Physicochemical properties of a urea/zinc chloride eutectic mixture and its improved effect on the fast and high yield synthesis of indeno[2,1-c]quinolines

2020 ◽  
Vol 44 (19) ◽  
pp. 7987-7997
Author(s):  
Diana Peña-Solórzano ◽  
Vladimir V. Kouznetsov ◽  
Cristian Ochoa-Puentes
Keyword(s):  
Physicochemical Properties ◽  
Efficient Method ◽  
Zinc Chloride ◽  
Acidic Medium ◽  
Eutectic Mixture ◽  
Environmentally Friendly ◽  
High Yield

An environmentally friendly and efficient method for the synthesis of indeno[2,1-c]quinolines is developed using a urea/zinc chloride eutectic mixture as a green mildly acidic medium.

Rapid and eco-friendly high yield synthesis of dihydroquinazolinones mediated by urea/zinc chloride eutectic mixture

2019 ◽  
Vol 14 ◽  
pp. 100167 ◽  
Author(s):  
Diana Peña-Solórzano ◽  
Carlos E. González Guilombo ◽  
Cristian Ochoa-Puentes
Keyword(s):  
Zinc Chloride ◽  
Eutectic Mixture ◽  
High Yield

scholarly journals General, Divergent Platform for Diastereoselective Synthesis of trans-Cyclooctenes with High Reactivity and Favorable Physiochemical Properties

2021 ◽  
Author(s):  
Jessica E. Pigga ◽  
Julia Rosenberger ◽  
Andrew Jemas ◽  
Samantha Boyd ◽  
Olga Dmitrenko ◽  
...  
Keyword(s):  
Physicochemical Properties ◽  
Large Scale ◽  
High Reactivity ◽  
Diels Alder ◽  
Synthetic Methods ◽  
High Yield ◽  
Physiochemical Properties ◽  
New Class ◽  
State Models

<p><i>trans</i>-Cyclooctenes (TCOs) are essential partners for the fastest known bioorthogonal reactions, but current synthetic methods are limited by poor diastereoselectivity. Especially hard to access are hydrophilic TCOs with favorable physicochemical properties for live cell or <i>in vivo </i>experiments. Described is a new class of TCOs, ‘a-TCOs’, that is prepared in high yield via stereocontrolled 1,2-additions of nucleophiles to trans-cyclooct-4-enone, which itself was prepared on large scale in two steps from 1,5-cyclooctadiene. Computational transition state models rationalize the diastereoselectivity of 1,2-additions to deliver a-TCO products, which were also shown to be more reactive than standard TCOs and less hydrophobic than even a <i>trans</i>-oxocene analog. Illustrating the favorable physicochemical properties of a-TCOs, a fluorescent TAMRA derivative in live HeLa cells was shown to be cell-permeable through intracellular Diels-Alder chemistry and to washout more rapidly than other TCOs.</p>

scholarly journals General, Divergent Platform for Diastereoselective Synthesis of trans-Cyclooctenes with High Reactivity and Favorable Physiochemical Properties

2021 ◽  
Author(s):  
Jessica E. Pigga ◽  
Julia Rosenberger ◽  
Andrew Jemas ◽  
Samantha Boyd ◽  
Olga Dmitrenko ◽  
...  
Keyword(s):  
Physicochemical Properties ◽  
Large Scale ◽  
High Reactivity ◽  
Diels Alder ◽  
Synthetic Methods ◽  
High Yield ◽  
Physiochemical Properties ◽  
New Class ◽  
State Models

<p><i>trans</i>-Cyclooctenes (TCOs) are essential partners for the fastest known bioorthogonal reactions, but current synthetic methods are limited by poor diastereoselectivity. Especially hard to access are hydrophilic TCOs with favorable physicochemical properties for live cell or <i>in vivo </i>experiments. Described is a new class of TCOs, ‘a-TCOs’, that is prepared in high yield via stereocontrolled 1,2-additions of nucleophiles to trans-cyclooct-4-enone, which itself was prepared on large scale in two steps from 1,5-cyclooctadiene. Computational transition state models rationalize the diastereoselectivity of 1,2-additions to deliver a-TCO products, which were also shown to be more reactive than standard TCOs and less hydrophobic than even a <i>trans</i>-oxocene analog. Illustrating the favorable physicochemical properties of a-TCOs, a fluorescent TAMRA derivative in live HeLa cells was shown to be cell-permeable through intracellular Diels-Alder chemistry and to washout more rapidly than other TCOs.</p>

