Published by: NISCAIR (CSIR)
Indian Journal of Chemistry (Section B) is published by the National Institute of Science Communication and Information Resources (NISCAIR)-CSIR, New Delhi. This journal publishes articles in Organic and Medicinal Chemistry. It includes full length papers, notes and communications and short reviews. The monthly issues covers articles in organic reaction mechanism, theoretical organic chemistry, structure-activity relationships, medicinal chemistry, synthesis of chiral compounds, bio-organic chemistry, enzymes in organic synthesis, reagents in organic synthesis, heterocyclic compounds, phytochemistry (natural products), amino acids, peptides and proteins, spectroscopy in characterization of organic compounds, chemoenzymatic and enantioselective synthesis of organic compounds, synthesis of fullerenes, metal-catalyzed asymmetric reactions, bioactive plant products and combinatorial chemistry.
Dr. P Paravatharajan
ISSN No. : 0376-4699
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Synthesis of 4H-chromene-3,4-dicarboxylate derivatives via an isocyanide-based one-pot three component reaction
Title: Synthesis of 4H-chromene-3,4-dicarboxylate derivatives via an isocyanide-based one-pot three component reaction
Authors: Kumar, Akubathini Shashidhar; Srinivas, Vakiti; Rao, Vedula Rajeswar
Abstract: An efficient one pot three-component reaction method has been developed for the synthesis of dialkyl-5,8-dihydro-6-hydroxy-5,8-dioxo-2-(alkyl/arylamino)-7-undecyl-4H-chromene-3,4-dicarboxylate derivatives by the reaction of embelin, dialkylacetylenedicarboxylates and alkyl/aryl isocyanides. The method when applied to the synthesis of the title compounds give good yields at room temperature with easy reaction work-up. All the synthesized compounds are well characterized by physical and analytical spectral data (IR, 1H and 13C NMR, mass and elemental analyses).
One-pot multi-component synthesis of 4-substituted thiazole Schiff base derivatives and their antibacterial activity
Title: One-pot multi-component synthesis of 4-substituted thiazole Schiff base derivatives and their antibacterial activity
Authors: Deshineni, Rajitha; Velpula, Ravibabu; Ragi, Rajesh; Chellamella, Gyana Kumari
Abstract: A series of 4-substituted thiazole Schiff base derivatives (6a-h, 7a,b and 8a,b) have been synthesized via one pot multi-component condensation of 1-tetralone derivatives with thiosemicarbazide and 4-substituted phenacylbromides/3-(2-bromoacetyl)-2H-chromen-2-one/2-(2-bromoacetyl)-3H-benzo[f]chromen-3-one under conventional heating in absolute ethanol using catalytic amount of acetic acid with good yields. All the synthesized compounds have been characterized by their IR, 1H and 13C NMR, mass spectra and elemental analyses and also assessed for their antibacterial activity against both Gram positive and Gram negative bacterial strains. Compounds 6h, 7a, 7b, 8a and 8b have shown excellent activity against tested bacterial strains when compared to standard drug Gentamicin.
Theoretical and experimental studies of 1,3-dipolar cycloaddition reactions between trimethylsilylazide and citral (geranial and neral)
Title: Theoretical and experimental studies of 1,3-dipolar cycloaddition reactions between trimethylsilylazide and citral (geranial and neral)
Authors: Taban, Sepehr; Taherpour, Avat (Arman)
Abstract: The [3+2] cycloaddition reactions on citral which is the mixture of geranial 1 and neral 2 isomers have been performed to obtain interesting varieties of its derivatives. The probable 1,3-dipolar cycloaddition reactions between citral mixture (1 and 2) with trimethylsilylazide (TMS), the comparison of the citral mixture in the kinetic and thermodynamic reactions, the structural studies of the 1,2,3-triazoline products, carbine reactive intermediates and transition states are investigated. The reactions are studied and discussed by B3LYP/6-31G* method. The main configurations are performed with less steric restraint effects. The HOMO and LUMO orbital levels, ΔΕHOMO-LUMO gaps, dipole moments, Mulliken charges, thermodynamic and kinetic stabilities in vacuum are investigated for the components by the density functional theory (DFT) B3LYP/6-31G* method. The elimination reactions of N2 molecule from the 1,2,3-triazolines to produce aziridine products, the mechanisms, the biradical intermediates and the related transition states have been investigated as well by the use of B3LYP/6-31G* method. Some of the experimental results such as FT-IR, 1H NMR and GC-MS have been carried out in this study to pursue the course of the reactions.
Feasibility and diastereoselectivity of acid-mediated three-component aza-Diels-Alder reactions: Preparation of diversely substituted hexahydro-2H-pyrano [3,2-c]quinolines
Title: Feasibility and diastereoselectivity of acid-mediated three-component aza-Diels-Alder reactions: Preparation of diversely substituted hexahydro-2H-pyrano [3,2-c]quinolines
Authors: Niño, Patricia; Caba, Marta; Aguilar, Nuria; Terricabras, Emma; Albericio, Fernando; Fernàndez, Joan-Carles
Abstract: Synthesis of highly functionalized substituted hexahydropyrano[3,2-c]quinolines 1 in high to moderate yields is described herein. The diastereoselectivity and regioselectivity obtained in the Povarov reactions of dihydropyrans is shown to depend on the nature of the catalytic acid and/or effect of the substitution of the aldehyde reactants used in the Povarov reaction. Thus, Lanthanide Lewis acid catalysts give higher endo diastereoselectivity than protic Brönsted acid catalysts such as trifluoroacetic acid (TFA), 4-nitrophatlic acid (4-NO2PhA) and sulfamic acid (HOTf) which give higher exo diastereoselectivity. Furthermore, it is found that ortho and di-ortho substitution of the aldehyde precursor increased the exo diastereoselectivity which is higher when the bulk of the ortho-group increases. In addition, substitution of the protic Brönsted acid (TFA) for TMSCl catalyst improves the yield of the Povarov reaction maintaining the high exo diastereoselectivity. The procedure allows for scale up of the Povarov reaction and the hexahydropyrano[3,2-c]quinolines can be obtained on a multigram scale.
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