Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

9,10-Dioxa-1,2-diaza-anthracene derivatives from tetrafluoropyridazine.

ABSTRACT: Reaction of tetrafluoropyridazine with catechol gives a tricyclic 9,10-dioxa-1,2-diaza-anthracene system by a sequential nucleophilic aromatic substitution ring annelation process, further extending the use of perfluoroheteroaromatic derivatives for the synthesis of unusual polyfunctional heterocyclic architectures. The tricyclic scaffold reacts with amines and sodium ethoxide providing a short series of functional 9,10-dioxa-1,2-diaza-anthracene systems.

SUBMITTER: Pattison G

PROVIDER: S-EPMC2887278 | biostudies-literature | 2010 May

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

9,10-Dioxa-1,2-diaza-anthracene derivatives from tetrafluoropyridazine.

Pattison Graham G Sandford Graham G Yufit Dmitrii S DS Howard Judith A K JA Christopher John A JA Miller David D DD

Beilstein journal of organic chemistry 20100506

Reaction of tetrafluoropyridazine with catechol gives a tricyclic 9,10-dioxa-1,2-diaza-anthracene system by a sequential nucleophilic aromatic substitution ring annelation process, further extending the use of perfluoroheteroaromatic derivatives for the synthesis of unusual polyfunctional heterocyclic architectures. The tricyclic scaffold reacts with amines and sodium ethoxide providing a short series of functional 9,10-dioxa-1,2-diaza-anthracene systems. ...[more]

PMID: 20563272

Similar Datasets

Developing 9,10-anthracene Derivatives: Optical, Electrochemical, Thermal, and Electrical Characterization.

Project description:Anthracene-based semiconductors are a class of molecules that have attracted interest due to their air stability, planarity, potential for strong intermolecular interactions, and favorable frontier molecular orbital energy levels. In this study seven novel 9,10-anthracene-based molecules were synthesized and their optical, electrochemical, and thermal properties were characterized, along with their single crystal arrangement. We found that functionalization of the 9,10-positions with different phenyl derivatives resulted in negligible variation in the optical properties with minor (±0.10 eV) changes in electrochemical behavior, while the choice of phenyl derivative greatly affected the thermal stability (Td > 258 °C). Preliminary organic thin film transistors (OTFTs) were fabricated and characterized using the 9,10-anthracene-based molecules as the semiconductor layer. These findings suggest that functionalization of the 9,10-position of anthracene leads to an effective handle for tuning of the thermal stability, while having little to no effect on the optical properties and the solid-state arrangement.

| S-EPMC6747803 | biostudies-literature

9,10-Dimethyl-9,10-per-oxy-9,10-dihydro-anthracene.

Project description:The structure of the title compound, C(16)H(14)O(2), contains one half-mol-ecule in the asymmetric unit and the mol-ecule is located on a mirror plane. The dihedral angle between the two benzene ring planes is 53.07 (6)°. The crystal structure involves intermolecular C-H⋯O hydrogen bonds.

| S-EPMC2961065 | biostudies-literature

9,10-Dioxo-9,10-di-hydro-anthracene-1,4-diyl di-acetate.

Project description:In the title compound, C18H12O6, the anthra-quinone ring system is nearly planar [maximum deviation = 0.161?(3)?Å] and both acetate groups are located on the same side of the ring plane. A supra-molecular architecture arises in the crystal owing to ?-? stacking between parallel benzene rings of adjacent mol-ecules [centroid-centroid distance = 3.883?(4)?Å] and weak inter-molecular C-H?O hydrogen bonding.

| S-EPMC3648311 | biostudies-literature

1,3-Dihydr-oxy-9,10-dioxo-9,10-di-hydro-anthracene-2-carbaldehyde.

Project description:The title compound, C(15)H(8)O(5), also known as nordamnacanthal, was isolated from the Malaysian Morinda citrifolia L. The 20 non-H atoms are coplanar. The structure is stabilized by intra-molecular O-H?O hydrogen bonds and inter-molecular O-H?O and C-H?O hydrogen bonds, forming bilayers of mol-ecular tapes with alternating stacking directions along the a axis.

| S-EPMC2960756 | biostudies-literature

N,N'-Diphenyl-9,10-dioxo-9,10-di-hydro-anthracene-2,7-disulfonamide.

