A Mild Titanium‐Catalyzed Synthesis of Functionalized Amino Coumarins as Fluorescence Labels

Wirtz, Lisa; Kazmaier, Uli

doi:10.1002/ejoc.201101117

Cited by 20 publications

(12 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…2f (0.47 g, 3.11 mmol) reacts with 1 (0.42 g, 2.10 mmol) in THF (method C ), giving a complex mixture of products, where E- 4f (4%), syn - 11f (8%), anti - 12f (2%), 6f (25%), and methyl ( Z )-3-hydroxy-3-(4-nitrophenyl)acrylate ( 13 , 7%) were observed. Yields of these products were appreciated by 1 H and 19 F NMR spectra.…”

Section: Methodsmentioning

confidence: 99%

SF₅-Enolates in Ti(IV)-Mediated Aldol Reactions

et al. 2016

View full text Add to dashboard Cite

The F···Ti bonding in the transition structures determines high trans- and syn-diastereoselectivities for aldol reactions of SF5-acetates with aldehydes in the presence of TiCl4 in the non-nucleophilic solvent CH2Cl2. Such bonding is canceled in nucleophilic solvents where opposite cis-stereochemistry is observed. The potential of thus obtained stereoisomeric SF5-aryl acrylates as dipolarophiles in the preparation of SF5-containing heterocycles is demonstrated.

show abstract

Section: Methodsmentioning

confidence: 99%

SF₅-Enolates in Ti(IV)-Mediated Aldol Reactions

et al. 2016

View full text Add to dashboard Cite

show abstract

“…Heteropolycycles based on julolidine are extremely valuable and are applied in industry and also in biological systems, such as photoconductive materials,25 nonlinear optical materials,26,27 highly fluorescent molecular rotors,28,29 chemiluminescent dyes,30,31 chromogenic substrates in analytical redox reactions,32 potential antidepressants and tranquilizers 33. Considering the importance of the julolidine structural motif, the synthesis of new structurally diverse julolidine derivatives that can benefit from its properties represents a challenge27,34,35 and, recently, the first synthesis of a julolidine‐fused heteroaromatic with coumarin has been reported for application as a fluorescent label 36…”

Section: Introductionmentioning

confidence: 99%

Photoinduced Release of Neurotransmitter Amino Acids from Coumarin‐Fused Julolidine Ester Cages

Piloto¹,

Hungerford²,

Costa³

et al. 2013

Eur J Org Chem

View full text Add to dashboard Cite

The photoinduced release of several neurotransmitter amino acids (glycine, alanine, glutamic acid, β‐alanine and γ‐aminobutyric acid) was accomplished from ester cages based on a new photoremovable protecting group consisting of a coumarin built on the julolidine nucleus, namely a (11‐oxo‐2,3,5,6,7,11‐hexahydro‐1H‐pyrano[2,3‐f]pyrido[3,2,1‐ij]quinolin‐9‐yl)methyl group. Photolysis and steady‐state sensitization studies revealed that release of the active molecule occurred in short irradiation times at long wavelengths, with a very promising performance at 419 nm. Given the interest in the development of novel protecting groups that are cleavable with UV A or even visible radiation, it was found that a structural modification in the coumarin ring by assembly of a fused julolidine leads to a promising photolabile protecting group for organic synthesis and also for bioapplications.

show abstract

“…Adding a halogen atom has been already listed in the literature to cause a bathochromic shift of 30 nm on similar structures. [16,17] Hence, UVvisible absorption and fluorescence emission spectra for FFN122 show a maximum absorption wavelength of 388 nm and a maximum emission wavelength of 471 nm (Figure 2D). This compound therefore has an absorption maximum closer to the wavelength excitation laser available in laboratories in visible range (laser 405 nm).…”

Section: Spectroscopic Properties Of Screened Ffnsmentioning

confidence: 97%

From FFN Dual Probe Screening to ITO Microdevice for Exocytosis Monitoring: Electrochemical and Fluorescence Requirements**

et al. 2022

View full text Add to dashboard Cite

In this work, four different new fluorescent false neurotransmitters (FFN) probes were synthesized to contribute to the rationale of the FFN design. Their electroactive and spectroscopic properties were investigated. Hence, the optimal excitation and emission wavelengths (from 344 to 393 nm and 423 to 474 nm, respectively) make these probes adapted to fluorescence microscopy. Moreover, their electroactivity were demonstrated to occur at relatively low oxidation potentials for three of them (FFN132, FFN145 and FFN122: 0.26, 0.25 and 0.30 V vs. Ag/AgCl, respectively) and at 0.74 V vs. Ag/AgCl for FFN21 on carbon fiber electrodes. However, epifluorescence observations evidenced that the new designed FFN with the best spectroscopic and electrochemical properties (FFN122) did unfortunately not accumulate into secretory vesicles of model BON N13 cells. It thus confirms that FFN42 is currently the best “bioelectrofluorescent” compromise. This is why total internal fluorescence reflection microscopy measurements were then studied with the model FFN42 and BON N13 cells. Beyond the choice of the appropriate FFN, other analytical requirements are needed. As a consequence, the features of the transparent and conducting indium tin oxide (ITO) microdevice for coupled amperometry‐fluorescent measurements were investigated and optimized in terms of effects on the electrochemical performances and reusability. These results pave the way for future coupled investigations of exocytosis with the FFN‐ITO device association.

show abstract

A Mild Titanium‐Catalyzed Synthesis of Functionalized Amino Coumarins as Fluorescence Labels

Cited by 20 publications

References 29 publications

SF₅-Enolates in Ti(IV)-Mediated Aldol Reactions

SF₅-Enolates in Ti(IV)-Mediated Aldol Reactions

Photoinduced Release of Neurotransmitter Amino Acids from Coumarin‐Fused Julolidine Ester Cages

From FFN Dual Probe Screening to ITO Microdevice for Exocytosis Monitoring: Electrochemical and Fluorescence Requirements**

Contact Info

Product

Resources

About

A Mild Titanium‐Catalyzed Synthesis of Functionalized Amino Coumarins as Fluorescence Labels

Cited by 20 publications

References 29 publications

SF5-Enolates in Ti(IV)-Mediated Aldol Reactions

SF5-Enolates in Ti(IV)-Mediated Aldol Reactions

Photoinduced Release of Neurotransmitter Amino Acids from Coumarin‐Fused Julolidine Ester Cages

From FFN Dual Probe Screening to ITO Microdevice for Exocytosis Monitoring: Electrochemical and Fluorescence Requirements**

Contact Info

Product

Resources

About

SF₅-Enolates in Ti(IV)-Mediated Aldol Reactions

SF₅-Enolates in Ti(IV)-Mediated Aldol Reactions