Browse
Submit Data
Databases
API
Help

Dataset Information

5 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Metal-free, efficient hydrazination of imidazo[1,2-a]pyridine with diethyl azodicarboxylate in neutral media.

ABSTRACT: The first example of metal-free regioselective hydrazination of imidazo[1,2-a]pyridine with diethyl azodicarboxylate is accomplished. This procedure is chemically appealing due to the high degree of functional group tolerance and efficiency in expanding the molecular diversity.

SUBMITTER: Wang Y

PROVIDER: S-EPMC4675458 | biostudies-other | 2015 Mar

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Publications

Metal-free, efficient hydrazination of imidazo[1,2-a]pyridine with diethyl azodicarboxylate in neutral media.

Wang Yuanxiang Y Frett Brendan B McConnell Nick N Li Hong-Yu HY

Organic & biomolecular chemistry 20150301 10

The first example of metal-free regioselective hydrazination of imidazo[1,2-a]pyridine with diethyl azodicarboxylate is accomplished. This procedure is chemically appealing due to the high degree of functional group tolerance and efficiency in expanding the molecular diversity. ...[more]

PMID: 25611884

Similar Datasets

Efficient and "Green" Synthetic Route to Imidazo[1,2-a]pyridine by Cu(II)-Ascorbate-Catalyzed A3-Coupling in Aqueous Micellar Media.

Project description:An efficient and environmentally sustainable method for the synthesis of imidazo[1,2-a]pyridine derivatives by domino A3-coupling reaction catalyzed by Cu(II)-ascorbate was developed in aqueous micellar media in the presence of sodium dodecyl sulfate (SDS). The catalyst, a dynamic combination of Cu(II)/Cu(I), was generated in situ in the reaction mixture by mixing CuSO4 with sodium ascorbate and aided a facile 5-exo-dig cycloisomerization of alkynes with the condensation products of 2-aminopyridines and aldehydes to afford a variety of imidazo[1,2-a]pyridines in good overall yields. A simple experimental setup, water as the "green" medium, and inexpensive catalyst and auxiliary are some of the merits of this protocol.

| S-EPMC6647986 | biostudies-literature

Ethyl 5-methyl-imidazo[1,2-a]pyridine-2-carboxyl-ate.

Project description:The title compound, C(11)H(12)N(2)O(2), was synthesized from the reaction of 6-methyl-pyridin-2-amine and ethyl 3-bromo-2-oxopropionate. In the mol-ecular structure, the six- and five-membered rings are individually almost planar with r.m.s. deviations of 0.003 and 0.002?Å, respectively. The two rings are almost coplanar, the dihedral angle between their planes being 1.4?(3)°. Inter-molecular C-H?O and C-H?N hydrogen bonds are present in the crystal structure.

| S-EPMC3007311 | biostudies-literature

2-(Ethyl-sulfin-yl)imidazo[1,2-a]pyridine-3-sulfonamide.

Project description:The supra-molecular structure of the title compound, C(9)H(11)N(3)O(3)S(2), is defined by two inter-molecular hydrogen bonds. Pairs of N-H?N hydrogen bonds link the mol-ecules into centrosymmetric dimers and N-H?O hydrogen bonds link the dimers into a tubular chain structure running parallel to the a axis.

| S-EPMC3344477 | biostudies-literature

Imidazo[1,2-a]pyridine-based peptidomimetics as inhibitors of Akt.

Project description:We report the design, synthesis, and biological evaluation of imidazopyridine-based peptidomimetics based on the substrate consensus sequence of Akt, an AGC family serine/threonine kinase hyperactivated in over 50% of human tumors. Our ligand-based approach led to the identification of novel substrate mimetic inhibitors of Akt1 featuring an unnatural extended dipeptide surrogate. Compound 11 inhibits Akt isoforms in the sub-micromolar range and exhibits improved proteolytic stability relative to a parent pentapeptide.

| S-EPMC4176526 | biostudies-literature

Gold Catalysed Redox Synthesis of Imidazo[1,2-a]pyridine using Pyridine N-Oxide and Alkynes.

