiterpenes having humulane frameworks are structurally intriguing and possess significant biological profiles.
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Structural flexibility of favipiravir and its structural analogues in solutions: experimental and computational insight

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00404C, Paper
Tatiana P. Gerasimova, Almaz A. Zagidullin, Anastasiia N. Nikolaeva, Robert R. Fayzullin, Aliya M. Saitova, Vasili A. Miluykov, Stefan Grimme, Sergey A. Katsyuba
Keto-enol transformations of 6-R-3-hydroxy-2-pyrazinecarboxamides in solutions are accompanied by deprotonation of enol tautomers and the formation of corresponding anionic species. The key factors determining these processes have been identified.
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Catalyst- and base-free visible light-enabled radical relay trihalomethylation/functional group-migration/carbonylation with CX3SO2Cl

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00292J, Paper
Jinkai Hu, Chenglei Yang, Xiaotao Qin, Hui Liu, Tongtong Ma, Ao-tong Shi, Qing-Long Lv, Xingman Liu, Jinhui Yang, Dianjun Li
A visible light-enabled photocatalyst-free radical trihalomethylation/cyano (or benzo[d]thiazol-2-yl) 1,4-migration/carbonylation reaction of 2-hydroxy-2-hex-5-enenitrile (or (benzo[d]thiazol-2-yl)-pent-4-enol) with CX3SO2Cl (X = F, Cl) is reported.
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Reduction of sulfoxides catalyzed by the commercially available manganese complex MnBr(CO)5

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00204K, Paper
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Daniel Leal Lourenço, Ana Cristina Fernandes
A new methodology for the reduction of a wide variety of aliphatic and aromatic sulfoxides catalyzed by the air-stable, cheap and commercially available manganese catalyst MnBr(CO)5 with excellent yields is...
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Covalently linked thieno[2,3-b]thiophene-fullerene dimers: synthesis and physical characterization

Org. Biomol. Chem., 2024, 22,2978-2984
DOI: 10.1039/D4OB00027G, Paper
Abdulrahman M. Alazemi, Mohammad H. BinSabt, Hamad M. Al-Matar, Alan L. Balch, Mona A. Shalaby
Linked thieno[2,3-b]thiophene-fullerene Dimers.
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Asymmetric synthesis of the fully functionalized six-membered A-ring of siphonol A

Org. Biomol. Chem., 2024, 22,2958-2962
DOI: 10.1039/D4OB00104D, Communication
Ying Sun, Shaomin Fu, Bo Liu
The asymmetric synthesis of the fully functionalized six-membered A-ring of siphonol A is presented.
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Recent advances in spirocyclization of maleimides via transition-metal catalyzed C–H activation

Org. Biomol. Chem., 2024, 22,2916-2947
DOI: 10.1039/D3OB01904G, Review Article
Swadhin Swaraj Acharya, Sagarika Patra, Rojalini Maharana, Manaswini Dash, Liza Mama Barad, Bibhuti Bhusan Parida
In recent years, the maleimide scaffold has received a great deal of attention in C–H activation.
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Vinylogous and stereoselective domino synthesis of pyrano[2,3-c]pyrroles from alkylidene meldrum's acids

Org. Biomol. Chem., 2024, 22,2948-2952
DOI: 10.1039/D4OB00233D, Communication
Mariia Savchuk, Giang Vo-Thanh, Sylvain Oudeyer, Hélène Beucher, Jean-François Brière
An expeditious diatereoselective synthesis of pyrano[2,3-c]pyrroles thanks to a domino Vinylogous aza-Michael-Aldol-Cyclocondensation (aza-VMAC) reaction to alkylidene Meldrum's acid derivatives.
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Expanding the scope of the successive ring expansion strategy for macrocycle and medium-sized ring synthesis: unreactive and reactive lactams

Org. Biomol. Chem., 2024, 22,2985-2991
DOI: 10.1039/D4OB00285G, Paper
Open Access
Zhongzhen Yang, Marion Arnoux, Damien Hazelard, Owen R. Hughes, Joe Nabarro, Adrian C. Whitwood, Martin A. Fascione, Christopher D. Spicer, Philippe Compain, William P. Unsworth
New Successive Ring Expansion (SuRE) protocols are described for use on unreactive lactams, as well as iminosugar derived lactams.
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A phosphamide nucleotide analog: a substrate for polymerase synthesis of DNA

Org. Biomol. Chem., 2024, 22,2963-2967
DOI: 10.1039/D4OB00089G, Communication
Jiong Meng, Qiaqia Guo, Xiaona Zhai, Song Yang, Shuai Wang, Pengcheng Wang, Debin Ji
A phosphamide nucleotide analog (dNTPγNH2) exhibited higher stability than dNTPs and can be recognized by DNA polymerases in PCR.
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Stereoselective synthesis of (R)- and (S)-1,2-diazetidine-3-carboxylic acid derivatives for peptidomimetics

