India's research output in organic chemistry journals ranks third after China and the USA. Recent research activities in India have made notable contributions to the areas of total synthesis, natural product isolation, heterocycle synthesis, asymmetric metal- and organocatalysis, sequential one-pot reactions, C–H activation, C–C coupling reactions, click chemistry, photocatalysis, nanocatalysis, supramolecular and bioorganic chemistry. In 2016, for the first time, India's relative citation impact (average citations per article in each year, weighted by the world average) was higher than average.

With this background, we intend to provide the reader with a flavour of research highlights and recent trends in chemical research performed in India by the young organic chemistry community (≤45 years).

This virtual issue, initiated by our new Advisory Board member Dhevalapally B. Ramachary, University of Hyderabad, combines Communications, Full Papers, and Microreviews published in Eur. J. Org. Chem. in the second half of 2017, showcasing the state of the art in organic chemistry in India.

Golam Kibriya, Sadhanendu Samanta, Mukta Singsardar, Sourav Jana, Alakananda Hajra*

The metal-free sodium persulfate mediated direct selenylation of arenofurans is achieved at room temperature, and the products are obtained in high yields. The reaction is applicable to a variety of naphthofurans, benzofurans, and furocoumarins. The reaction proceeds through an electrophilic substitution pathway.

Eur. J. Org. Chem. 2017, No. 21, 3055–3058 [Communication]

Shivangi Sharma, Pravin Kumar, Arun Sharma, Rama Krishna Peddinti*

Benzoxazines incorporating a vinylogous carbamate functionality have been derivatized under mild conditions with arylthiols or N-arylmaleimides to form hybrid structures with potential biologically activity.

Eur. J. Org. Chem. 2017, No. 21, 3059–3071 [Full Paper]

Greeshma Gopalan, Bhandara Purayil Dhanya, Jayaram Saranya, Thankappan Remadevi Reshmitha, Thekke Veettil Baiju, Murugan Thulasi Meenu, Mangalam S. Nair, Prakasan Nisha*, Kokkuvayil Vasu Radhakrishnan*

The reaction of zerumbone with sulfonamides through a one-pot, metal-free synthetic strategy involving the use of iodosobenzene diacetate as the oxidizing agent furnishes zerumbone–aziridine derivatives. We also performed antiproliferative and antidiabetics screenings of the synthesized compounds.

Eur. J. Org. Chem. 2017, No. 21, 3072–3077 [Communication]

Basuli Suchand, Gedu Satyanarayana*

A simple KOtBu-mediated synthesis of functionalized ketones through domino internal hydrogen transfer and functionalization of allylic alcohols is reported.

Eur. J. Org. Chem. 2017, No. 26, 3886–3895 [Full Paper]

Atanu Modak, Sujoy Rana, Ashwini K. Phukan*, Debabrata Maiti*

The mechanistic details of palladium acetate catalyzed deformylation reactions are outlined herein. On the basis of kinetic studies, competition experiments, and a Hammett study, a plausible catalytic cycle is proposed. From heterogeneity tests, the existence of homogeneous and heterogeneous pathways is suggested. DFT calculations also support the catalytic pathway under homogeneous conditions.

Eur. J. Org. Chem. 2017, No. 28, 4168–4174 [Full Paper]

Suvankar Debbarma, Modhu Sudan Maji*

A new synthetic route for the construction of amide C–N bonds by chelation-assisted Cp*RhIII-catalyzed C–H bond functionalization has been developed. This allows an easy access to starting precursors for the synthesis of 4H-benzoxazin-4-one derivatives.

Eur. J. Org. Chem. 2017, No. 25, 3699–3706 [Full Paper]

Bhavani Shankar Chinta, Beeraiah Baire*

The first synthetic approach to a spirobionaphthalene natural product is reported. Rapid synthesis of the functionalized [5-5-6-6] tetracyclic framework in spiropreussione B is achieved by employing a tetradehydro-Diels–Alder reaction between an enyne and an alkyne as the key step.

Eur. J. Org. Chem. 2017, No. 24, 3457–3460 [Communication]

P. Pon Sathieshkumar, Penchala Latha, Rajagopal Nagarajan*

The protecting-group-free total synthesis of pseudellone C is achieved for the first time on a gram scale with an overall yield of 44 % from economic and commercially available starting materials.

