- Structural study involving 9-(pyrid-2-yl)indolizine-1-one and related derivatives of dipyridyl methanol
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For the first time, the synthesis of 9-(pyrid-2-yl)indolizine-1-one from dipyridylpropargyl alcohol together with its molecular structure is reported. As the racemate was used for crystallization, the asymmetric unit contains both enantiomers. The molecular conformation of the pyridyl indolizinone scaffold of the title compound is similar to the one found for the respective chlorophenyl substituted derivative. Furthermore, we report here on the synthesis and X-ray structures of two alkylated dipyridyl methanols, which have been recovered in connection with the synthesis of the indolizinone. Both prochiral alcohols show conformational chirality in the solid state. In both compounds, intramolecular O–H … Npyridine hydrogen bonds stabilizing their molecular conformation are typical. As a common packing motif, we found a O–H?N bonding system featuring the graph set descriptor R2 2(10). With reference to the structural relationship that can be found between pharmaceutically interesting agents and title compounds, the presented molecules are promising models for future drug design.
- Katzsch, Felix,Gruber, Tobias,Schwarzer, Anke,Weber, Edwin
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- Polarographic Behaviour of 2,2'-Dipyridyl-2-pyridylhydrazone (DPPH) and Pyridine-2-aldehyde-2-quinolylhydrazone (PAQH) at the Droping Mercury Electrode
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The polarographic behaviour of 2,2'-dipyridyl-2-pyridylhydrazone (DPPH) and pyridine-2-aldehyde-2-quinolylhydrazone (PAQH) at dme were studied in aqueous Britton-Robinson buffers containing 50percent ethanol.The polograms consist of one irreversible wave in the acidic and alkaline medium.Two electrods are consumed in the splitting of the N-N bond.The effect of pH on the limiting current and E as well as the reduction mechanism are discussed and compared with similar compounds.The values of the kinetic parameters for the electrode reaction at different pH values are also computed from the polarographic results. - Keywords: Electrochemistry; Reduction mechanism; Kinetic parameters
- Zuhri, Ali Z. Abu,Shalabi, Jamal S.
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- Preferential reactivity of pyridylmagnesiumchloride with n,n-dialkyl arylamides over carbonitriles: Synthesis of 2-(Aroyl) pyridines
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Reaction of 2-pyridylmagnesium chlorides with N,N-dialkyl arylamides afford exclusively 2-(aroyl) pyridines in high yields and purity without the formation of any tertiary alcohol. This method employs easily available raw materials and avoids the use of h
- Rao, G. Venkateswara,Swamy, B. Narayana,Kumar, P. Hareesh,Reddy, G. Chandrasekara
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- Transformation Network Culminating in a Heteroleptic Cd6L6L′2Twisted Trigonal Prism
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Transformations between three-dimensional metallosupramolecular assemblies can enable switching between the different functions of these structures. Here we report a network of such transformations, based upon a subcomponent displacement strategy. The flow through this network is directed by the relative reactivities of different amines, aldehydes, and di(2-pyridyl)ketone. The network provides access to an unprecedented heteroleptic Cd6L6L′2 twisted trigonal prism. The principles underpinning this network thus allow for the design of diverse structural transformations, converting one helicate into another, a helicate into a tetrahedron, a tetrahedron into a different tetrahedron, and a tetrahedron into the new trigonal prismatic structure type. The selective conversion from one host to another also enabled the uptake of a desired guest from a mixture of guests.
- Zhang, Dawei,Ronson, Tanya K.,Xu, Lin,Xu, Lin,Nitschke, Jonathan R.
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supporting information
p. 9152 - 9157
(2020/06/27)
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- A Nitrogen-Assisted One-Pot Heteroaryl Ketone Synthesis from Carboxylic Acids and Heteroaryl Halides
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A practical and highly effective one-pot synthesis of versatile heteroaryl ketones directly from carboxylic acids and heteroaryl halides under mild conditions is reported. This method does not require derivatization of carboxylic acids (preparation of acid chlorides, Weinreb amides, etc.) or the use of any additives/catalysts. A wide substrate scope of carboxylic acids with high functional group tolerance has also been demonstrated. The results reveal that the presence of an α-nitrogen on the halide substrate greatly improves the desired ketone formation.
