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You searched for: Subject chemical reactions Remove constraint Subject: chemical reactions Subject phenylacetic acid Remove constraint Subject: phenylacetic acid
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1. (−)-(2S,3R,Z)-Nakinadine A: First Asymmetric Synthesis and Absolute Configuration Assignment

Author:
Davies Stephen G.; Fletcher Ai M.; Roberts Paul M.; Shah Rushabh S.; Thompson Amber L.; Thomson James E.
Source:
Organic letters 2014 v.16 no.5 pp. 1354-1357
ISSN:
1523-7052
Subject:
chemical reactions; chemical structure; imines; phenylacetic acid; spectroscopy
Abstract:
... Mannich-type reaction of methyl phenylacetate with the N-tert-butylsulfinyl imine derived from (R)-tert-butylsulfinamide and (Z)-14-(pyridin-3′-yl)tetradec-11-enal has been used as the key step in the first asymmetric synthesis of (−)-nakinadine A. Both the 2,3-syn- and 2,3-anti-diastereoisomers were prepared; comparison of spectroscopic and specific rotation data facilitated assignment of the abs ...
DOI:
10.1021/ol500096r

2. Beneficial effect of carboxylic acid additives on the Pd-catalyzed intramolecular N-arylation of 2-amino-3-(2-chlorophenylsulfonyl)pyrroles

Author:
Perounsack X. Moon; Chad E. Stephens
Source:
Tetrahedron letters 2013 v.54 pp. 6226-6229
ISSN:
0040-4039
Subject:
acetic acid; additives; chemical reactions; chemical structure; phenylacetic acid; pyrroles
Abstract:
... Carboxylic acid additives have been shown to significantly improve the yield of the Pd-catalyzed intramolecular N-arylation of 2-aminopyrroles containing a 2-chlorophenylsulfonyl group at the 3-position to give a novel tricyclic ring system. Pivalic and phenylacetic acid provided the best yield enhancement, while acetic acid showed moderate enhancement. Other acids showed limited to no enhancement ...
DOI:
10.1016/j.tetlet.2013.09.011

3. Efficient removal of both basic and non-basic nitrogen compounds from fuels by deep eutectic solvents

Author:
Mohammad Chand Ali; Qiwei Yang; Andrew Aaron Fine; Wenbin Jin; Zhiguo Zhang; Huabin Xing; Qilong Ren
Source:
Green chemistry 2015 v.18 no.1 pp. 157-164
ISSN:
1463-9270
Subject:
chemical reactions; choline; fuels; green chemistry; heptane; oils; phenylacetic acid; pyridines; solvents; sulfur; temperature
Abstract:
... The removal of nitrogen compounds (N-compounds) from fuels has attracted considerable attention because of the necessity to reduce nitrogen oxide emission and improve sulfur elimination. In this work, we reported a novel denitrogenation method of fuels using deep eutectic solvents (DESs) as extractants, and demonstrated the essential role of a rational control of the physicochemical character of D ...
DOI:
10.1039/c5gc01823d

4. Enantioselective Total Synthesis of (−)-Incarviatone A

Author:
Hong Benke; Li Chao; Wang Zhen; Chen Jie; Li Houhua; Lei Xiaoguang
Source:
Journal of the American Chemical Society 2015 v.137 no.37 pp. 11946-11949
ISSN:
1520-5126
Subject:
biomimetics; chemical reactions; enantiomers; mechanistic models; phenylacetic acid; synthesis
Abstract:
... We report herein the first total synthesis of (−)-incarviatone A (1) in 14 steps starting from commercially available inexpensive phenylacetic acid (9). Our early stage synthesis relies on the scalable and sequential C–H functionalization to rapidly assemble the indanyl dialdehyde framework. Further biomimetic cascade strategy allows us to obtain the natural product in a one-pot operation. We also ...
DOI:
10.1021/jacs.5b08551

5. Enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction

Author:
P. Veeraraghavan Ramachandran; Prem B. Chanda
Source:
Chemical communications 2013 v.49 no.30 pp. 3152-3154
ISSN:
1364-548X
Subject:
chemical communication; chemical reactions; chromatography; diastereomers; enantioselective synthesis; phenylacetic acid; solvents; temperature
Abstract:
... A reagent-controlled, diastereo- and enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates has been achieved by the proper choice of solvent, temperature, alkoxy group, and amine for the diisopinocampheylboron-mediated asymmetric enolization–aldolization of phenylacetates. The pure diastereomers can be readily separated by column chromatography. ...
DOI:
10.1039/c3cc40860d