Eur. J. Org. Chem. 2017, No. 22, 3161–3164 [Communication]

Santosh J. Gharpure*, Laxmi Narayan Nanda, Dimple Kumari

An enantiospecific total synthesis of (+)-3-epi-epohelmin is described by using a nitrogen-substituted donor–acceptor (D–A) cyclopropane. The chiral cyclopropane is prepared by highly diastereoselective intramolecular cyclopropanation of a vinylogous carbamate. Regioselective ring opening of the D–A cyclopropane and further utilization of the ring-opened product gives 3-epi-epohelmin A.

Eur. J. Org. Chem. 2017, No. 27, 3917–3920 [Communication]

Panduga Ramaraju, Nisar A. Mir, Deepika Singh, Preetika Sharma, Rajni Kant, Indresh Kumar*

The 2-iodoxybenzoic acid (IBX)-mediated oxidative rearrangement of tetrahydropyridine intermediates, prepared through proline-catalyzed annulation between glutaraldehyde and imines, is explored as a means for the regioselective synthesis of pyrrole-2,4-dialdehydes. PMP = 4-MeOC 6 H 4 .

Eur. J. Org. Chem. 2017, No. 24, 3461–3465 [Communication]

Buddhadeb Mondal, Shiny Nandi, Subhas Chandra Pan*

This review summarizes the recent developments in the organocatalytic asymmetric synthesis of tetrahydrothiophenes and tetrahydrothiopyrans. A variety of sulfur-containing compounds have been employed for their preparation.

Eur. J. Org. Chem. 2017, No. 32, 4666–4677 [Microreview]

Abadh Kishor Jha, Nidhi Jain*

Unprecedented copper acetate catalysed and copper-free homocoupling reactions of 2-phenylpyridine N-oxides to yield N,N′-dioxides or N-monoxides in the presence of LiOtBu is reported. The chemoselectivity is governed by oxidative cross-dehydrogenative coupling and S N Ar pathways, respectively.

Eur. J. Org. Chem. 2017, No. 32, 4765–4772 [Full Paper]

Chandan Kumar Shahi, Sajan Pradhan, Aditya Bhattacharyya, Raushan Kumar, Manas K. Ghorai*

2-Arylquinoxalines have been synthesized by an unprecedented CuI-catalyzed ring-opening/cyclization/detosylation/aromatization cascade reaction of activated aziridines with 2-bromoanilines. The regioselective, high-yielding transformation is amenable to a variety of aziridines and 2-bromoanilines. Tyrphostin AG 1296, a PDGF-receptor tyrosine kinase inhibitor, has also been synthesized.

Eur. J. Org. Chem. 2017, No. 24, 3487–3495 [Full Paper]

Lakshmana K. Kinthada, K. Naresh Babu, Dikshaa Padhi, Alakesh Bisai*

Lewis-acid-catalysed reaction of 3-hydroxy-2-oxindoles with a variety of terminal alkynes has been demonstrated to give2-oxindoles/spiro-fused 2-oxindoles sharing an all-carbon quaternary centre. This reaction presumably goes through intermediate 2H-indol-2-one, which has been proved via some control experiments.

Eur. J. Org. Chem. 2017, No. 21, 3078–3091 [Full Paper]

Raghunath Bag, Pinaki Bhusan De, Sourav Pradhan, Tharmalingam Punniyamurthy*

An overview of recent developments in the vicinal dioxygenation of olefins by radical approaches is presented.

Eur. J. Org. Chem. 2017, No. 37, 5424–5438 [Microreview]

Manickam Bakthadoss*, Polu Vijay Kumar, Tatiparthi Sushmitha Reddy

A protocol for the synthesis of C5-olefinated 2-arylchromanones in a regio- and stereoselective fashion through the ruthenium-catalyzed oxidative coupling of diversified 2-arylchromanones with various alkenes through a keto-directed, site-selective C–H activation reaction is developed. IBO = isobornyl.

Eur. J. Org. Chem. 2017, No. 30, 4439–4444 [Communication]

Popat S. Shinde, Nitin T. Patil*

The gold(III)-catalyzed dehydrazinative coupling of ethynylbenziodoxolones with arylsulfonyl hydrazides allows for the synthesis of alkynyl sulfones. The mild reaction conditions and the tolerance of electron-withdrawing and -donating substituents in the arylsulfonyl hydrazides make this process amenable for gram-scale synthesis of functionalized alkynyl aryl sulfones.

