TAILIEUCHUNG - Facile synthesis of heteroaryl substituted γ-lactams from nitrovinyl arenes

Aliphatic nitroalkanes with different functional groups were synthesized from the Michael addition reactions of active methylene compounds 2 and nitrovinyl arenes 1 in high yields. The synthesized Michael adducts were subjected to intramolecular cyclization to give heteroaryl substituted γ -lactams in good to high yields under mild reaction conditions. | Turkish Journal of Chemistry Turk J Chem 2018 42 29 35 http chem ITAK c TUB Research Article doi kim-1705-25 Facile synthesis of heteroaryl substituted γ -lactams from nitrovinyl arenes Seda C INAR Canan UNALERO GLU Department of Chemistry Faculty of Science Hacettepe University Ankara Turkey Received Accepted Published Online Final Version Abstract Aliphatic nitroalkanes with different functional groups were synthesized from the Michael addition reactions of active methylene compounds 2 and nitrovinyl arenes 1 in high yields. The synthesized Michael adducts were subjected to intramolecular cyclization to give heteroaryl substituted γ -lactams in good to high yields under mild reaction conditions. Key words γ -Lactam aliphatic nitroalkanes Michael addition nitrovinyl arenes 1. Introduction Nitrogen-containing heterocycles attract chemists due to their utility in medicine. γ -Lactams among N - heterocycles constitute a synthetic challenge because of their important biological activities. 1 For this reason different methodologies have been developed for their synthesis. These methods include ring expansion of β - lactams 2 domino ring opening-cyclization of aziridines 3 intramolecular cyclization 4 5 3 3 cycloaddition 6 7 or radical cyclization reactions. 8 9 The Michael addition reaction of nucleophiles to electron-deficient species serves as a synthetic tool to form a carbon carbon bond within the synthesis of biologically active compounds. Okino et al. used γ - lactam formed from the cyclization of the Michael adduct of diethylmalonate and β -nitrostyrene in the total synthesis of R - - -baclofen. 10 Versatile functionality of the nitro group provides easy transformations into amine 11 12 ketone 13 14 oxime 15 16 or nitrile oxide 17 structures. In this manner nitro functionality-bearing Michael adducts are potential starting materials for the synthesis of biologically active molecules containing γ .

• Hoá học
• Journal of Chemistry
• γ Lactam
• Aliphatic nitroalkanes
• Michael addition
• Nitrovinyl arenes
• Nitrogen containing heterocycles
• Journal of technology and science education
• Innovative chemistry learning model
• Improving the critical thinking skill
• Self efficacy of pre service chemistry teachers
• Pre service chemistry teachers
• SCT learning model syntax covers
• The Chemistry and Antimicrobial Activity of Psychotria reevesii Wall
• The Chemistry and Antimicrobial Activity
• Psychotria reevesii Wall
• The polar fractions against Staphylococcus aureus
• The relationship between teacher related factors
• Students attitudes towards secondary school chemistry subject
• Bureti district Kenya
• Secondary school chemistry subject
• Click chemistry
• Poly(ethylene glycol)
• Poly(epsilon caprolactone)
• Azide functionalized molecules
• Azide montmorillonite clay
• Block copolymer
• Ketene chemistry
• Telechelic polymers
• Controlled radical polymerization (CRP)
• C60 fullerene
• Metallosupramolecular chemistry
• Host–guest complexes
• Supramolecular chemistry
• Donor–acceptor (D–A)
• Ring opening polymerization
• Thiol benzoxazine reaction
• Catechol based benzoxazine copolymer
• Antibacterial coatings
• Benzoxazine chemistry
• Green chemistry
• Heavy metals
• Cetylpyridinium chloride
• Analytical chemistry
• Journal of Science and Technology
• Green organic synthesis of N methylpyrrolidine
• Gas Chromatography Mass spectroscopy
• The green chemistry process
• Via the green chemistry process
• Journal of medical research
• Production of liophilized quality control samples
• Liophilized quality control samples
• Several clinical chemistry test
• Statistical quality control
• Perspectives on blended learning
• The on line platform
• LabLessons for Chemistry
• Hydrogen and Titration
• College mentors alongside
• Contextualizing technology in the classroom via remote access
• Using space exploration themes
• Scanning electron microscopy
• Tools to promote engagement
• Multidisciplinary geology chemistry experiments
• The service of learning chemistry in Industrial Engineering
• Degrees in Industrial Engineering
• Chemical Engineering and Materials Engineering
• The feed back
• Assessment of achievement in problem solving skills
• General Chemistry course
• Problem based learning
• Measure problem solving skills
• Use of chemistry software to teach
• Assess model based reaction and equation knowledge
• Assess model based reaction
• Two advanced placement
• Public suburban high school
• Collaborative activities for solving multi step problems
• Solving multi step problems in general chemistry
• Solving multi step problems
• The relatve partcipaton of instructor students
• Antioxidant activity
• Bioinorganic chemistry
• Cytotoxic activity
• DNA binding and cleavage activity
• Topoisomerase inhibitor
• Transition metal compounds
• Analytical methods
• Electroanalytical chemistry
• Ionic liquids
• Penicillin allergic patients
• Capillary electrophoresis
• Carbamate SCC interactions
• Fluorescence quenching
• Quantum chemistry calculation
• Inhibition chemiluminescence
• Piperazine chemistry
• Structural features
• Anticancer activity
• Anticancer drugs
• D cyclin dependent kinase
• 3 Amino 9 ethylcarbazole
• Multicomponent reaction
• Arylation reactions
• Cyclization reactions
• Pyrrolo[2 3 c]carbazole
• Prido[3 2 b]carbazole
• Ionic liquid
• Organic phase change materials
• Thermal energy storage
• Solvent free medium
• Silicon chemistry
• Reaction mechanism
• Density functional theory (DFT)
• Homogeneous transitionmetal catalysis
• Silicon analogues
• Medicinal chemistry
• Antiproliferative agents
• Protect endangered tissue
• Anti inflammatory cytokines
• Persistent inflammatory reaction
• Formic acid decomposition
• Renewable feedstock
• Energy feedstocks
• High surface area materials