Project description:The title mol-ecule, C26H18N2O6S2, has an overall Z-shaped conformation, in which the benzene rings are inclined to the anthra-quinone mean plane by 60.60 (9) and 50.66 (13)°. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the bc plane.

| S-EPMC3770431 | biostudies-literature

Poly[[bis-{?2-1,2-bis-[(1H-imidazol-1-yl)meth-yl]benzene}(?4-9,10-dioxo-9,10-dihydro-anthracene-1,4,5,8-tetra-carbox-yl-ato)dicobalt(II)] dihydrate].

Project description:The title complex, {[Co2(C18H4O10)(C14H14N4)2]·2H2O} n was synthesized from CoCl2·6H2O, 9,10-dioxo-9,10-dihydro-anthracene-1,4,5,8-tetra-carb-oxy-lic acid (H4AQTC) and 1,2-bis-[(1H-imidazol-1-yl)meth-yl]benzene (o-bix) in water. The anthraquinone unit is located about a crystallographic center of inversion. Each asymmetric unit therefore contains one Co(II) atom and one o-bix ligand, as well as half an AQTC(4-) ligand and an additional solvent water mol-ecule. The Co(II) ions are tetra-hedrally surrounded by two O atoms from two AQTC(4-) anions and by two N atoms from two o-bix ligands, forming a two-dimensional coordination polymer. The solvent water mol-ecules are connected to the carboxyl-ate groups by O-H?O hydrogen bonds. Additional weak C-H?O hydrogen bonds are observed in the crystal structure.

| S-EPMC3588523 | biostudies-literature

anti-9,10-Di(1-naphth-yl)anthracene pyridine disolvate.

Project description:In the title compound, C(34)H(22)·2C(5)H(5)N, there is a crystallographic inversion center in the middle of the anthracene ring system. The dihedral angle between the mean planes of the anthracene and naphthalene ring systems is 83.96?(4)°. The crystal structure is stabilized by weak inter-molecular C-H?N and C-H?? inter-actions.

| S-EPMC2971459 | biostudies-literature

3,3'-Diethyl-1,1'-[anthracene-9,10-diylbis(oxyethyl-ene)]diimidazolium diiodide.

Project description:In the title centrosymmetric compound, C(28)H(32)N(4)O(2) (2+) 2I(-), the two midazole rings are approximately perpendicular to the central anthracene ring system [dihedral angle = 86.6?(2)°]. The ionic units are linked into a two-dimensional network parallel to (01) by C-H?I hydrogen bonds and ?-? inter-actions involving the anthracene ring system and imidazole rings [centroid-centroid distance = 3.717?(3)?Å].

| S-EPMC2970281 | biostudies-literature

4,4'-(Anthracene-9,10-di-yl)dibenzoic acid dimethyl-formamide disolvate.

Project description:In the title compound, C(28)H(18)O(4)·2C(3)H(7)NO, the dihedral angle between the benzene rings and the anthracene system is 74.05?(12)°. A crystallographic inversion centre is located in the middle of the anthracene unit. The dimethyl-formamide solvent mol-ecules are partially disordered over two positions of approximately equal occupancy [0.529?(6):0.471?(6)]. Inter-molecular O-H?O hydrogen bonds with the major occupancy formamide O atom as acceptor result in the formation of 2:1 solvate-complex aggregates, which are alternately linked to shorter solvate units via weak inter-molecular C-H?O contacts generated from the rotational disorder of the formamide O atom (minor occupancy component). Weak C-H?? inter-actions between the solvent mol-ecules as the donor and the outer anthracene rings support these contacts in the crystal structure for both disorder components.

| S-EPMC2969536 | biostudies-literature

6-[3-(2,4-Dimethyl-anilino)-2-hydroxy-prop-oxy]-1,8-dihydr-oxy-3-methyl-9,10-dihydro-anthracene-9,10-dione.

Project description:In the title compound, C(26)H(25)NO(6), the anthraquinone ring system forms a dihedral angle of 15.5?(1)° with the benzene ring of the dimethyl-aniline group. Intra-molecular O-H?O hydrogen bonding is observed between the carbonyl and two hydroxyl groups. The mol-ecules are linked into a ribbon-like structure along the [100] direction by O-H?N and C-H?O hydrogen bonds. The crystal used was twinned via a 180° rotation about [100]. The ratio of the two twin components is 0.947?(1):0.053?(1).

| S-EPMC2968285 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data