Eur. J. Org. Chem. 2017, No. 24, 3512–3515 [Communication]

Kuppan Ramachandran, Pazhamalai Anbarasan*

An efficient protocol for the cobalt(III)-catalyzed chelation-assisted allylation of arene C–H bonds by employing allyl carbonates as allylating reagents and pyrazoles and pyridines as directing groups is described.

Eur. J. Org. Chem. 2017, No. 27, 3965–3968 [Communication]

Kapil Mohan Saini, Sonu Kumar, Monika Patel, Rakesh K. Saunthwal, Akhilesh K. Verma*

A trifluoroacetic acid promoted step-economical one-pot approach to the synthesis of furo-fused quinoxalines/pyrazines by the reaction of 2,3-dichloroquinoxalines/pyrazines with alkynes is described. The reaction involves a Sonogashira coupling step and a hydroxylation followed by a metal-free 5-endo-dig cyclization. Various substituents are tolerated.

Eur. J. Org. Chem. 2017, No. 25, 3707–3715 [Full Paper]

Riki Das, Gangam Srikanth Kumar, Manmohan Kapur*

This microreview focuses on the role and utility of amides and anilides in directed, proximal C–H bond functionalization reactions.

Eur. J. Org. Chem. 2017, No. 37, 5439–5459 [Microreview]

Shanmugam Sakthivel, Ashish Sharma, Rengarajan Balamurugan*

An efficient synthesis of substituted pyridines through the cyclization of easily accessible N-propargylic α-enamino esters is described. This method involves regioselective addition of propargylamines to alkynyl esters to produce N-propargylic α-enamino esters, which act as the key intermediates in the synthesis.

Eur. J. Org. Chem. 2017, No. 27, 3941–3946 [Communication]

Abhijeet S. Jadhav, Ramasamy Vijaya Anand*

A 100 % atom-efficient continuous-flow protocol to access diarylmethyl thioethers through the triflic acid (TfOH) catalyzed 1,6-conjugate addition of thiols to p-quinone methides by using microreactor technology is developed.

Eur. J. Org. Chem. 2017, No. 25, 3716–3721 [Communication]

Shivaprasad Manchineella, Chandrashekhar Voshavar, Thimmaiah Govindaraju*

Radical-scavenging cyclic dipeptides (CDPs) have been designed and evaluated through structure–activity screening. DOPA-containing CDPs showed superior antioxidant properties that are comparable to the gold standards ascorbic acid and butylated hydroxyanisole. Antioxidant fibrous biomaterial scaffolds were fabricated by electrospinning silk fibroin incorporated with radical-scavenging CDPs.

Eur. J. Org. Chem. 2017, No. 30, 4363–4369 [Full Paper]

Ashik A. Sayyad, Krishna P. Kaliappan*

Sugar-derived enynes undergo a sequence of enyne metathesis followed by Diels–Alder reactions with quinones to give steroid-mimicking sugar–oxasteroid–quinone hybrids. The use of different types of sugar dienes derived from a common precursor leads to three different scaffolds. Thus, a library of hybrid molecules with a steroid backbone or a modified steroidal backbone can be synthesised.

Eur. J. Org. Chem. 2017, No. 34, 5055–5065 [Full Paper]

Alok Ranjan, Abhijit S. Deore, Swapnil G. Yerande, Dattatraya H. Dethe*

Thiol–yne coupling of propargylamine with isothiocyanate has been developed under metal- and solvent-free conditions. The addition of propargylamine to isothiocyanate gives propargylthiourea. This intermediate in situ undergoes intramolecular 5-exo-dig cyclization to give thiazolidin-2-ylideneamine. Wide varieties of thiazolidin-2-ylideneamine derivatives were formed in excellent yields.

Eur. J. Org. Chem. 2017, No. 28, 4130–4139 [Full Paper]

E. Ramesh, Tirumaleswararao Guntreddi, Akhila K. Sahoo*

A modular strategy for the synthesis of 6-substituted 2,3-diarylbenzo[b]thiophenes involving oxidative annulation of (arylthio)phthalimide derivatives with alkynes in the presence of AlCl 3 is developed. The transformation proceeds by oxidative cleavage of the S–N bond and 1,2-sulfur migration and occurs at room temperature.

Eur. J. Org. Chem. 2017, No. 30, 4405–4413 [Full Paper]

Kengadarane Anebouselvy, Kodambahalli S. Shruthi, Dhevalapally B. Ramachary*

Asymmetric supramolecular organocatalysis emerges from many interactions between substrates and catalysts: namely, substrate–catalyst, catalyst–catalyst and substrate–substrate interactions. Here the importance and applications of these interactions in governing both the reactivity and the selectivity of asymmetric organocatalytic reactions as a result of stable pre-transition states are shown.

