Synthesis of Aminoalkyl-Functionalized 4-Arylquinolines from 2-(3,4-Dihydroisoquinolin-1-yl)anilines via the Friedländer Reaction

Synthesis ◽  
2020 ◽  
Vol 53 (01) ◽  
pp. 146-160
Author(s):  
Yuliya S. Rozhkova ◽  
Tatyana S. Storozheva ◽  
Irina V. Plekhanova ◽  
Alexey A. Gorbunov ◽  
Andrej A. Smolyak ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Easy Access ◽  
New Approach ◽  
Mild Conditions ◽  
Convenient Synthesis

A new approach for the efficient and convenient synthesis of novel aminoalkyl-functionalized 4-arylquinolines via the Friedländer reaction of differently substituted 2-(3,4-dihydroisoquinolin-1-yl)anilines with various α-methylene ketones in acetic acid was developed. The reaction allows easy access to a diversity of 4-arylquinoline derivatives in moderate to excellent yields under mild conditions.

An unusual reaction of a bridged triterpenoid α-diketone with acetic anhydride

1991 ◽  
Vol 56 (12) ◽  
pp. 2917-2935 ◽  
Author(s):  
Eva Klinotová ◽  
Václav Křeček ◽  
Jiří Klinot ◽  
Miloš Buděšínský ◽  
Jaroslav Podlaha ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Nmr Spectroscopy ◽  
Acetic Anhydride ◽  
Spectral Methods ◽  
X Ray Diffraction ◽  
X Ray ◽  
Mild Conditions ◽  
Condensation Products ◽  
Unsaturated Lactones ◽  
C Nmr

3β-Acetoxy-21,22-dioxo-18α,19βH-ursan-28,20β-olide (IIIa) reacts with acetic anhydride in pyridine under very mild conditions affording β-lactone IVa and γ-lactones Va and VIIa as condensation products. On reaction with pyridine, lactones Va and VIIa undergo elimination of acetic acid to give unsaturated lactones VIIIa and IXa, respectively. Similarly, the condensation of 20β,28-epoxy-21,22-dioxo-18α,19βH-ursan-3β-yl acetate (IIIb) with acetic anhydride leads to β-lactone IVb and γ-lactone Vb; the latter on heating with pyridine affords unsaturated lactone VIIIb and 21-methylene-22-ketone Xb. The structure of the obtained compounds was derived using spectral methods, particularly 1H and 13C NMR spectroscopy; structure of lactone IVa was confirmed by X-ray diffraction.

A new approach to arylhydrazides via the reaction of the Mitsunobu reagent with arynes: further application to access diverse nitrogen-containing heterocycles in one pot

2017 ◽  
Vol 4 (8) ◽  
pp. 1636-1639 ◽  
Author(s):  
Bin Cheng ◽  
Bian Bao ◽  
Yanhe Chen ◽  
Ning Wang ◽  
Yun Li ◽  
...  
Keyword(s):  
One Pot ◽  
New Approach ◽  
Mild Conditions ◽  
Highly Active ◽  
Active Intermediates

A new route to arylhydrazides involving the reaction of two highly active intermediates, the 1,3-zwitterion generated in situ from the Mitsunobu reagent and arynes, under mild conditions has been developed.

scholarly journals 2-(2-(4-Methoxyphenyl)-4,9-dimethyl-7-oxo-7H-furo[2,3-f]chromen-3-yl)acetic Acid

Molbank ◽  
10.3390/m1304 ◽  
2021 ◽  
Vol 2021 (4) ◽  
pp. M1304
Author(s):  
Boris V. Lichitsky ◽  
Andrey N. Komogortsev ◽  
Valeriya G. Melekhina
Keyword(s):  
Acetic Acid ◽  
High Resolution Mass Spectrometry ◽  
13C Nmr Spectroscopy ◽  
Acid Moiety ◽  
Acidic Media ◽  
New Approach ◽  
Multicomponent Condensation ◽  
Reaction Proceeds ◽  
Initial Interaction ◽  
First Time

For the first time, we describe a new approach towards the synthesis of previously unknown 2-(2-(4-methoxyphenyl)-4,9-dimethyl-7-oxo-7H-furo[2,3-f]chromen-3-yl)acetic acid. The presented method is based on the multicomponent condensation of 5-hydroxy-4,7-dimethyl-2H-chromen-2-one, 4-methoxyphenylglyoxal and Meldrum’s acid. It was shown that the studied reaction proceeds in two steps including the initial interaction of starting materials in MeCN and the final formation of furylacetic acid moiety in acidic media. The structures of the obtained compound were established by 1H, 13C-NMR spectroscopy and high-resolution mass spectrometry.

