I2-DMSO Mediated Oxidative Amidation of Methyl Ketones with Anthranils for the Synthesis of α-Ketoamides

2021 ◽  
Author(s):  
Shi-Yi Zhuang ◽  
Yong-Xing Tang ◽  
Xiang-Long Chen ◽  
Yan-Dong Wu ◽  
An-Xin Wu
Keyword(s):  
Direct Synthesis ◽  
Methyl Ketones ◽  
Atom Economy ◽  
Metal Free ◽  
Free Process ◽  
Oxidative Amidation

An I2-DMSO mediated oxidative amidation of methyl ketones using anthranils as masked N-nucleophiles has been developed for the direct synthesis of α-ketoamides with high atom-economy. This metal-free process involves reductive...

Direct synthesis of indazole derivatives via Rh(iii)-catalyzed C–H activation of phthalazinones and allenes

2021 ◽  
Vol 19 (35) ◽  
pp. 7701-7705
Author(s):  
Chuanliu Yin ◽  
Tianshuo Zhong ◽  
Xiangyun Zheng ◽  
Lianghao Li ◽  
Jian Zhou ◽  
...  
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Direct Synthesis ◽  
Atom Economy

An Rh(iii)-catalyzed annulation of phthalazinones and various allenes was developed, leading to the formation of indazole derivatives. This catalytic system exhibits excellent functional group tolerance and atom economy.

Electrochemical-induced synthesis of quinazolinones via cathode hydration of o-aminobenzonitriles in aqueous solution

2021 ◽  
Author(s):  
Li Yang ◽  
Huiqing Hou ◽  
Lan Li ◽  
Jin Wang ◽  
Sunying Zhou ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Transition Metal ◽  
Metal Free ◽  
Free Process

An efficient and practical electrochemical-catalyzed transition metal-free process for the synthesis of substituted quinazolinones from simple and readily available o-aminobenzonitriles and aldehydes in water has been accomplished. I2/base and water...

Green synthesis of benzoimidazopyrimidine, benzimidazoloquinazolinone, triazolopyrimidine and triazoloquinazolinone derivatives catalyzed by oxalic acid dihydrate

2021 ◽  
Vol 18 ◽  
Author(s):  
Seyed Sajad Sajadikhah ◽  
Bagher Liravi-Deylami
Keyword(s):  
Oxalic Acid ◽  
Green Synthesis ◽  
Column Chromatography ◽  
Catalytic Amount ◽  
Atom Economy ◽  
One Pot ◽  
Oxalic Acid Dihydrate ◽  
Metal Free ◽  
Solvent Free Conditions ◽  
Simple Filtration

: Benzoimidazopyrimidine, benzimidazoloquinazolinone, triazolopyrimidine, and triazoloquinazolinone derivatives were synthesized via a one-pot multi-component reaction in the presence of a catalytic amount of oxalic acid dihydrate. The reactions were performed in the mixture of EtOH: H2O or under solvent-free conditions as green media. The advantageous features of these methodologies are inexpensive starting materials and catalyst, high atom economy and good yields, and metal-free synthesis. Moreover, all the products were obtained by simple filtration with no need for column chromatography or tedious separation procedures, which is very important in terms of reducing environmental pollutions.

Metal-Free Oxidative Thioesterification of Methyl Ketones with Thiols/Disulfides for the Synthesis of α-Ketothioesters

2018 ◽  
Vol 83 (24) ◽  
pp. 14978-14986 ◽  
Author(s):  
Biao Hu ◽  
Pan Zhou ◽  
Qiaohe Zhang ◽  
Yanqin Wang ◽  
Siyun Zhao ◽  
...  
Keyword(s):  
Methyl Ketones ◽  
Metal Free

scholarly journals Icilio Guareschi and his amazing “1897 reaction”

2021 ◽  
Vol 17 ◽  
pp. 1335-1351
Author(s):  
Gian Cesare Tron ◽  
Alberto Minassi ◽  
Giovanni Sorba ◽  
Mara Fausone ◽  
Giovanni Appendino
Keyword(s):  
Organic Chemistry ◽  
Water Solution ◽  
Applied Science ◽  
History Of Chemistry ◽  
Metal Free ◽  
Free Process ◽  
History Of ◽  
Neutral Water

Organic chemistry honors Icilio Guareschi (1847–1918) with three eponymic reactions, the best known ones being the Guareschi synthesis of pyridones and the Guareschi–Lustgarten reaction. A third Guareschi reaction, the so-called “Guareschi 1897 reaction”, is one of the most unusual reactions in organic chemistry, involving the radical-mediated paradoxical aerobic generation of hydrocarbons in near-neutral water solution. A discussion of the mechanism of this amazing reaction, the only metal-free process that generates hydrocarbons, and the implications of the approach in biology and geosciences mirrors the multifaceted scientific personality of the discoverer. Thus, Guareschi’s eclectic range of activities spans a surprising variety of topics, overcoming the boundaries of the traditional partition of chemistry into organic, inorganic, and analytical branches and systematically crosses the divide between pure and applied science as well as between the history of chemistry and the personal contributions to its development.