- Demkiw, Krystyna,Araki, Hirofumi,Elliott, Eric L.,Franklin, Christopher L.,Fukuzumi, Yoonjoo,Hicks, Frederick,Hosoi, Kazushi,Hukui, Tadashi,Ishimaru, Yoichiro,O'Brien, Erin,Omori, Yoshimasa,Mineno, Masahiro,Mizufune, Hideya,Sawada, Naotaka,Sawai, Yasuhiro,Zhu, Lei
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p. 3447 - 3456
(2016/05/19)
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- Approaches for the introduction of fluorinated substituents into [1,2,3]Triazolo[1,5-a]pyridines
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[1,2,3]Triazolo[1,5-a]pyridines functionalization with a trifluoromethyl group has been achieved for the first time using different synthetic strategies. Furthermore, these scaffolds have been employed as starting material in the synthesis of new 2,6-disubstituted pyridines containing the trifluoromethyl group, compounds that are not available using other methodologies. A fluorine-mediated triazolopyridine dimerisation is described, improving the previously known synthetic method. Preliminary studies focused on exploring triazolopyridines reactivity with electrophilic fluorine have revealed a new approach for the obtainment of imidazopyridines.
- Chiassai, Leonardo,Adam, Rosa,Drechslerová, Marcela,Ballesteros, Rafael,Abarca, Belén
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- Synthesis of bis(heteroaryl) ketones by removal of benzylic CHR and CO groups
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A copper-catalyzed method for synthesis of diaryl ketones (Ar-CO-Ar′) through removal of benzylic -CH2-, -CO-, and -CHR- groups from Ar-CO-CXR-Ar′ has been discovered. A number of symmetrical and unsymmetrical heterocyclic ketones, which are usually difficult to synthesize, can be prepared in good to excellent yields. This method was applied to the synthesis of the nonsteroidal anti-inflammatory drug suprofen (47 % yield over three steps). Based on preliminary mechanistic and kinetic studies, an active Cu/O2 species is proposed to mediate the rearrangement reaction. Snip snip: A copper-catalyzed method for synthesis of diaryl ketones by removal of benzylic CH2, CO, and CHR groups has been discovered. A number of symmetrical and unsymmetrical heterocyclic ketones, which are usually difficult to synthesize, can be prepared in good to excellent yields. Preliminary mechanistic studies indicate that an active Cu/O2 species mediates the rearrangement. Copyright
- Maji, Arun,Rana, Sujoy,Akanksha,Maiti, Debabrata
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p. 2428 - 2432
(2014/03/21)
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- Ruthenium(II) complexes of multidentate ligands derived from Di(2-pyridyl)methane
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Bis(2,2′-bipyridyl)ruthenium complexes of the model ligand di(2-pyridyl)methane (1) and its multidentate derivatives 1,1,2,2-tetra(2-pyridyl)ethane (2), tetra(2-pyridyl)ethene (3), and hexa(2-pyridyl)[3]radialene (4) have been prepared and characterized by NMR, visible absorption spectroscopy, electrochemical measurements, and, in two cases, by X-ray crystallography. Complexes of (2) and (3) exist as conformationally rigid species with lower than expected symmetry. Ligands (2) and (3) proved surprisingly resistant to forming dinuclear ruthenium complexes. The two diastereoisomeric dinuclear complexes of (4), ΔΛ/ΛΔ and ΔΔ/ΛΛ (rac), are shown to be locked in conformations of C1 and C2 point-group symmetry, respectively. This represents a rare example where the ΔΛ/ΛΔ-dinuclear complex of a achiral, symmetrically bridging ligand is not a meso compound.
- D'Alessandro, Deanna M.,Keene, F. Richard,Steel, Peter J.,Sumby, Christopher J.
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p. 657 - 664
(2007/10/03)
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- TANDEM ORGANOMETALLIC ADDITION REACTIONS TO N-METHOXY-UREAS AND URETHANES IN THE PREPARATION OF UNSYMMETRICAL AND SYMMETRICAL KETONES
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The use of novel reagents 1a-c for the synthesis of ketones in a one pot reaction is described.An interesting leaving group effect was discovered in the fragmentation of the proposed complexes 2 to the intermediate N-methoxyamides 3.
- Hlasta, Dennis J.,Court, John J.
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p. 1773 - 1776
(2007/10/02)
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