Flavan derivatives. XXIII. Preparation and synthetic applications of Flav-3-enes

1968 ◽  
Vol 21 (9) ◽  
pp. 2247 ◽  
Author(s):  
JW Clark-Lewis ◽  
RW Jemison
Keyword(s):  
Sodium Borohydride ◽  
Acidic Medium ◽  
Catalytic Reduction ◽  
Heterocyclic Ring ◽  
High Yield ◽  
Lithium Aluminium Hydride ◽  
Lower Field ◽  
Field Characteristic ◽  
Lithium Aluminium ◽  
New Synthesis

2'-Hydroxychalcones and α-alkoxy-2'-hydroxychalcones are converted by sodium borohydride in isopropanol into flav-3-enes and 3-alkoxyflav-3-enes in the convenient new synthesis which makes these flavenes readily available. Catalytic reduction of the flavenes gives the corresponding flavans or 3-alkoxyflavans in high yield, and the latter are obtained mainly in the 2,s-cis-form. The flavenes immediately give flavs lium cations in the cold when treated with acids in air, and oxidation of 5,7,3',4'-tetramethoxyflav-3-ene with benzoquinone in an acidic medium gave the flavylium salt, isolated as the ferrichloride. Reduction of 5,7,3',4'-tetramethoxy-flavylium chloride with lithium aluminium hydride gave 5,7,3',4'-tetramethoxy-flav-2-ene identical with the flavene obtained from (-)-epicatechin tetramethyl ether, and confirms an earlier investigation by Gramshaw, Johnson, and King. In its N.M.R. spectrum the heterocyclic-ring protons of this flav-2-ene give an ABX multiplet which is easily distinguished from the ABX multiplet at much lower field characteristic of flav-3-enes.

scholarly journals N-acylation of amides through internal nucleophilic catalysis

2020 ◽  
pp. 174751982092575
Author(s):  
Meng Yao ◽  
Xia Chen ◽  
Yuling Lu ◽  
Zhenhua Guan ◽  
Zengwei Luo ◽  
...  
Keyword(s):  
Natural Products ◽  
Efficient Method ◽  
Pyridine Ring ◽  
Environmentally Friendly ◽  
Biologically Active ◽  
Active Materials ◽  
Nucleophilic Catalysis

An efficient method for N-acylation of amides is described using a pyridine ring as the internal nucleophilic catalyst to give imides in moderate to excellent yields. The methodology provides a facile, air insensitive, and environmentally friendly route to form diversified imide scaffolds, which exist widely in natural products and biologically active materials.

Effect of reactive organoclay on physicochemical properties of vegetable oil-based waterborne polyurethane nanocomposites

RSC Advances ◽  
2015 ◽  
Vol 5 (15) ◽  
pp. 11524-11533 ◽  
Author(s):  
T. Gurunathan ◽  
Smita Mohanty ◽  
Sanjay K. Nayak
Keyword(s):  
Physicochemical Properties ◽  
Vegetable Oil ◽  
Castor Oil ◽  
Environmentally Friendly ◽  
Waterborne Polyurethane ◽  
Isophorone Diisocyanate ◽  
Polyurethane Nanocomposites

The environmentally friendly vegetable oil-based waterborne polyurethane–organoclay nanocomposites have been successfully synthesized from castor oil polyols, isophorone diisocyanate and dimethylolpropionic acid.

Novel ferrocene-based bifunctional amine–thioureas for asymmetric Michael addition of acetylacetone to nitroolefins

2015 ◽  
Vol 13 (17) ◽  
pp. 5054-5060 ◽  
Author(s):  
Xiaochen Ren ◽  
Chunyan He ◽  
Yingle Feng ◽  
Yonghai Chai ◽  
Wei Yao ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Efficient Method ◽  
Michael Addition ◽  
High Yield ◽  
Bifunctional Catalysts ◽  
Michael Adducts ◽  
Asymmetric Michael Addition ◽  
Multiple Hydrogen Bonding

An efficient method was developed to synthesize the ferrocene-based bifunctional amine–thioureas bearing multiple hydrogen-bonding donors. Asymmetric Michael addition of acetylacetone to nitroolefins catalyzed by these novel bifunctional catalysts affords the Michael adducts in high yield and moderate to excellent enantioselectivities.

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