Project description:A mild, catalytic, atom economical synthesis of imidazo[1,2-a]pyridines has been developed: catalytic PicAuCl2 in the presence of an acid produces a range imidazo[1,2-a]pyridines in good yield. This strategy is mild and forseen to be of particular use for the installation of stereogenic centers adjacent to the imidazo[1,2-a]pyridine ring without loss of enantiomeric excess.

| S-EPMC4019451 | biostudies-literature

2-Phenyl-imidazo[1,2-a]pyridine-3-carbaldehyde.

Project description:In the title compound, C(14)H(10)N(2)O, the dihedral angle between the imidazo[1,2-a]pyridine and phenyl rings is 28.61?(4)° The mol-ecules are connected into broad chains parallel to the a axis by weak C-H?O and C-H?N hydrogen bonds. The linking of the ribbons is provided by ?-? stacking inter-actions between neighbouring pyridine rings, with a centroid-centroid distance of 3.7187?(7)?Å.

| S-EPMC2961188 | biostudies-other

Identification of novel imidazo[1,2-a]pyridine inhibitors targeting M. tuberculosis QcrB.

Project description:Mycobacterium tuberculosis is a major human pathogen and the causative agent for the pulmonary disease, tuberculosis (TB). Current treatment programs to combat TB are under threat due to the emergence of multi-drug and extensively-drug resistant TB. Through the use of high throughput whole cell screening of an extensive compound library a number of imidazo[1,2-a]pyridine (IP) compounds were obtained as potent lead molecules active against M. tuberculosis and Mycobacterium bovis BCG. The IP inhibitors (1-4) demonstrated minimum inhibitory concentrations (MICs) in the range of 0.03 to 5 µM against a panel of M. tuberculosis strains. M. bovis BCG spontaneous resistant mutants were generated against IP 1, 3, and 4 at 5× MIC and subsequent whole genome sequencing identified a single nucleotide polymorphism (937)ACC>(937)GCC (T313A) in qcrB, which encodes the b subunit of the electron transport ubiquinol cytochrome C reductase. This mutation also conferred cross-resistance against IP 1, 3 and 4 demonstrating a common target. Gene dosage experiments confirmed M. bovis BCG QcrB as the target where over-expression in M. bovis BCG led to an increase in MIC from 0.5 to >8 µM for IP 3. An acute murine model of TB infection established bacteriostatic activity of the IP series, which await further detailed characterization.

| S-EPMC3534098 | biostudies-literature

A practical and efficient approach to imidazo[1,2-a]pyridine-fused isoquinolines through the post-GBB transformation strategy.

Project description:Diversity-oriented synthesis of the biologically intriguing imidazo[1,2-a]pyridine-fused isoquinoline systems from readily available starting materials was achieved through the Groebke-Blackburn-Bienaymé reaction followed by a gold-catalyzed cyclization strategy. The synthetic approach is characterized by mild reaction conditions and a broad substrate scope, allowing for the rapid construction of structurally complex and diverse heterocycles in moderate to good yields.

| S-EPMC5433183 | biostudies-literature

Ethyl 8-(4-nitro-phen-yl)imidazo[1,2-a]pyridine-7-carboxyl-ate.

Project description:In the title compound, C(16)H(13)N(3)O(4), the imidazo[1,2-a]pyridine and benzene rings make a dihedral angle of 56.21?(2)°. The crystal packing is stabilized by weak ?-? stacking inter-actions [centroid-centroid distances = 3.787?(2)?Å] and C-H?O inter-molecular hydrogen-bonding inter-actions.

| S-EPMC3011613 | biostudies-literature

[N,N'-(1,2-Diphenyl-ethane-1,2-di-yl)bis-(pyridine-2-carboxamidato)]nickel(II) diethyl ether hemisolvate.

Project description:In the title compound, [Ni(C(26)H(20)N(4)O(2))]·0.5C(4)H(10)O, the central metal ion is coordinated by four atoms of the tetra-dentate picolinamide ligand, forming a slightly distorted square-planar configuration, with an average Ni-N(pyridine) distance of 1.94?Å and an average Ni-N(amide) distance of 1.83?Å. The asymmetric unit contains one half-molecule of diethyl ether; this solvent molecule is disordered across a twofold rotation axis..

| S-EPMC2960759 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

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