Eur. J. Org. Chem. 2017, No. 37, 5460–5483 [Microreview]

B. V. Subba Reddy*, Preethi Narayanan Nair, Aneesh Antony, Nikhil Srivastava

Application of the Prins cyclization to the synthesis of spirocylic networks has made substantial progress recently. Spiro motifs are found in many natural products with promising biorelevance and are increasingly being incorporated in drug candidates. Further, various spirocyclic chiral ligands have shown promise in asymmetric synthesis.

Eur. J. Org. Chem. 2017, No. 37, 5484–5496 [Microreview]

Mahesh S. Kutwal, Chandrakumar Appayee*

Perfect regioselectivity is achieved in the γ-alkylation of linear α,β-unsaturated aldehydes in the presence of trifluoroethanol (TFE). Furthermore, in situ kinetic resolution is demonstrated for enantioenrichment of the γ-alkylated products. Together, the activation of electrophiles by TFE and in situ kinetic resolution allow excellent selectivity in dienamine catalysis to be realized.

Eur. J. Org. Chem. 2017, No. 29, 4230–4234 [Communication]

Nagnath Yadav More, Masilamani Jeganmohan*

The cross-coupling of substituted phenols or naphthols with substituted aromatics in the presence of K 2 S 2 O 8 and Bu 4 N+·HSO 4 – in CF 3 COOH at ambient temperature is described. The cross-coupling reaction provides unsymmetrical biaryls in good to moderate yields in a highly regioselective manner. A possible reaction mechanism was proposed and supported by UV/Vis and EPR studies.

Eur. J. Org. Chem. 2017, No. 29, 4305–4312 [Full Paper]

Srinivasarao Yaragorla*, Abhishek Pareek, Ravikrishna Dada, Pyare Lal Saini

A single-step approach to the synthesis of 3-iodoquinolines has been achieved through a regioselective iodocyclization. The synthesis began from readily available materials in an aqueous ethyl acetate medium and was promoted by KOtBu and I 2 at room temperature. Various cross-coupling reactions were used to demonstrate the synthetic utility of the products.

Eur. J. Org. Chem. 2017, No. 31, 4600–4608 [Full Paper]

Nagaraju Barsu, Balakumar Emayavaramban, Basker Sundararaju*

An efficient and atom-economical method for C–H bond alkylation with activated olefins by using air-stable Cp*CoIII catalysts is developed. The reaction proceeds through an M–alkyl intermediate after migratory insertion, and this intermediate undergoes protodemetalation to give the expected alkylated product. DG = directing group.

Eur. J. Org. Chem. 2017, No. 30, 4370–4374 [Communication]

Bijoyananda Mishra, Sujit Manmode, Ravi Raja Adhikari Panda, Srinivas Hotha*

The synthesis of a linear nonadecaarabinofuranoside fragment of a Mycobacterium tuberculosis cell-wall polysaccharide was accomplished using gold-catalysed glycosylations in a split/react/couple fashion.

Eur. J. Org. Chem. 2017, No. 32, 4794–4802 [Full Paper]

Parameswaran Sasikumar, Bernard Prabha, Sarngadharan Sarath Chand, Maniyamma Aswathy, Murali Madhukrishnan, Preethalayam Preethanuj, Eringathodi Suresh, Florian Jaroschik*, Kokkuvayil Vasu Radhakrishnan*

A Lewis acid catalyzed double hydro(hetero)arylation of alkyl-substituted pentafulvenes to synthesize bisindole-substituted cyclopentenoids is developed. In addition, we also demonstrate a hydroheteroarylation–dehydroxylation reaction of 2-hydroxy-substituted pentafulvenes to afford bisindole derivatives with isoprenyl-substituted cyclopentene moieties.

Eur. J. Org. Chem. 2017, No. 30, 4469–4474 [Full Paper]

Somraj Guha, Imran Kazi, Anuradha Nandy, Govindasamy Sekar*

The reactivity and applications of halogen(I) species in organic synthesis are only little studied. The reactivity of a Lewis-base-coordinated halogen(I) species depends on the interaction between halogen and Lewis base. Noncovalent interactions such as halogen bonding are very helpful for generating stabilized intermediates with tunable reactivity. X = Cl, Br, I.

Eur. J. Org. Chem. 2017, No. 37, 5497–5518 [Microreview]