6. Enantioselective synthesis of levomilnacipran

Author:
Julien Alliot; Edmond Gravel; Florence Pillon; David-Alexandre Buisson; Marc Nicolas; Eric Doris
Source:
Chemical communications 2012 v.48 no.65 pp. 8111-8113
ISSN:
1364-548X
Subject:
antidepressants; chemical communication; chemical reactions; enantioselective synthesis; phenylacetic acid
Abstract:
... A novel approach for the asymmetric synthesis of the active (1S,2R)-enantiomer of the antidepressant milnacipran is reported. The two stereogenic centers borne by the cyclopropane ring were sequentially installed starting from phenylacetic acid. ...
DOI:
10.1039/c2cc33743f

7. Heteropoly acid as a novel efficient catalyst for Fries rearrangement

Author:
Elena F. Kozhevnikova; Eric G. Derouane; Ivan V. Kozhevnikov
Source:
Chemical communications 2002 v. no.11 pp. 1178-1179
ISSN:
1364-548X
Subject:
catalysts; chemical reactions; phenylacetic acid
Abstract:
... Heteropoly acid H₃PW₁₂O₄₀ is a very efficient and environmentally benign catalyst for the Fries rearrangement of phenyl acetate in homogeneous or heterogeneous liquid-phase systems at 100–150 °C. ...
DOI:
10.1039/b202148j

8. Legonoxamines A-B, two new hydroxamate siderophores from the soil bacterium, Streptomyces sp. MA37

Author:
Fleurdeliz Maglangit; Ming Him Tong; Marcel Jaspars; Kwaku Kyeremeh; Hai Deng
Source:
Tetrahedron letters 2019 v.60 no.1 pp. 75-79
ISSN:
0040-4039
Subject:
Streptomyces; biochemical pathways; bioinformatics; biosynthesis; cadaverine; chemical reactions; deferoxamine; moieties; multigene family; nuclear magnetic resonance spectroscopy; phenylacetic acid; siderophores; soil bacteria
Abstract:
... Two new siderophores belonging to the hydroxamate class, Legonoxamine A (1) and B (2) have been isolated from the soil bacterium, Streptomyces sp. MA37, together with one known compound, desferrioxamine B (3). Their structures were elucidated based on spectroscopic methods including 1D, 2D NMR, MS, as well as by comparison with the relevant literatures. To our knowledge, this is the first report d ...
DOI:
10.1016/j.tetlet.2018.11.063

9. Meta-Selective Arene C–H Bond Olefination of Arylacetic Acid Using a Nitrile-Based Directing Group

Author:
Bera Milan; Modak Atanu; Patra Tuhin; Maji Arun; Maiti Debabrata
Source:
Organic letters 2014 v.16 no.21 pp. 5760-5763
ISSN:
1523-7052
Subject:
aromatic hydrocarbons; catalytic activity; chemical bonding; chemical reactions; drugs; moieties; palladium; phenylacetic acid
Abstract:
... A nitrile-based template attached with a phenylacetic acid framework promoted meta-selective C–H bond olefination. This palladium-catalyzed protocol is applicable to a wide range of substituted phenylacetic acids and tolerates a variety of functional groups. The versatility of this operationally simple method has been demonstrated through drug diversification. ...
DOI:
10.1021/ol502823c

10. Non-planar oligoarylene macrocycles from biphenyl

Author:
Antoine Robert; Pierre Dechambenoit; Elisabeth A. Hillard; Harald Bock; Fabien Durola
Source:
Chemical communications 2017 v.53 no.84 pp. 11540-11543
ISSN:
1364-548X
Subject:
biphenyl; chemical reactions; phenanthrenes; phenylacetic acid
Abstract:
... Saddle- and propeller-shaped macrocycles are obtained by fourfold Perkin condensations in transient high dilution of 4,4′-bis(phenylglyoxylic acid) with either 4,4′-bis(phenylacetic acid) or p-phenylenediacetic acid, followed by four-fold oxidative photocyclizations. In the saddle-shaped tetraphenanthrylene, the angle between opposite phenanthrene planes is close to the value of 90° of an ideal sa ...
DOI:
10.1039/c7cc06798d

