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One-pot synthesis of chromenylfurandicarboxylates and cyclopenta[b]chromenedicarboxylates involving zwitterionic intermediates. A DFT investigation on the regioselectivity of the reaction.
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TLDR
The reactants, intermediate zwitterions, transition structures, and intermediate products, leading to the final products, were optimized using the B3LYP functional with the 6-31G(d) basis set and the structures of the products were elucidated by 1D and 2D NMR experiments.Abstract:
The reaction of 1:1 zwitterionic intermediates generated in situ from either tert-butylisocyanide or cyclohexylisocyanide and acetylenedicarboxylates with 3-formylchromones is described, whereupon ...read more
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Synthesis, structure-activity relationship of novel substituted 4H-chromen-1,2,3,4-tetrahydropyrimidine-5-carboxylates as potential anti-mycobacterial and anticancer agents.
B. China Raju,R. Nageswara Rao,Pathi Suman,Perumal Yogeeswari,Dharmarajan Sriram,Thokhir Basha Shaik,Shasi V. Kalivendi +6 more
TL;DR: This is the first report assigning in vitro anti-mycobacterial, anticancer and structure-activity relationship for this new class of 4H-chromen-1,2,3,4-tetrahydropyrimidine-5-carboxylates.
Journal ArticleDOI
1,5-Benzoxazepines vs 1,5-benzodiazepines. One-pot microwave-assisted synthesis and evaluation for antioxidant activity and lipid peroxidation inhibition
Constantinos G. Neochoritis,Constantinos A. Tsoleridis,Julia Stephanidou-Stephanatou,Christos Kontogiorgis,Dimitra Hadjipavlou-Litina +4 more
TL;DR: Structural assignments of the new compounds as well as complete assignment of (1)H and (13)C NMR signals have been unambiguously achieved on the basis of the analysis of their (1D and 2D), IR, MS, and elemental analysis data.
Journal ArticleDOI
Synthesis, Reactions and Uses of Isocyanides in Organic Synthesis. An Update
TL;DR: Isocyanides were formally discovered by Gautier1 and Hofmann2 in 1867 but the history of isocyanide chemistry in fact predates this discovery as mentioned in this paper.
Journal ArticleDOI
Synthesis of Heterocycles by Formal Cycloadditions of Isocyanides
TL;DR: This Focus Review aims at mapping this reactivity and at providing insight into the relationship between the various reported reaction partners and the observed reactivity modes.
Journal ArticleDOI
Palladium-catalyzed cycloisomerization and aerobic oxidative cycloisomerization of homoallenyl amides: a facile and divergent approach to 2-aminofurans.
TL;DR: Preliminary mechanistic studies show that peroxide may be a key intermediate for this Pd-catalyzed radical aerobic oxidative cycloisomerization of homoallenyl amides.
References
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Wrightiadione from Wrightia tomentosa.
Lee-Juian Lin,Gulacti Topcu,Hermann Lotter,Nijsiri Ruangrungsi,Hildebert Wagner,John M. Pezzuto,Geoffrey A. Cordell +6 more
TL;DR: A novel isoflavone wrightiadione, was isolated from Wrightia tomentosa and determination of the carbon framework was based on the interpretation of NMR and mass spectral data, and the structure was confirmed by X-ray analysis.
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The First Synthesis of Coniochaetones A and (±)-B: Two Benzopyranone Derivatives
Journal ArticleDOI
Coniothyrione, a chlorocyclopentandienylbenzopyrone as a bacterial protein synthesis inhibitor discovered by antisense technology.
John G. Ondeyka,Deborah L. Zink,Angela Basilio,Francisca Vicente,Gerald F. Bills,Maria Teresa Diez,Mary Motyl,Gabe Dezeny,Kevin M. Byrne,Sheo B. Singh +9 more
TL;DR: The antisense-rpsD gene-sensitized two-plate assay led to the discovery of a novel chlorinated cyclopentandienylbenzopyrone antibiotic, coniothyrione, C14H9ClO6, isolated from Coniothyrium cerealis MF7209.
Journal ArticleDOI
Synthesis of quinolines from 3-formylchromone.
Andrey S. Plaskon,Sergey V. Ryabukhin,Dmitriy M. Volochnyuk,Konstantin S. Gavrilenko,Alexander Shivanyuk,Andrey A. Tolmachev +5 more
TL;DR: A facile and versatile procedure for the synthesis of 3-(2-hydroxybenzoyl)quinolines and 7H-chromeno[3,2-c]quinolin-7-ones was elaborated on the basis of TMSCl-mediated recyclization of 3-formylchromone with various anilines.
Journal ArticleDOI
2-(N-Methylanilino)-3-formylchromone—a versatile synthon for incorporation of chromone moiety in a variety of heterocyclic systems and macrocycles through reactions with bifunctional nucleophiles
TL;DR: The reaction of 2-(N-methylanilino)-3-formylchromones with a number of bifunctional nucleophiles, involving substitution of N-methyl-lino moiety and/or condensations with 3-formedyl function have provided an easy access to a variety of potentially biologically active hetero-annelated chromones, novel macrocycles, and tetradentate ligands having intact chromone moiety as discussed by the authors.