Double bond terminated Ln3+-doped LiYF4 nanocrystals with strong single band NIR emission: simple click chemistry route to make water dispersible nanocrystals with various functional groups

5(O)n and 6(O)π,n participations by some oxygen containing functional groups in the course of reaction with hypobromous acid have been studied on olefinic models of steroid type (I and II). The ability of these groups to participate has been compared on the basis of their relative reactivity with water (as externally attacking nucleophile) competing with participation. The results of the product analysis show that the ability to react with 5(O)n participation decreases in the order HO > CH3O ≃ CH3OCH2O > CH3CO2 > HCO2 > CH3SO3 ≥ (C2H5O)2PO2 > C6H5CO2 > O2NO ≫ CF3CO2, C2H5OCO2; in the last two functional groups is this ability completely suppressed. The 6(O)π,n participation comes in consideration only for compounds of the type II bearing the groups with the -X=O moiety which are ordered in the following sequence: C2H5OCO2 ≃ CH3CO2 ≥ (C2H5O)2PO2 > HCO2 > C6H5CO2. The remaining functional groups (CF3CO2, O2NO and CH3SO3do not undergo this process. Generally, it is valid that introduction of electron-withdrawing substituents into a participating group impedes or completely suppresses its ability to participate.

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Water-dispersible fluorescent nanodiamonds for biological imaging prepared by thiol-ene click chemistry

Journal of the Taiwan Institute of Chemical Engineers ◽

10.1016/j.jtice.2018.08.035 ◽

2019 ◽

Vol 95 ◽

pp. 481-486 ◽

Cited By ~ 5

Author(s):

Hongye Huang ◽

Meiying Liu ◽

Ruming Jiang ◽

Junyu Chen ◽

Qiang Huang ◽

...

Keyword(s):

Click Chemistry ◽

Biological Imaging ◽

Water Dispersible ◽

Fluorescent Nanodiamonds

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Cu(II)-Catalyzed [3+2] Annulation of Thioamides with AIBN: Facile Access to Highly Functionalized Thiazolidine-4-ones

Synthesis ◽

10.1055/a-1693-7535 ◽

2021 ◽

Author(s):

Pragya Pali ◽

Dhananjay Yadav ◽

Gaurav Shukla ◽

Maya Shankar Singh

Keyword(s):

Double Bond ◽

Functional Groups ◽

Dual Role ◽

Direct Access ◽

One Pot ◽

Simple Method ◽

Two Component ◽

Thiazolidine Ring ◽

Coupling Partner

An efficient and versatile copper-catalyzed unprecedented intermolecular radical [3 + 2] annulation of thioamides with azobisisobutyronitrile (AIBN) is described. This two-component one-pot copper(II)-catalyzed transformation has been achieved via cascade formation of C-S/C−N bonds through the cyclization of in situ generated N,S-acetal intermediate from β-ketothioamide. This operationally simple method allows direct access to synthetically demanding thiazolidin-4-ones in good to excellent yields containing diverse functional groups of different electronic and steric nature. Remarkably, the readily available reaction partners, avoidance of expensive/toxic reagents and the gram scale synthesis are additional attributes to this strategy. AIBN here plays a dual role as radical initiator and unusual source of two carbon coupling partner. Notably, the products possess Z-stereochemistry with regard to the exocyclic C=C double bond at the 2-position of the thiazolidine ring.

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Naphthalimide Dyes with Orthogonal Functional Groups for “Click” Chemistry: Attachment to Solid Supports and Applications in Drug Allergy Diagnosis

ChemPlusChem ◽

10.1002/cplu.202000118 ◽

2020 ◽

Vol 85 (4) ◽

pp. 689-693

Author(s):

Antonio J. Ruiz‐Sanchez ◽

Daniel Collado ◽

Cristobalina Mayorga ◽

Maria J. Torres ◽

Ezequiel Perez‐Inestrosa

Keyword(s):

Click Chemistry ◽

Functional Groups ◽

Drug Allergy ◽

Allergy Diagnosis ◽

Solid Supports

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Rational design of water-dispersible and biocompatible nanoprobes with H2S-triggered NIR emission for cancer cell imaging

Journal of Materials Chemistry B ◽

10.1039/d0tb00173b ◽

2020 ◽

Vol 8 (28) ◽

pp. 6013-6016

Author(s):

Hengyan Liu ◽

Ge Xu ◽

Tianli Zhu ◽

Rongchen Wang ◽

Jiahui Tan ◽

...