Reactions of Methyl Ketones and (Hetero)arylcarboxamides with N,N-Dimethylacetamide Dimethyl Acetal. A Simple Metal-Free Synthesis of 2,4,6-Trisubstituted Pyridines

2015 ◽  
Vol 68 (2) ◽  
pp. 184 ◽  
Author(s):  
Benjamin Prek ◽  
Uroš Grošelj ◽  
Marta Kasunič ◽  
Silvo Zupančič ◽  
Jurij Svete ◽  
...  
Keyword(s):  
Microwave Irradiation ◽  
Single Crystal ◽  
Ammonium Acetate ◽  
Dimethyl Acetal ◽  
Methyl Ketones ◽  
Closed Vessel ◽  
Simple Metal ◽  
One Pot ◽  
X Ray ◽  
Metal Free

Two metal-free syntheses of 2,4,6-trisubstituted pyridines 10a–m and 16a–j are described. N,N,6-Trimethyl-4-(substituted)pyridin-2-amines 10 were prepared from aryl or heteroaryl methyl ketones which were transformed with N,N-dimethylacetamide dimethyl acetal (DMADMA) into enaminones 4a–m, followed by treatment with ammonium acetate to give (Z)-3-amino-1-(substituted)but-2-en-1-ones 5a–m. These were treated with DMADMA under microwave irradiation in a closed vessel at 130°C, to give via intermediates 7–9 the final products 10a–m. N2,N2,N4,N4-Tetramethyl-6-(substituted) pyridine-2,4-diamines 16a–j were prepared in a one-pot synthesis from the corresponding carboxamides 11a–j by treatment with an excess of DMADMA in a closed vessel under microwave irradiation to give via intermediates 12a–j to 15a–j the final products 16a–j. X-Ray single crystal diffractometry studies of the enaminones 5c, 5g, 5i, 5j, and 5m and 2,4,6-trisubstituted pyridines 16a, 16b, 16g, 16i, and 16j were consistent with the expected structures.

Direct Oxidation of Primary Alcohols to Carboxylic Acids

Synthesis ◽  
2020 ◽  
Author(s):  
Travis J. Williams ◽  
Valeriy Cherepakhin
Keyword(s):  
Carboxylic Acids ◽  
Direct Synthesis ◽  
Primary Alcohol ◽  
Alcohol Oxidation ◽  
Atom Economy ◽  
Primary Alcohols ◽  
Direct Oxidation ◽  
Metal Compounds ◽  
New Methods ◽  
Active Research

AbstractOxidation of primary alcohols to carboxylic acids is a fundamental transformation in organic chemistry, yet despite its simplicity, extensive use, and relationship to pH, it remains a subject of active research for synthetic organic chemists. Since 2013, a great number of new methods have emerged that utilize transition-metal compounds as catalysts for acceptorless dehydrogenation of alcohols to carboxylates. The interest in this reaction is explained by its atom economy, which is in accord with the principles of sustainability and green chemistry. Therefore, the methods for the direct synthesis of carboxylic acids from alcohols is ripe for a modern survey, which we provide in this review.1 Introduction2 Thermodynamics of Primary Alcohol Oxidation3 Oxometalate Oxidation4 Transfer Dehydrogenation5 Acceptorless Dehydrogenation6 Electrochemical Methods7 Outlook

PIDA-mediated α-C–H functionalization of enaminones: the synthesis of thiocyano enaminones and chromones in water

2019 ◽  
Vol 43 (42) ◽  
pp. 16441-16444 ◽  
Author(s):  
Zan Yang ◽  
Liping Hu ◽  
Ting Cao ◽  
Li An ◽  
Lijun Li ◽  
...  
Keyword(s):  
Aqueous Medium ◽  
Room Temperature ◽  
Metal Free ◽  
Free Process

Herein, an efficient, metal-free process for the α-C–H thiocyanation of enaminones was developed using PhI(OAc)2 as an oxidant at room temperature in an aqueous medium.

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