Org. Biomol. Chem., 2024, 22,2974-2977
DOI: 10.1039/D4OB00278D, Communication
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Matthew Nutter, Henry Stone, Michael Shipman, Stefan Roesner
Stereoselective synthesis of both enantiomers of orthogonally protected 1,2-diazetidine-3-carboxylic acid (aAze) from homochiral glycidol and its application in peptidomimetics.
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Selective enhancement of (6–4) photoproduct formation in dithymine dinucleotides driven by specific sugar puckering

Org. Biomol. Chem., 2024, 22,3025-3034
DOI: 10.1039/D4OB00279B, Paper
Jouda Jakhlal, Clément Denhez, Stéphanie Coantic-Castex, Agathe Martinez, Dominique Harakat, Thierry Douki, Dominique Guillaume, Pascale Clivio
Evidence is presented that (6–4) photoproduct formation between two thymine residues in dinucleotide analogues is significantly and specifically enhanced when the 5''- and 3''-end sugar puckering are mainly north and south, respectively.
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Photochromism of phenazine-2,3-diol derivatives through excited state intermolecular proton transfer based on keto–enol tautomerization

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00387J, Paper
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Kazuki Ohira, Kumpei Kozuka, Naoki Kaneda, Masahiro Yamamoto, Keiichi Imato, Yousuke Ooyama
It was found that phenazine-2,3-diol derivatives exhibit photochromism through excited state intermolecular proton transfer (ESInterPT) processes based on keto–enol tautomerization.
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BBr3-mediated dearomative spirocyclization of biaryl ynones: facile access to spiro[5.5]dienones

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00274A, Communication
Gaurav Jaiswal, Subhas Chandra Pan
BBr3 mediated dearomative spirocyclization of biaryl ynones has been reported for the direct synthesis of spiro[5.5]dienones with a tri-substituted double bond.
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Nickel-catalysed regio- and stereoselective hydrocyanation of alkynoates and its mechanistic insights proposed by DFT calculations

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00380B, Communication
Shigeru Arai, Koichi Nakazawa, Xiao-Fei Yang, Masaya Nakajima, Shinji Harada, Atsushi Nishida
This work discloses the origin of regio- and stereoselectivity of hydrocyanation of alkynoates.
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Exploring the mechanism of the reductive amination of acetophenones via Borch approach: the role of the acid catalyst

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00160E, Paper
João Pedro Albuquerque Souza, Amanda Krauskopf Jacobs, Leandro Piovan, Renan Borsoi Campos
The energetic viability of several mechanistic variations of the reductive amination of acetophenones via the Borch approach was reexamined through density functional theory calculations. The crucial involvement of the acid...
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Cu(OTf)2/HFIP catalyzed regioselective cycloisomerization of indole-C3-functionalized alkynols to carbazoles

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00421C, Communication
Srinivasarao Yaragorla, Tabassum Khan, Sayonika Chakroborty
We report here a simple and atom economic cycloisomerization reaction of indole-tethered alkynols for constructing diverse carbazoles via 1,2-alkly migration using Cu(OTf)2/HFIP as the excellent promoter system.
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Dess–Martin periodinane-mediated oxidation of the primary alcohol of cytidine into a carboxylic acid

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00240G, Communication
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Alexandra R. E. Serre, Vibhu Jha, Adèle Rivault, Leif A. Eriksson, Goreti Ribeiro Morais, Robert A. Falconer
Herein we describe the first example of the conversion of the primary alcohol of cytidine into a carboxylic acid by use of the Dess–Martin periodinane oxidising agent.
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Electro-oxidative three-component cascade coupling of isocyanides with elemental sulfur and amines for the synthesis of 2-aminobenzothiazoles

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00432A, Paper
Peng-Fei Huang, Jia-Le Fu, Ying Peng, Jian-Hong Fan, Long-Jin Zhong, Kewen Tang, Yu Liu
2-Aminobenzothiazoles are commonly encountered in various functional compounds. Herein, we disclose an electro-oxidative three-component reaction for the effective synthesis of 2-aminobenzothiazoles under mild conditions, utilizing non-toxic and abundant elemental sulfur...
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Revisiting Biginelli-like Reactions: Solvent Effects, Mechanisms, Biological Applications and Correction of Several Literature Reports

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00272E, Paper
Brenno A. D. Neto, Pedro Beck, Arthur Leitão, Yasmin Santana, Jose R. Correa, Carime Vitória da Silva Rodrigues, Daniel Machado, Guilherme Matos, Luciana Machado Ramos, Claudia Cristina Gatto, Carlos Kleber Z. Andrade, Sarah Caldas
This study critically reevaluates reported Biginelli-like reactions using a Kamlet-Abboud-Taft-based solvent effect model. Surprisingly, structural misassignments were discovered in certain multicomponent reactions, leading to the identification of pseudo three-component derivatives...
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Photoproperties of Favipiravir and their 6-Substituted Analogues: Fluorescence Controlled through Halogen Substitution and Tautomerism

