scholarly journals Recent Advances in the Synthesis of Isocoumarins and Polyaromatic Hydrocarbons for Photoactive Materials

INEOS OPEN ◽  
2021 ◽  
Vol 4 ◽  
Author(s):  
M. A. Arsenov ◽  
◽  
D. A. Loginov ◽  
Keyword(s):  
Aromatic Compounds ◽  
Heterocyclic Compounds ◽  
Polyaromatic Hydrocarbons ◽  
Reaction Products ◽  
Selective Activation ◽  
New Era ◽  
Aromatic Carbon ◽  
Ch Activation ◽  
Photoactive Materials ◽  
Metal Catalyzed

The discovery of transition metal-catalyzed selective activation of aromatic carbon–hydrogen bonds in 1993 has opened a new era in the synthesis of carbo- and heterocyclic compounds. This review covers the applications of oxidative annulations of aromatic compounds with alkynes involving CH activation for the synthesis of isocoumarins and polyaromatic hydrocarbons (PAHs). The limitations, advantages, and mechanical aspects of this approach as well as the current tendencies in the application of the reaction products for photoactive materials are discussed.

Metal-catalyzed regiodivergent organic reactions

2019 ◽  
Vol 48 (16) ◽  
pp. 4515-4618 ◽  
Author(s):  
Carmen Nájera ◽  
Irina P. Beletskaya ◽  
Miguel Yus
Keyword(s):  
Organic Reactions ◽  
Ch Activation ◽  
Allylic Substitutions ◽  
Metal Catalyzed

This review discusses metal-catalysed regiodivergent additions, allylic substitutions, CH-activation, cross-couplings and intra- or intermolecular cyclisations.

scholarly journals Bacterial Conversion of Hydroxylamino Aromatic Compounds by both Lyase and Mutase Enzymes Involves Intramolecular Transfer of Hydroxyl Groups

2003 ◽  
Vol 69 (5) ◽  
pp. 2786-2793 ◽  
Author(s):  
Lloyd J. Nadeau ◽  
Zhongqi He ◽  
Jim C. Spain
Keyword(s):  
Aromatic Compounds ◽  
Ralstonia Eutropha ◽  
Transfer Mechanism ◽  
Bacterial Degradation ◽  
Hydroxyl Group ◽  
Hydroxyl Groups ◽  
Reaction Products ◽  
Comamonas Acidovorans ◽  
Label Incorporation ◽  
Intramolecular Transfer

ABSTRACT Hydroxylamino aromatic compounds are converted to either the corresponding aminophenols or protocatechuate during the bacterial degradation of nitroaromatic compounds. The origin of the hydroxyl group of the products could be the substrate itself (intramolecular transfer mechanism) or the solvent water (intermolecular transfer mechanism). The conversion of hydroxylaminobenzene to 2-aminophenol catalyzed by a mutase from Pseudomonas pseudoalcaligenes JS45 proceeds by an intramolecular hydroxyl transfer. The conversions of hydroxylaminobenzene to 2- and 4-aminophenol by a mutase from Ralstonia eutropha JMP134 and to 4-hydroxylaminobenzoate to protocatechuate by a lyase from Comamonas acidovorans NBA-10 and Pseudomonas sp. strain 4NT were proposed, but not experimentally proved, to proceed by the intermolecular transfer mechanism. GC-MS analysis of the reaction products formed in H2 18O did not indicate any 18O-label incorporation during the conversion of hydroxylaminobenzene to 2- and 4-aminophenols catalyzed by the mutase from R. eutropha JMP134. During the conversion of 4-hydroxylaminobenzoate catalyzed by the hydroxylaminolyase from Pseudomonas sp. strain 4NT, only one of the two hydroxyl groups in the product, protocatechuate, was 18O labeled. The other hydroxyl group in the product must have come from the substrate. The mutase in strain JS45 converted 4-hydroxylaminobenzoate to 4-amino-3-hydroxybenzoate, and the lyase in Pseudomonas strain 4NT converted hydroxylaminobenzene to aniline and 2-aminophenol but not to catechol. The results indicate that all three types of enzyme-catalyzed rearrangements of hydroxylamino aromatic compounds proceed via intramolecular transfer of hydroxyl groups.

scholarly journals Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen

2016 ◽  
Vol 12 ◽  
pp. 144-153 ◽  
Author(s):  
Hans Sterckx ◽  
Johan De Houwer ◽  
Carl Mensch ◽  
Wouter Herrebout ◽  
Kourosch Abbaspour Tehrani ◽  
...  
Keyword(s):  
Molecular Oxygen ◽  
Base Metal ◽  
Iron Catalyst ◽  
Reaction Products ◽  
Metal Impurity ◽  
Alternative Synthesis ◽  
Icp Ms ◽  
Benzylic Oxidation ◽  
Metal Catalyzed ◽  
Methylene Group

The methylene group of various substituted 2- and 4-benzylpyridines, benzyldiazines and benzyl(iso)quinolines was successfully oxidized to the corresponding benzylic ketones using a copper or iron catalyst and molecular oxygen as the stoichiometric oxidant. Application of the protocol in API synthesis is exemplified by the alternative synthesis of a precursor to the antimalarial drug Mefloquine. The oxidation method can also be used to prepare metabolites of APIs which is illustrated for the natural product papaverine. ICP–MS analysis of the purified reaction products revealed that the base metal impurity was well below the regulatory limit.