11. Novel synthesis of benzofuran- and indol-2-yl-methanamine derivatives

Author:
Joachim Schlosser; Eugen Johannes; Melanie Zindler; Jan Lemmerhirt; Benjamin Sommer; Martin Schütt; Christian Peifer
Source:
Tetrahedron letters 2015 v.56 no.1 pp. 89-94
ISSN:
0040-4039
Subject:
chemical reactions; hydrobromic acid; hydrochloric acid; indoles; moieties; phenylacetic acid
Abstract:
... We report on a novel synthesis towards benzofuran-2-yl-methanamine and indol-2-yl-methanamine derivatives by using ortho-methoxy and ortho-nitro substituted phenylacetic acids as starting material, respectively. For each compound series, a key intermediate bearing the oxazole-4-carboxylic acid methylester moiety was produced. Refluxing the ortho-methoxy series in HBr/HAc produced the desired benzo ...
DOI:
10.1016/j.tetlet.2014.11.015

12. Nucleophilic reactivities of Schiff base derivatives of amino acids

Author:
Daria S. Timofeeva; Armin R. Ofial; Herbert Mayr
Source:
Tetrahedron 2019 v.75 no.4 pp. 459-463
ISSN:
0040-4020
Subject:
Lewis acids; Lewis bases; amino acids; benzophenones; chemical reactions; chemical structure; dimethyl sulfoxide; energy; esters; phenylacetic acid; potassium; quinones; schiff bases
Abstract:
... Treatment of α-imino esters derived from glycine esters and benzophenone or benzaldehydes with potassium tert butoxide in DMSO gave persistent solutions of carbanions at 20 °C. The kinetics of their reactions with quinone methides and benzylidene malonates (reference electrophiles) have been followed photometrically under pseudo-first order conditions. The reactions followed second-order rate laws ...
DOI:
10.1016/j.tet.2018.11.075

13. Palladium-catalyzed direct ortho-alkynylation of aryl acetamides with low catalyst loading

Author:
Wenjing Li; Hailong Liu; Xue Chen; Shun Li; Renyin Zheng; Chunchun Zhang; Xueli Zheng; Maolin Yuan; Ruixiang Li; Haiyan Fu; Hua Chen
Source:
Tetrahedron letters 2019 v.60 no.29 pp. 1875-1879
ISSN:
0040-4039
Subject:
acetamides; catalysts; catalytic activity; chemical reactions; ligands; moieties; palladium; phenylacetic acid; pyridines
Abstract:
... The palladium-catalyzed alkynylation of phenylacetic acid derivatives using 4-CF3C6F4NH2 as the auxiliary is described. The reaction efficiency can be greatly promoted by pyridine ligand, which enables the reaction to proceed at a catalyst loading as low as 1 mol%. Various functional groups are tolerated under the reaction conditions. The kinetic studies show that the rate of the reaction is first ...
DOI:
10.1016/j.tetlet.2019.06.003

14. Photocontrolled chignolin-derived β-hairpin peptidomimetics

Author:
T. Podewin; M. S. Rampp; I. Turkanovic; K. L. Karaghiosoff; W. Zinth; A. Hoffmann-Röder
Source:
Chemical communications 2015 v.51 no.19 pp. 4001-4004
ISSN:
1364-548X
Subject:
Fourier transform infrared spectroscopy; chemical reactions; nuclear magnetic resonance spectroscopy; peptides; phenolic compounds; phenylacetic acid
Abstract:
... The synthesis of novel, chignolin-derived peptides comprising the azobenzene photoswitch [3-(3-aminomethyl)phenylazo]phenylacetic acid (AMPP) is reported. Reversible photoswitching behavior led to folding into β-hairpin-like structures, as unequivocally demonstrated by CD, FT-IR and NMR spectroscopy. ...
DOI:
10.1039/c4cc10304a

15. Promiscuous activity of C-acyltransferase from Pseudomonas protegens: synthesis of acetanilides in aqueous buffer

Author:
Anna Żądło-Dobrowolska; Nina G. Schmidt; Wolfgang Kroutil
Source:
Chemical communications 2018 v.54 no.27 pp. 3387-3390
ISSN:
1364-548X
Subject:
Pseudomonas protegens; aniline; chemical bonding; chemical reactions; enzyme activity; in vitro studies; phenylacetic acid; transferases
Abstract:
... Amide bond formation has considerable significance in synthetic chemistry. Although the C-acyltransferase from Pseudomonas protegens has been found to catalyze C–C bond formation in nature as well as in in vitro experiments with non-natural substrates, it is now shown that the enzyme is also able to catalyze amide formation using aniline derivatives as substrates with promiscuous activity. Importa ...
DOI:
10.1039/c8cc00290h
PubMed:
29553154
PubMed Central:
PMC5885802

