Browse
Submit Data
Databases
API
Help

Dataset Information

26 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P® activation of 3-arylpropiolic acids.

ABSTRACT: In situ activation of 3-arylpropiolic acids with T3P® (n-propylphosphonic acid anhydride) initiates a domino reaction furnishing 4-arylnaphtho[2,3-c]furan-1,3-diones in excellent yields. Upon employing these anhydrides as reactive intermediates blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones are formed by consecutive pseudo three-component syntheses in a one-pot fashion. The Stokes shifts correlate excellently with the Hammett-Taft ?R parameter indicating an extended degree of resonance stabilization in the vibrationally relaxed excited singlet state.

SUBMITTER: Denißen M

PROVIDER: S-EPMC5687056 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P® activation of 3-arylpropiolic acids.

Denißen Melanie M Kraus Alexander A Reiss Guido J GJ Müller Thomas J J TJJ

Beilstein journal of organic chemistry 20171103

In situ activation of 3-arylpropiolic acids with T3P® (n-propylphosphonic acid anhydride) initiates a domino reaction furnishing 4-arylnaphtho[2,3-c]furan-1,3-diones in excellent yields. Upon employing these anhydrides as reactive intermediates blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones are formed by consecutive pseudo three-component syntheses in a one-pot fashion. The Stokes shifts correlate excellently with the Hammett-Taft σ ...[more]

PMID: 29181114

Similar Datasets

N,N'-Di-Boc-2H-Isoindole-2-carboxamidine-First Guanidine-Substituted Isoindole.

Project description:Synthesis of N,N'-Di-Boc-2H-isoindole-2-carboxamidine, the first representative of isoindoles containing guanidine functionality, was carried out. The cycloaddition reactivity of this new Diels-Alder heterodiene was studied and the title compound was employed as a cycloaddition delivery reagent for guanidine functionality. Higher reactivity was found in comparison with the corresponding pyrrole derivative. Substitution with fluorine or guanidine functionality does not change the reactivities of isoindoles, and these findings are in good accord with computational results.

| S-EPMC9781607 | biostudies-literature

Syntheses of 1-Aryl-5-nitro-1H-indazoles and a General One-Pot Route to 1-Aryl-1H-indazoles.

Project description:An efficient route to substituted 1-aryl-1H-indazoles has been developed and optimized. The method involved the preparation of arylhydrazones from acetophenone or benzaldehyde substituted by fluorine at C2 and nitro at C5, followed by deprotonation and nucleophilic aromatic substitution (SNAr) ring closure in 45-90%. Modification of this procedure to a one-pot domino process was successful in the acetophenone series (73-96%), while the benzaldehyde series (63-73%) required a step-wise addition of reagents. A general one-pot protocol for 1-aryl-1H-indazole formation without the limiting substitution patterns required for the SNAr cyclization has also been achieved in 62-78% yields. A selection of 1-aryl-1H-indazoles was prepared in high yield by a procedure that requires only a single laboratory operation.

| S-EPMC6017161 | biostudies-literature

One-Pot Synthesis of Bright Blue Luminescent N-Doped GQDs: Optical Properties and Cell Imaging.

Project description:High fluorescent graphene quantum dots (GQDs) are promising in bioimaging and optoelectronics. In this paper, bright blue fluorescent N-doped GQDs were synthesized using a ultrasonic-assisted hydrothermal method. The morphology, structure, surface chemistry, optical properties, and stability subject to photo-bleaching, temperature, pH and preservation period for the N-GQDs were investigated in detail using various microscopy and spectroscopy techniques. The results showed that the N-GQDs possessed an average size of 2.65 nm, 3.57% N doping, and up to 54% quantum yield (QY). The photoluminescence (PL) spectra of the N-GQDs are excitation dependent when excited in the range of 300-370 nm and excitation independent in the range of 380-500 nm for the core and surface states emission. The N-GQDs showed excellent photo-bleaching resistance and superior photo-stability. At room temperature and in the pH range of 3-8, the fluorescence of the N-GQDs was almost invariable. The N-GQDs can be stably preserved for at least 40 days. The average decay lifetime of the N-GQDs was 2.653 ns, and the radiative and nonradiative decay rate constants were calculated to be 2.04 × 108 s-1 and 1.73 × 108 s-1, respectively. The PL mechanism was qualitatively explained. The N-GQDs was used for cell imaging, and it showed good results, implying great potential applications for bioimaging or biomarking.

| S-EPMC8623353 | biostudies-literature

One-pot synthesis of polycyclic isoindolines using isoindole umpolung.

Project description:Using an isoindole umpolung strategy, a one-pot synthesis of polycyclic isoindolines was accomplished. In this reaction, the in situ-generated nucleophilic isoindoles were converted to electrophilic isoindoliums via protonation, which underwent a Pictet-Spengler-type cyclization to afford a variety of polycyclic isoindolines in good yields.

| S-EPMC9632635 | biostudies-literature

2-(2,3-Dimethyl-phen-yl)-1H-isoindole-1,3(2H)-dione.