scholarly journals The soluble methane mono-oxygenase of Methylococcus capsulatus (Bath). Its ability to oxygenate n-alkanes, n-alkenes, ethers, and alicyclic, aromatic and heterocyclic compounds

1977 ◽  
Vol 165 (2) ◽  
pp. 395-402 ◽  
Author(s):  
J Colby ◽  
D I Stirling ◽  
H Dalton
Keyword(s):  
Aromatic Compounds ◽  
Heterocyclic Compounds ◽  
Catalytic Properties ◽  
Methylococcus Capsulatus ◽  
Methylosinus Trichosporium ◽  
Styrene Epoxide ◽  
Cyclic Alkanes ◽  
Methylomonas Albus ◽  
Terminal Oxidation ◽  
Methylomonas Methanica

1. Methane mono-oxygenase of Methylococcus capsulatus (Bath) catalyses the oxidation of various substituted methane derivatives including methanol. 2. It is a very non-specific oxygenase and, in some of its catalytic properties, apparently resembles the analogous enzyme from Methylomonas methanica but differs from those found in Methylosinus trichosporium and Methylomonas albus. 3. CO is oxidized to CO2. 4. C1-C8 n-alkanes are hydroxylated, yielding mixtures of the corresponding 1- and 2-alcohols; no 3- or 4-alcohols are formed. 5. Terminal alkenes yield the corresponding 1,2-epoxides. cis- or trans-but-2-ene are each oxidized to a mixture of 2,3-epoxybutane and but-2-en-1-ol with retention of the cis or trans configuration in both products; 2-butanone is also formed from cis-but-2-ene only. 6. Dimethyl ether is oxidized. Diethyl ether undergoes sub-terminal oxidation, yielding ethanol and ethanal in equimolar amounts. 7. Methane mono-oxygenase also hydroxylates cyclic alkanes and aromatic compounds. However, styrene yields only styrene epoxide and pyridine yields only pyridine N-oxide. 8. Of those compounds tested, only NADPH can replace NADH as electron donor.

Transition metal-catalyzed reactions in heterocyclic chemistry

2002 ◽  
Vol 74 (8) ◽  
pp. 1327-1337 ◽  
Author(s):  
Irina P. Beletskaya
Keyword(s):  
Transition Metal ◽  
Heterocyclic Compounds ◽  
Heterocyclic Chemistry ◽  
Substitution Reactions ◽  
Multiple Bonds ◽  
Palladium Catalyzed ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

The palladium-catalyzed substitution reactions forming carbon­carbon and carbon­element bonds, as well as nickel-catalyzed addition of E­H and E­E' bonds across multiple bonds, are considered in their application to the chemistry of heterocyclic compounds.

Antioxidative activity of heterocyclic compounds formed in Maillard reaction products

2002 ◽  
Vol 1245 ◽  
pp. 335-340 ◽  
Author(s):  
Kenichi Yanagimoto ◽  
Kwang-Geun Lee ◽  
Hirotomo Ochi ◽  
Takayuki Shibamoto
Keyword(s):  
Maillard Reaction ◽  
Heterocyclic Compounds ◽  
Antioxidative Activity ◽  
Maillard Reaction Products ◽  
Reaction Products

scholarly journals Aromatic Hydrocarbon Removal by Novel Extremotolerant Exophiala and Rhodotorula Spp. from an Oil Polluted Site in Mexico

2020 ◽  
Vol 6 (3) ◽  
pp. 135 ◽  
Author(s):  
Martín R. Ide-Pérez ◽  
Maikel Gilberto Fernández-López ◽  
Ayixon Sánchez-Reyes ◽  
Alfonso Leija ◽  
Ramón Alberto Batista-García ◽  
...  
Keyword(s):  
Aromatic Hydrocarbons ◽  
Aromatic Compounds ◽  
High Salinity ◽  
Polyaromatic Hydrocarbons ◽  
Carbon Sources ◽  
Optimal Growth ◽  
Polluted Site ◽  
Removal Capacity ◽  
Wide Range ◽  
Hydrocarbon Removal

Since Aromatic hydrocarbons are recalcitrant and toxic, strategies to remove them are needed. The aim of this work was to isolate fungi capable of using aromatic hydrocarbons as carbon sources. Two isolates from an oil polluted site in Mexico were identified through morphological and molecular markers as a novel Rhodotorula sp. and an Exophiala sp. Both strains were able to grow in a wide range of pH media, from 4 to 12, showing their optimal growth at alkaline pH’s and are both halotolerant. The Exophiala strain switched from hyphae to yeast morphotype in high salinity conditions. To the best of our knowledge, this is the first report of salt triggering dimorphism. The Rhodotorula strain, which is likely a new undescribed species, was capable of removing singled ringed aromatic compounds such as benzene, xylene, and toluene, but could not remove benzo[a] pyrene nor phenanthrene. Nevertheless, these hydrocarbons did not impair its growth. The Exophiala strain showed a different removal capacity. It could remove the polyaromatic hydrocarbons but performed poorly at removing toluene and xylene. Nevertheless, it still could grow well in the presence of the aromatic compounds. These strains could have a potential for aromatic compounds removal.

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