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00397G, Paper
Angel H Romero, Marcos Couto, Ivan E Romero, German Fuentes, Matías N. Möller
Herein, we showed the photophysical properties of the favipiravir and their 6-substituted analogues. Also, we interpreted the origin of the fluorescence of the favipiravir and their 6-substituted analogues as function...
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Recent developments in the enzymatic modifications of steroid scaffolds

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00327F, Review Article
Open Access
Huibin Wang, Ikuro Abe
This review highlights the recent advancements in the enzymatic modifications of steroid scaffolds, emphasizing enzymatic hydroxylation, ketoreduction, dehydrogenation, enzymatic cascade reactions, and other modifications.
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Synthesis of Deuteriodifluoromethylthiolated Isocoumarins-1- imines and Isocoumarins Enabled by Multi-Component Reagents System (MCRS)

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00328D, Communication
Xuemin Li, Haofeng Shi, Jiaxin He, Jialiang Wu, Fengxia Sun, Yunfei Du
The combining use of BnSCF2D, mCPBA and Tf2O serves as an efficient multi-component reagents system (MCRS) for the synthesis of deuteriodifluoromethylthiolated isocoumarins-1-imines/isocoumarins via intramolecular cyclization/ deuteriodifluoromethylthiolation of 2-alkynylbenzamide/2-alkynylbenzoates. The approach...
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Natural products from human microbiome: an emergent frontier in organic synthesis and drug discovery

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00236A, Review Article
Goverdhan Mehta, Saumitra Sengupta, Srihari Pabbaraja
Often referred to as “second genome”, human microbiome is at the epicenter of a complex inter-habitat biochemical network, such as the “gut-brain axis”, which have emerged as significant determinant of...
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TEMPO/PhI(OAc)2 promotes the α-aminophosphinoylation of alcohols with amines and H-phosphine oxides in aqueous medium

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00302K, Communication
Qiang Huang, Xin Jin, Lvjia Wu, Jiangdong Li, Qianlu Xing, Xianheng Wang, Changkuo Zhao
The aminophosphinoylation of alcohols with amines and H-phosphine oxides provides an efficient and mild approach to access various α-aminoalkylphosphine oxides in good yields with good tolerance of functional groups using H2O as a clean solvent.
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Measuring local pH at interfaces from molecular tumbling: A concept for designing EPR-active pH-sensitive labels and probes

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00167B, Paper
Open Access
Maxim A. Voinov, Nicholas Nunn, Roshan Rana, Atli Davidsson, Alex I. Smirnov, Tatyana I. Smirnova
EPR-based local pH measurements based on changes in rotational dynamics of spin-bearing molecules upon protonation.
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Regioselective synthesis of 4-arylamino-1,2-naphthoquinones in eutectogel as a confined reaction medium using LED light

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00140K, Communication
R. Vara Prasad, Yogendra Kumar, R. Arun Kumar, Tohira Banoo, Subbiah Nagarajan
The use of a simple carbohydrate-derived eutectogel facilitating a LED-light-induced regioselective synthesis of 4-arylamino-1,2-naphthoquinones in good yields is reported.
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K2CO3-Mediated (3+3-1) Annulation of 1,3-Acetonedicarboxylates with 2-Fluoro-1-nitroarenes: Synthesis of Indoles

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00488D, Paper
Meng-Yang Chang, Chin-Huey Ho, Hsing-Yin Chen
The K2CO3-mediated one-pot reaction of 1,3-acetonedicarboxylates with 2 equiv. of substituted 2-fluoro-1-nitrobenzenes has been developed to synthesize various 2,3-dicarboxylate indoles via a tandem (3 + 3 − 1) annulation pathway....
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DevTools Digest - Chrome 35: Updates to the Developer Tools in Chrome 35

Updates to the Chrome Developer Tools: CSS property quick search, memory stats for heap snapshots, CodeMirror upgrade and more.




me

The Hobbit Experience 2014: Adding WebRTC gameplay to the Hobbit Experience

Learn how North Kingdom built an immersive multimedia experience optimized for modern mobile browsers using Web RTC




me

Tab Discarding in Chrome: a Memory-Saving Experiment




me

The EME Logger extension




me

How long do commercial aircraft last?

What airlines can do to extend the longevity of their fleet




me

A time when hijackings were dime-a-dozen in the US

Unthinkable in today’s hyper-security post-9/11 environment, forced diversions were commonplace in the ’60s




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Domestic air travel leads airline recovery: Boeing

Low-cost carriers aid market with point-to-point structure and affordable rates




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Making a comeback

The aviation industry has proved its resilience by standing strong, despite an unprecedented economic crisis




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Women who fly

The Indian aviation industry must present equal opportunities to both genders




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Domestic airline industry may face a rejig

The pandemic laid bare fault-lines within India’s airlines




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Insolvency of aircraft operator: default remedies.

India should adopt Cape Town Convention as part of the domestic legal framework.




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Sustainable aviation fuels could be a game-changer

But adopting it in Indian aviation could take time




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Regaining momentum during turbulent times

Airlines must find a balances approach to navigating rising fuel costs