16. Quantitative model studies on the formation of aroma-active aldehydes and acids by Strecker-type reactions

Author:
Hofmann, T.; Munch, P.; Schieberle, P.
Source:
Journal of agricultural and food chemistry 2000 v.48 no.2 pp. 434-440
ISSN:
0021-8561
Subject:
phenylacetic acid; carbonyl compounds; phenylacetaldehyde; chemical reactions; glucose; phenylalanine; odor compounds; heat treatment; odors
Abstract:
... Application of aroma extract dilution analysis on the volatiles formed by reacting glucose and L-phenylalanine (30 min, 100 degrees C) revealed the Strecker aldehyde, phenylacetaldehyde (PA), and, in addition, phenylacetic acid (PAA) as the two key odorants among the volatiles formed. Quantitative measurements on alpha-dicarbonyl formation revealed that the 3-deoxyosone and glyoxal were formed as ...
DOI:
10.1021/jf990954c
PubMed:
10691653

17. Solvent- or Temperature-Controlled Diastereoselective Aldol Reaction of Methyl Phenylacetate

Author:
Ramachandran P. Veeraraghavan; Chanda Prem B.
Source:
Organic letters 2012 v.14 no.17 pp. 4346-4349
ISSN:
1523-7052
Subject:
chemical reactions; chemical structure; diastereoselectivity; methylene chloride; phenylacetic acid; solvents; temperature
Abstract:
... Unlike the enolboration–aldolization of methyl propanoate, the choice of either the solvent or temperature determines the diastereoselectivity during the enolboration–aldolization of methyl phenylacetate. In CH₂Cl₂, the reaction favors the anti-pathway at −78 °C and the syn-pathway at rt. Conversely, the reaction produces the anti-isomer up to rt and the syn-isomer at refluxing temperatures in non ...
DOI:
10.1021/ol301782s

18. An efficiently cobalt-catalyzed carbonylative approach to phenylacetic acid derivatives

Author:
Meng-yao She; Da-wei Xiao; Bing Yin; Zheng Yang; Ping Liu; Jian-li Li; Zhen Shi
Source:
Tetrahedron 2013 v.69 pp. 7264-7268
ISSN:
0040-4020
Subject:
atmospheric pressure; benzimidazole; catalytic activity; chemical reactions; chemical structure; cobalt; computer simulation; phenylacetic acid
Abstract:
... A highly efficient cobalt-catalyzed carbonylative approach to phenylacetic acid derivatives under one atmosphere pressure is reported. This methodology represents a useful extension of benzimidazole used as ligand in metal catalysis, and the catalytic mechanism has been proved by computer simulation. Notably, this new cobalt precatalyst, which promotes the carbonylation reaction dramatically and h ...
DOI:
10.1016/j.tet.2013.06.083

19. meso-Aryl tribenzosubporphyrin—a totally substituted subporphyrin species

Author:
Elena A. Makarova; Soji Shimizu; Atsushi Matsuda; Evgeny A. Luk’yanets; Nagao Kobayashi
Source:
Chemical communications 2008 v. no.18 pp. 2109-2111
ISSN:
1364-548X
Subject:
boric acid; chemical reactions; electrochemistry; phenylacetic acid; phthalimide; spectroscopy
Abstract:
... meso-Aryl tribenzosubporphyrin was synthesized by a self-condensation of 3-benzalphthalimidine and by a condensation of phthalimide with phenylacetic acid using boric acid as a template; the compounds derived were characterized based on a wide range of spectroscopic and electrochemical methods. ...
DOI:
10.1039/b801712c

20. A metal-free protocol for direct oxidative de-alkoxycarbonylation of alkyl phenyl acetate by molecular iodine

Author:
Vivek T. Humne; Pradeep D. Lokhande
Source:
Tetrahedron letters 2014 v.55 no.15 pp. 2337-2339
ISSN:
0040-4039
Subject:
chemical reactions; iodine; moieties; phenylacetic acid; protocols
Abstract:
... A metal-free protocol for the direct oxidative de-alkoxycarbonylation of alkyl phenyl acetate has been carried out by molecular iodine with good yield. In the present Letter, the vital role of iodine in oxidative de-alkoxycarbonylation is described. This method has been proven to be tolerant to a broad range of functional groups. ...
DOI:
10.1016/j.tetlet.2014.02.049