Keyword(s):

Cancer Cells ◽

Cancer Cell ◽

Small Molecule ◽

Rational Design ◽

Cell Imaging ◽

Imaging Modality ◽

Aqueous Solubility ◽

Water Dispersible ◽

Nir Emission ◽

Small Molecule Probe

A nanoprobe with good aqueous solubility and biocompatibility by trapping an H2S-activatable small molecule probe in the interior of surface cross-linked micelles was fabricated for imaging of H2S-rich cancer cells in a dual-color imaging modality.

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Click chemistry-based synthesis of water-dispersible hydrophobic magnetic nanoparticles for use in solid phase extraction of non-steroidal anti-inflammatory drugs

Microchimica Acta ◽

10.1007/s00604-015-1638-x ◽

2015 ◽

Vol 182 (15-16) ◽

pp. 2585-2591 ◽

Cited By ~ 14

Author(s):

Zhi-yuan Luo ◽

Zhi-yong Li ◽

Hai-yan Liu ◽

Min-qiong Tang ◽

Zhi-guo Shi

Keyword(s):

Magnetic Nanoparticles ◽

Solid Phase Extraction ◽

Click Chemistry ◽

Solid Phase ◽

Phase Extraction ◽

Water Dispersible ◽

Inflammatory Drugs ◽

Anti Inflammatory

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A biomimetic approach to some specifically functionalized cyclic terpenoids.

Acta Biochimica Polonica ◽

10.18388/abp.2007_3132 ◽

2007 ◽

Vol 54 (4) ◽

pp. 679-693 ◽

Cited By ~ 4

Author(s):

Veaceslav Kulciţki

Keyword(s):

Double Bond ◽

Functional Groups ◽

Ring Closure ◽

Living Systems ◽

Open Chain ◽

Initial Substrate ◽

Alpha Omega ◽

Biomimetic Approach

The paper relates on the current advancements in the synthesis of complex cyclic terpenoids by superacidic induced cyclization of open chain precursors. It is shown that functional groups disposal in the initial substrate strongly influences the reaction outcome. Possible variations of the investigated compound structures include particularly alpha-functionalization and alpha,omega-bifunctionalization. This approach allowed a selective initiation of cyclization sequence from an internal double bond or suspending the ring closure cascade to partially cyclized compounds. The reported synthetic schemes are attempts to mimic the biogenetical processes postulated in the living systems.

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Variability of Rhodium(III)-Catalyzed Reactions of Aromatic Oximes with Alkenes

Synlett ◽

10.1055/s-0040-1707961 ◽

2020 ◽

Vol 31 (11) ◽

pp. 1117-1120 ◽

Cited By ~ 1

Author(s):

Dmitry S. Perekalin ◽

Evgeniya A. Trifonova ◽

Alina A. Komarova ◽

Denis Chusov

Keyword(s):

Double Bond ◽

Functional Groups ◽

Rhodium Catalyst ◽

The Other ◽

Chiral Catalyst ◽

Enantiomeric Ratio ◽

Other Hand ◽

Terminal Alkenes ◽

Catalyzed Reactions ◽

Acetophenone Oxime

Acetophenone oxime reacts with various alkenes in the presence of the rhodium catalyst [Cp*RhCl2]2 (2.5 mol%; Cp* = pentamethylcyclopentadienyl) and 1,1,1,3,3,3-hexafluoropropan-2-ol as an important cosolvent. Styrene, aliphatic terminal alkenes, and strained cyclic alkenes gave the corresponding substituted dihydroisoquinolines in yields of 50–99%. On the other hand, alkenes containing functional groups close to the double bond gave a variety of different products. The reactions of acetophenone oxime with styrene or dec-1-ene in the presence of the chiral catalyst [(C5H2 t Bu2CH2 t Bu)RhI2]2 provided the corresponding dihydroisoquinolines with improved regioselectivity but a low enantiomeric ratio (61:39 in both cases).

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Silver(I)-Catalyzed Deprenylation of Allylsulfonamide Derivatives

Synlett ◽

10.1055/s-0036-1589066 ◽

2017 ◽

Vol 28 (16) ◽

pp. 2143-2146 ◽

Cited By ~ 4

Author(s):

Fuyuhiko Inagaki ◽

Shisen Hira ◽

Chisato Mukai

Keyword(s):

Double Bond ◽

Nitrogen Atom ◽

Functional Groups ◽

Silver Cation ◽

Elimination Reaction

The silver(I)-catalyzed deprenylation of sulfonamide bearing prenyl functional groups on the nitrogen atom has been developed. In this reaction, the prenyl moiety was selectively eliminated without allyl or benzyl cleavage on the nitrogen atom. In addition, geranyl was also applicable for this elimination reaction. Furthermore, sulfonamide possessing two prenyl groups underwent a double deprenylation to form the corresponding deprenylated sulfonamide. Thus, a novel reactivity between the silver cation and double bond was observed.

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