A Base‐ and Metal‐free Protocol for the Synthesis of 2‐Aryl/heteroaryl Thiazolines

Chaudhary, Shweta; Milton, Marilyn Daisy; Garg, Parul

doi:10.1002/slct.201601553

Cited by 9 publications

(4 citation statements)

References 43 publications

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“…Next, the acceptor –CN group of A−D‐A molecule A was transformed into thiazoline ring. The synthesis of 3,7 ‐bis( 4 ‐( 4,5 ‐dihydrothiazol‐ 2 ‐yl)phenyl)‐ 10 ‐ethyl‐ 10H ‐phenothiazine‐ 5 ‐oxide ( 3 h ) was carried out by refluxing 4,4’ ‐(10‐ethyl‐ 5 ‐oxido‐ 10H ‐phenothiazine‐ 3,7 ‐diyl)dibenzonitrile ( A ) with cysteamine hydrochloride ( B ) in the presence of Na 2 CO 3 as base at 110 °C in toluene for 15 h under nitrogen atmosphere (95% yield, Scheme ).…”

Section: Resultssupporting

confidence: 93%

Novel Phenothiazine‐5‐oxide Based Push‐Pull Molecules: Synthesis and Fine‐Tuning of Electronic, Optical and Thermal Properties

et al. 2018

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A series of eight acceptor-donor-acceptor (A-D-A) type small push-pull compounds based on non-planar phenothiazine-5oxide as central donor building block end-capped with different accepting groups were synthesized and characterized. These A-D-A systems were evaluated for their electronic, optical and thermal properties by density functional theory (DFT), UV-Vis, fluorescence, thermo gravimetric analysis (TGA) and differential thermal analysis (DTA) methods. Single crystal X-ray diffraction (XRD) and DFT studies revealed near-planar geome-try for N-aryl substituted over N-alkyl substituted phenothiazine moiety in these A-D-A molecules leading to better orbital overlap and stabilization through intramolecular charge transfer (ICT) transition. The HOMO-LUMO energy gap was observed in the range of 3.70-4.28 eV. Photoluminescence (PL) studies showed triple as well as dual fluorescence with red-shifted spectra. Also, TGA and DTA studies indicated moderate to good thermal stability with decomposition temperature (T d ) in the range of 159-302 8C.

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Section: Resultssupporting

confidence: 93%

Novel Phenothiazine‐5‐oxide Based Push‐Pull Molecules: Synthesis and Fine‐Tuning of Electronic, Optical and Thermal Properties

et al. 2018

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“…The spectroscopic data of N -butyl- N -(4-cyanobenzyl)butan-1-amine ( 38 ) are in accordance with the literature. 68…”

Section: N -Butyl- N -(4-cyanobenzyl)butan-1-...mentioning

confidence: 99%

Selective Csp3–F Bond Functionalization with Lithium Iodide

Wolf¹,

Balaraman²,

Kyriazakos³

et al. 2022

Synthesis

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A highly efficient method for C–F bond functionalization of a broad variety of activated and unactivated aliphatic substrates with inexpensive lithium iodide is presented. Primary, secondary, tertiary, benzylic, propargylic and α-functionalized alkyl fluorides react in chlorinated or aromatic solvents at room temperature or upon heating to give the corresponding iodides, which are isolated in 91–99% yield. The reaction is selective for aliphatic monofluorides and can be coupled with in situ nucleophilic iodide replacements to install carbon–carbon, carbon–nitrogen, and carbon–sulfur bonds with high yields. Alkyl difluorides, trifluorides, even in activated benzylic positions, are inert under the same conditions and aryl fluoride bonds are also tolerated.

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“…Encouraged by our recent findings of synthetic route for 2-aryl/ heteroarylthiazolines under base-and metal-free reaction conditions, [57] we have optimized the reaction conditions for the synthesis of 2-arylbenzothiazoles. The synthetic route for the synthesis of 2-arylbenzothiazoles 3 a-3 k is shown in Table 1.…”

Section: Synthesis and Characterization Of 2-arylbenzothiazolementioning

confidence: 99%

Novel 2‐Arylbenzothiazoles: Selective Chromogenic and Fluorescent Probes for the Detection of Picric Acid

2018

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A series of 2‐arylbenzothiazoles has been designed and synthesized as chromogenic and fluorescent probes for the detection of picric acid (PA) over other nitro analytes. A straightforward condensation of a variety of aryl nitriles with 2‐aminobenzenethiol under metal‐ and base‐free conditions afforded the corresponding products in 26–98% yields. All 2‐arylbenzothiazoles could efficiently sense PA at micromolar levels. The highly sensitive compound 2‐(4‐((2‐methyl‐1H‐imidazol‐1‐yl)methyl)phenyl)benzo[d]thiazole (3c) showed 95% fluorescence quenching on addition of 1.0 eq of PA which can be attributed to hydrogen bonding and ground state charge transfer complex formation with a detection limit of 19.0 μM. The high sensitivity of 3 c for PA detection was also established by test strips experiment. The sensing mechanism was explored by 1H NMR titrations and Job's plot.

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A Base‐ and Metal‐free Protocol for the Synthesis of 2‐Aryl/heteroaryl Thiazolines

Cited by 9 publications

References 43 publications

Novel Phenothiazine‐5‐oxide Based Push‐Pull Molecules: Synthesis and Fine‐Tuning of Electronic, Optical and Thermal Properties

Novel Phenothiazine‐5‐oxide Based Push‐Pull Molecules: Synthesis and Fine‐Tuning of Electronic, Optical and Thermal Properties

Selective Csp3–F Bond Functionalization with Lithium Iodide

Novel 2‐Arylbenzothiazoles: Selective Chromogenic and Fluorescent Probes for the Detection of Picric Acid

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