Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Titanocene(III) chloride-mediated reductions of oxazines, hydroxamic acids, and N-hydroxy carbamates.

ABSTRACT: Titanocene(III) chloride (Cp(2)TiCl), generated in situ, reduces N-O bonds of various substrates in good to excellent yields (72-95%). Reactions may be performed with stoichiometric Cp(2)TiCl or with catalytic Cp(2)TiCl.

SUBMITTER: Cesario C

PROVIDER: S-EPMC2725442 | biostudies-literature | 2009 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Titanocene(III) chloride-mediated reductions of oxazines, hydroxamic acids, and N-hydroxy carbamates.

Cesario Cara C Tardibono Lawrence P LP Miller Marvin J MJ

The Journal of organic chemistry 20090101 1

Titanocene(III) chloride (Cp(2)TiCl), generated in situ, reduces N-O bonds of various substrates in good to excellent yields (72-95%). Reactions may be performed with stoichiometric Cp(2)TiCl or with catalytic Cp(2)TiCl. ...[more]

PMID: 19053586

Similar Datasets

N-Methylimidazole-catalyzed synthesis of carbamates from hydroxamic acids via the Lossen rearrangement.

Project description:An efficient, one-pot, N-methylimidazole (NMI) accelerated synthesis of aromatic and aliphatic carbamates via the Lossen rearrangement is reported. NMI is a catalyst for the conversion of isocyanate intermediates to the carbamates. Moreover, the utility of arylsulfonyl chloride in combination with NMI minimizes the formation of often-observed hydroxamate-isocyanate dimers during the sequence. Under the present conditions, lowering of temperatures is also possible, enabling a mild protocol.

| S-EPMC3563000 | biostudies-literature

Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents.

Project description:[Bis(trifluoroacetoxy)iodo]benzene (BTI) and (diacetoxyiodo)benzene (DIB) efficiently promote the formation of acylnitroso species from hydroxamic acids in the presence of various dienes to give the corresponding hetero-Diels-Alder (HDA) adducts in moderate to high yields. The present method could be applied to the HDA reactions of acylnitroso species with o-benzoquinones generated by the oxidative dearomatization of guaiacols.

| S-EPMC5852453 | biostudies-literature

Titanocene(III)-Catalyzed Precision Deuteration of Epoxides.

Project description:We describe a titanocene(III)-catalyzed deuterosilylation of epoxides that provides β-deuterated anti-Markovnikov alcohols with excellent D-incorporation, in high yield, and often excellent diastereoselectivity after desilylation. The key to the success of the reaction is a novel activation method of Cp2 TiCl2 and (tBuC5 H4 )2 TiCl2 with BnMgBr and PhSiD3 to provide [(RC5 H4 )2 Ti(III)D] without isotope scrambling. It was developed after discovering an off-cycle scrambling with the previously described method. Our precision deuteration can be applied to the synthesis of drug precursors and highlights the power of combining radical chemistry with organometallic catalysis.

| S-EPMC9305931 | biostudies-literature

Facile Access to Fe(III)-Complexing Cyclic Hydroxamic Acids in a Three-Component Format.

Project description:Cyclic hydroxamic acids can be viewed as effective binders of soluble iron and can therefore be useful moieties for employing in compounds to treat iron overload disease. Alternatively, they are analogs of bacterial siderophores (iron-scavenging metabolites) and can find utility in designing antibiotic constructs for targeted delivery. An earlier described three-component variant of the Castagnoli-Cushman reaction of homophthalic acid (via in situ cyclodehydration to the respective anhydride) was extended to involve hydroxylamine in lieu of the amine component of the reaction. Using hydroxylamine acetate and O-benzylhydroxylamine was key to the success of this transformation due to greater solubility of the reagents in refluxing toluene (compared to hydrochloride salt). The developed protocol was found suitable for multigram-scale syntheses of N-hydroxy- and N-(benzyloxy)tetrahydroisoquinolonic acids. The cyclic hydroxamic acids synthesized in the newly developed format have been tested and shown to be efficient ligands for Fe3+, which makes them suitable candidates for the above-mentioned applications.

| S-EPMC6429155 | biostudies-literature

Titanocene(III)-catalyzed formation of indolines and azaindolines.

Project description:Reductive cyclization of epoxides tethered to substituted anilines and aminopyridines in the presence of 3 mol % of titanocene dichloride and stoichiometric manganese metal promotes a radical annulation to form 3,3-disubstituted indolines and azaindolines.

| S-EPMC5467310 | biostudies-literature

N-amidation by copper-mediated cross-coupling of organostannanes or boronic acids with o-acetyl hydroxamic acids.

Project description:A general nonoxidative N-amidation of organostannanes and boronic acids has been developed. Under nonbasic conditions a wide variety of aryl, alkenyl, and heteroaryl organostannanes and boronic acids couple efficiently with O-acetyl hydroxamic acids in the presence of Cu(I) sources.

| S-EPMC2664512 | biostudies-literature

(R)-(-)-3-Hydroxy-quinuclidinium chloride.

Project description:The quinuclidinium cation of the title compound, C(7)H(14)NO(+)·Cl(-), shows a twist along the C-N pseudo-threefold axis, with N-C-C-C torsion angles of -16.0 (1), -16.9 (1) and -15.6 (1)°. The crystal structure is stabilized by N-H⋯Cl and O-H⋯Cl hydrogen bonds, forming infinite chains along the a and b axes.

| S-EPMC2961231 | biostudies-literature

2-(Hydroxy-meth-yl)pyridinium chloride.

Project description:In the title molecular salt, C(6)H(8)NO(+)·Cl(-), the packing is consolidated by N-H⋯Cl and O-H⋯Cl hydrogen bonds, resulting in the formation of [010] chains of alternating cations and anions.

| S-EPMC2959576 | biostudies-literature

N-Hydroxy-N-methyl-ammonium chloride.

Project description:In the crystal structure of the title compound, CH(6)NO(+)·Cl(-), the cations and anions are linked by N-H⋯Cl and O-H⋯Cl hydrogen bonds into an undulating layer motif [Schläfli symbol: 4(8).6(8).8(2)]. All non-H atoms lie on a mirror plane.

| S-EPMC2961632 | biostudies-literature

4-Hydroxy-ethyl-4-methyl-morpholinium chloride.

Project description:In the title compound, C(7)H(16)NO(2) (+)·Cl(-), the asymmetric unit consists of two cation-anion pairs, in which the ion pairs are inter-connected by weak C-H?Cl hydrogen bonds. Each cation forms a network of weak C-H?Cl hydrogen bonds to surrounding chloride ions. The morpholine ring is in a chair conformation. The crystal structure is consolidated by O-H?Cl, C-H?Cl and C-H?O inter-molecular hydrogen bonding.

| S-EPMC2959307 | 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