Palladium-Catalyzed Desulfurative Hiyama Coupling of Thioureas to Achieve Amides via Selective C–N Bond Cleavage

Synthesis ◽  
2021 ◽  
Author(s):  
Zhuo Zeng ◽  
Zhanyu He ◽  
Chu Yan ◽  
Mei Zhang ◽  
Majeed Irfan ◽  
...  
Keyword(s):  
Good Yield ◽  
Bond Cleavage ◽  
New Approach ◽  
Mild Conditions ◽  
Palladium Catalyzed

AbstractPalladium-catalyzed Hiyama coupling of active thioureas via selective C–N bond cleavage is reported. Notably, the new approach employed active thioureas as coupling partners in the presence of arylsilanes to give amides in good yield. Further, this strategy, which utilized CuF2 as a key oxidant and activator, afforded various amide products under mild conditions and an easy to handle procedure without extra base.

Convenient Synthesis of Fluorescent Chromeno[4,3-d]pyrimidines from Electron-Deficient 3-Vinylchromones

Synthesis ◽  
2019 ◽  
Vol 52 (01) ◽  
pp. 40-50 ◽  
Author(s):  
Nikita M. Chernov ◽  
Roman V. Shutov ◽  
Anastasia E. Potapova ◽  
Igor P. Yakovlev
Keyword(s):  
Stokes Shift ◽  
Mild Conditions ◽  
Convenient Synthesis ◽  
Acid Fragment ◽  
Wide Range ◽  
Powerful Approach ◽  
Reaction Proceeds ◽  
Electron Withdrawing Group ◽  
Blue Range ◽  
Acetic Acids

We report an easy and powerful approach to the synthesis of novel chromeno[4,3-d]pyrimidine-5-acetic acids through ANRORC reaction of electron-deficient 3-vinylchromones and 1,3-N,N-binucleophiles. The reaction proceeds under mild conditions (EtOH, rt) and is applicable to a wide range of substrates. The described compounds show fluorescence in the violet-blue range (390–460 nm) with Stokes shift of 40–80 nm and moderate quantum yield (0.15–0.20). As the electron-withdrawing group is conserved in the form of an acetic acid fragment, these compounds may readily be functionalized or conjugated to a required substrate for (bio)analytical purposes.

scholarly journals Highly efficient epoxidation of vegetable oils catalyzed by a manganese complex with hydrogen peroxide and acetic acid

2019 ◽  
Vol 21 (9) ◽  
pp. 2436-2447 ◽  
Author(s):  
Jianming Chen ◽  
Marc de Liedekerke Beaufort ◽  
Lucas Gyurik ◽  
Joren Dorresteijn ◽  
Matthias Otte ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
Acetic Acid ◽  
Vegetable Oils ◽  
Manganese Complex ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Catalytic Epoxidation

A highly efficient catalytic epoxidation of vegetable oils under mild conditions was developed, using a homogeneous Mn catalyst and H2O2 as oxidant.

scholarly journals Convenient Synthesis of Functionalized Cyclopropa[c]coumarin-1a-carboxylates

Molecules ◽  
2018 ◽  
Vol 24 (1) ◽  
pp. 57 ◽  
Author(s):  
Olga Ivanova ◽  
Vladimir Andronov ◽  
Irina Levina ◽  
Alexey Chagarovskiy ◽  
Leonid Voskressensky ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Aromatic Ring ◽  
Hydroxy Group ◽  
Fine Chemicals ◽  
Simple Method ◽  
Convenient Synthesis ◽  
Donor Acceptor

A simple method has been developed for the synthesis of cyclopropa[c]coumarins, which belong to the donor-acceptor cyclopropane family and, therefore, are promising substrates for the preparation of chromene-based fine chemicals. The method, based on the acetic acid-induced intramolecular transesterification of 2-arylcyclopropane-1,1-dicarboxylates, was found to be efficient for substrates containing hydroxy group directly attached to the aromatic ring.

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