Project description:In the title compound, C(16)H(13)NO(2), the 2,3-dimethyl-phenyl group and the 1H-isoindole-1,3(2H)-dione group are essentially planar, with r.m.s. deviations of 0.006 and 0.013 Å, respectively, and are oriented at an angle of 78.19 (3)° with respect to each other. In the crystal, weak C-H⋯O inter-actions link the mol-ecules, forming a zigzag chain parallel to the b axis. Futhermore, C-H⋯π inter-actions are present between the C-H group of isoindole and the 2,3-dimethyl-phenyl benzene ring. The H atoms of the ortho-methyl group are statistically disordered over two positions. Such disorder might be related to the antagonism between intra-molecular steric repulsions and inter-molecular C-H⋯O inter-actions.

| S-EPMC3007846 | biostudies-literature

2-(2-Meth-oxy-phen-yl)-1H-isoindole-1,3(2H)-dione.

Project description:In the title compound, C(15)H(11)NO(3), the dihedral angle between the meth-oxy-benzene and isoindole ring systems is 70.21?(3)°. The meth-oxy C atom is close to being coplanar with its attached ring [deviation = 0.133?(2)?Å] and is oriented away from the isoindole moiety. In the crystal, inversion dimers linked by pairs of C-H?O hydrogen bonds generate R(2) (2)(10) loops. Further C-H?O inter-actions lead to (010) infinite sheets and weak aromatic ?-? stacking [centroid-centroid separations = 3.6990?(10) and 3.7217?(10)?Å] is also observed.

| S-EPMC3415027 | biostudies-literature

One-pot syntheses of immunostimulatory glycolipids.

Project description:Glycolipids containing alpha-linked galactosyl and glucosyl moieties have been shown to possess unique immunostimulatory activity creating a need for access to diverse and anomerically pure sources of these compounds for immunological studies. To meet this demand, glycosyl iodides were enlisted in the synthesis of these biologically relevant glycoconjugates. In the first-generation protocol, per-O-benzyl galactosyl iodide was efficiently coupled with activated sphingosine acceptors, but fully functionalized ceramides were found to be unreactive. To overcome this obstacle, per-O-trimethylsilyl glycosyl iodides were investigated and shown to undergo highly efficient coupling with ceramide and glycerol ester acceptors. Contrary to what has been observed with other donors, we detected little difference between the reactivity of glucosyl and galactosyl iodides. The trimethylsilyl protecting groups play a dual role in activating the donor toward nucleophilic attack while at the same time providing transient protection: the silyl groups are readily removed upon methanolysis. All reactions proceeded with complete acceptor regioselectivity, eliminating the need for additional protecting group manipulations, and the desired alpha-anomers were formed exclusively. This three-step, one-pot synthetic platform provides rapid access to an important class of immunostimulatory molecules including the first reported synthesis of the glucosyl analogue of the bacterial antigen BbGL-II.

| S-EPMC2912955 | biostudies-literature

One-pot phosphine-catalyzed syntheses of quinolines.

Project description:In this study we developed an efficient one-pot procedure for the preparation of 3-substituted and 3,4-disubstituted quinolines from stable starting materials (activated acetylenes reacting with o-tosylamidobenzaldehydes and o-tosylamidophenones, respectively) under mild conditions. The reaction appears to operate under a general base catalysis mechanism, instigated by the β-phosphonium enoate α-vinyl anion generated in situ through nucleophilic addition of PPh(3) to the activated alkyne. Michael addition of the deprotonated tosylamides to the activated alkynes and subsequent rapid aldol cyclization led to the formation of labile N-tosyldihydroquinoline intermediates. Driven by aromatization, detosylation of the dihydroquinoline intermediates occurred readily in the presence of dilute aqueous HCl to give the final quinoline products.

| S-EPMC3459651 | biostudies-literature

2-{[(E)-2-Hy-droxy-benzyl-idene]amino}-1H-isoindole-1,3(2H)-dione.

Project description:In the title compound, C(15)H(10)N(2)O(3), the isoindoline ring system is almost planar [maximum deviation = 0.020?(2)?Å] and makes a dihedral angle of 1.57?(7)° with the benzene ring. Intra-molecular O-H?N and C-H?O hydrogen bonds are observed.

| S-EPMC3009371 | biostudies-literature

Synthesis of sulfur-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones: blue light promoted radical cyclization process.

Project description:The selective and controllable construction of spio-tricyclic skeletons through visible light promoted radical cyclization still remains challenging. Herein, a general and convenient protocol for the blue light-promoted radical-mediated cascade spiro-cyclization/Michael addition of N-arylpropiolamides with thiophenols under metal-free conditions was developed. In this protocol, commercially available hydrochloric acid was employed as the cheap promoter and air as the sustainable oxidant. In addition, many functional groups tolerate the reaction conditions and produce a series of sulfur-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones.

| S-EPMC10184271 | biostudies-literature