Browse
Submit Data
Databases
API
Help

Dataset Information

18 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Facile Access to Substituted 1,4-Diaza-2,3-Diborinines.

ABSTRACT: Several bis(dimethylamino)-substituted 1,4-diaza-2,3-diborinines (DADBs) were synthesized with variable substituents at the backbone nitrogen atoms. By reaction with HCl or BX₃ (X=Br, I), these species were successfully converted into their synthetically more useful halide congeners. The high versatility of the generated B-X bonds in further functionalization reactions at the boron centers was demonstrated by means of salt elimination (MeLi) and commutation (NMe₂ DADBs) reactions, thus making the DADB system a general structural motif in diborane(4) chemistry. A total of 18 DADB derivatives were characterized in the solid state by X-ray diffraction, revealing a strong dependence of the heterocyclic bonding parameters from the exocyclic substitution pattern at boron. According to our experiments towards the realization of a Dipp-substituted, sterically encumbered DADB, the mechanism of DADB formation proceeds via a transient four-membered azadiboretidine intermediate that subsequently undergoes ring expansion to afford the six-membered DADB heterocycle.

SUBMITTER: Thiess T

PROVIDER: S-EPMC7078994 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines.

Project description:It was found that 4-hydroxy-2-butenoic ester (11) could not react with 3,4-dihydro-isoquinoline (4a). Individual addition reactions of γ-mercapto-α,β-unsaturated esters (18) and -unsaturated amide (19) with 3,4-dihydroisoquinolines (4) were carried out under appropriate conditions to provide the corresponding thiazolo[2,3-α]isoquinoline derivatives with good yields (up to 87%) and significant diastereomeric selectivity. The mechanism of the crucial reaction was discussed.

| S-EPMC8537374 | biostudies-literature

C-Methyl-calix[4]resorcinarene-1,4-bis-(pyridin-3-yl)-2,3-diaza-1,3-butadiene (1/2).

Project description:In the title compound, 2C(12)H(10)N(4)·C(32)H(32)O(8), the calixarene adopts a rctt conformation with dihedral angles of 138.40 (1) and 9.10 (1)° between the opposite rings. The dihedral angles between the rings of the pyridine derivative are 8.80 (1) and 9.20 (1)°. In the crystal, adjacent C-methylcalix[4]resorcinarene molecules are connected into columns parallel to [010] by O-H⋯O hydrogen bonds. O-H⋯N hydrogen bonds between the axial phenoxyl groups and bipyridine molecules link the columns into sheets parallel to (011), which are connected by O-H⋯N hydrogen bonds. Further O-H⋯N hydrogen bonds link the bipyridine and C-methylcalix[4]resorcinarene molecules, giving rise to a three-dimensional network.

| S-EPMC3274953 | biostudies-literature

1,4-Bis(4-bromo-2,6-diisopropyl-phen-yl)-1,4-diaza-buta-1,3-diene.

Project description:The molecule of the title compound, C(26)H(34)Br(2)N(2), lies on a crystallographic inversion center and hence the two imine groups are s-trans. The dihedral angle between the central 1,4-diaza-buta-1,3-diene unit and the attached substituted phenyl ring is 88.4?(7)°. The structure features a C-H?N close contact. The crystal selected for this study proved to be a non-merohedral twin with a minor component of 21.8?(3)%.

| S-EPMC2980129 | biostudies-literature

Intramolecular radical cyclization approach to access highly substituted indolines and 2,3-dihydrobenzofurans under visible-light.

Project description:The combination of visible-light and tris(trimethylsilyl)silane promoting intramolecular reductive cyclization protocol for the synthesis of functionalized indolines and 2,3-dihydrobenzofurans has been developed. The transformations occur in the absence of transition metal and additional photocatalyst. In addition, quantum yield (Φ) was determined and electron paramagnetic resonance spectroscopy was performed to better understand the reaction pathway.

| S-EPMC9079632 | biostudies-literature

Benzene-1,3-diol-1,4-diaza-bicyclo-[2.2.2]octane (1/1).

Project description:There are two independent but virtually identical mol-ecules of each component in the asymmetric unit of the title 1:1 adduct, C(6)H(12)N(2)·C(6)H(6)O(2). In the crystal, the constituents are connected into a supra-molecular chain along the b axis by O-H?N hydrogen bonds. Weak C-H?O bonds cross-link the chains.

| S-EPMC3007329 | biostudies-literature

1,3,5-Tris(pyridin-3-yl)-2,4-diaza-penta-1,4-diene.

Project description:In the solid state, the structure of the title compound, C(18)H(15)N(5), is stabilized by weak C-H?N interactions. Mol-ecules are arranged in layers parallel to the bc plane forming an inter-esting supra-molecular structure.

| S-EPMC3295514 | biostudies-literature

1,4-Dibromo-butane-2,3-dione.

Project description:The asymmetric unit of the title compound, C(4)H(4)Br(2)O(2), contains one half-mol-ecule, being located about a centre of inversion. In the crystal, there are no significant inter-molecular inter-actions.

| S-EPMC3515323 | biostudies-literature

1,4-Dibromo-naphthalene-2,3-diol.

Project description:In the title compound (r.m.s. deviation for the non-H atoms = 0.020?Å), C(10)H(6)Br(2)O(2), an intra-molecular O-H?O hydrogen bond generates an S(6) ring. In the crystal, the same H atom also forms an inter-molecular O-H?O hydrogen bond, generating a C(2) chain propagating in [100]. The other O-H hydrogen forms a weak O-H?? inter-action, and short Br?Br contacts [3.5972?(9)?Å] also occur.

| S-EPMC3213464 | biostudies-literature

1,4-Dichloro-naphthalene-2,3-diol.

Project description:The achiral planar (maximum deviation 0.014?Å) title compound, C(10)H(6)Cl(2)O(2), crystallizes in the chiral space group P2(1)2(1)2(1) in an arrangement incorporating conventional O-H?O hydrogen bonding leading to a supra-molecular chain.

| S-EPMC2968610 | biostudies-literature

2,3-Dichloro-benzene-1,4-diol.

Project description:The achiral title compound, C(6)H(4)Cl(2)O(2), crystallizes with O-H⋯O hydrogen bonding linking mol-ecules into layers. Between layers there are chains of Cl⋯Cl⋯Cl inter-actions with alternating distances of 3.274 (2) and 3.742 (2) Å. Augmenting this arrangement there are also C-H⋯Cl (2.97 and 3.17 Å) and Cl⋯π (shortest distances 3.40 and 3.54 Å) inter-actions.

| S-EPMC2977781 | 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