Aryl Ketone Mediated Photoinduced Radical Coupling for the Alkylation­ of Benzazoles Employing Saturated Heterocyclic Compounds­

Synthesis ◽  
2019 ◽  
Vol 51 (20) ◽  
pp. 3859-3864 ◽  
Author(s):  
Shin Kamijo ◽  
Kaori Kamijo ◽  
Toshihiro Murafuji
Keyword(s):  
Ambient Temperature ◽  
Heterocyclic Compounds ◽  
Cyclic Ether ◽  
Reaction Conditions ◽  
Neutral Reaction ◽  
Radical Coupling ◽  
Aryl Ketone ◽  
Saturated Heterocycles

An aryl ketone mediated synthesis of 2-alkylated benzazoles was achieved via radical coupling under photoirradiation starting from saturated heterocycles and 2-sulfonylated benzazoles, such as benzothiazoles, benzoxazole, and benzimidazole. Heterocyclic compounds, including a cyclic ether, azacycles, and tetrahydrothiophene, were applicable, and the benzazole unit was site-selectively installed at the carbon center proximal to the heteroatom. The present transformation takes place at ambient temperature under neutral reaction conditions without the aid of any metallic catalysts or reagents.

The chemistry of 4-(dicyanomethylene)-3-methyl-l-phenyl-2-pyrazoline-5- ones as a privileged scaffold in synthesis of heterocycles

2020 ◽  
Vol 17 ◽  
Author(s):  
Mohsen A.-M. Gomaa ◽  
Huda A. Ali
Keyword(s):  
Building Block ◽  
Heterocyclic Compounds ◽  
Recent Progress ◽  
Reaction Conditions ◽  
Azacrown Ethers ◽  
Wide Range ◽  
Privileged Scaffold ◽  
Number Of Publications ◽  
Near Future

Background : The reactivity of 4-(dicyanomethylene)-3-methyl-l-phenyl-2-pyrazoline-5-one DCNP 1 and its derivatives makes it valuable as a building block for the synthesis of heterocyclic compounds like pyrazolo-imidazoles, - thiazoles, spiropyridines, spiropyrroles, spiropyrans and others. As a number of publications have reported on the reactivity of DCNP and its derivatives, we compiled some features of this interesting molecule. Objective: This article aims to review the preparation of DCNP, its reactivity and application in heterocyclic and dyes synthesis. Conclusion: In this review we have provided an overview of recent progress in the chemistry of DCNP and its significance in synthesis of various classes of heterocyclic compounds and dyes. The unique reactivity of DCNP offers unprecedentedly mild reaction conditions for the generation of versatile cynomethylene dyes from a wide range of precursors including amines, α-aminocarboxylic acids, their esters, phenols, malononitriles and azacrown ethers. We anticipate that more innovative transformations involving DCNP will continue to emerge in the near future.

Synthesis of Pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by Alkyne-Carbonyl Metathesis

Synthesis ◽  
2020 ◽  
Author(s):  
Peter Ehlers ◽  
Peter Langer ◽  
Marian Blanco Ponce ◽  
Silvio Parpart ◽  
Alexander Villinger ◽  
...  
Keyword(s):  
Heterocyclic Compounds ◽  
Metathesis Reaction ◽  
Synthetic Methodology ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Metal Free ◽  
Modular Synthesis

AbstractA concise and modular synthesis of pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by a one-pot two-step reaction consisting of electrophilic acylation followed by an alkyne-carbonyl-metathesis reaction as the final cyclization step is reported. This developed synthetic methodology allows the facile synthesis of these heterocyclic core structures in mainly high overall yields under metal-free conditions. Reaction conditions are carefully optimized and display a novel supplement to access these tricyclic heterocyclic compounds.

An efficient multicomponent, one-pot synthesis of Betti bases catalyzed by cerium (IV) ammonium nitrate (CAN) at ambient temperature

2016 ◽  
Vol 5 (4) ◽  
Author(s):  
Ramadan Ahmed Mekheimer ◽  
Abdullah Mohamed Asiri ◽  
Afaf Mohamed Abdel Hameed ◽  
Reham R. Awed ◽  
Kamal Usef Sadek
Keyword(s):  
Ambient Temperature ◽  
Environmental Pollution ◽  
Ammonium Nitrate ◽  
Room Temperature ◽  
Catalytic Amount ◽  
High Yield ◽  
Reaction Conditions ◽  
One Pot ◽  
Work Up ◽  
Cerium Iv Ammonium Nitrate

AbstractStarting from readily available 2-naphthol, aldehydes, aryl and alkylamines, a variety of Betti bases were efficiently synthesized utilizing a catalytic amount of cerium (IV) ammonium nitrate (CAN) at room temperature. This protocol has advantages of high yield, mild reaction conditions, no environmental pollution, diversity of reactants and simple work up procedure.

Metal-free, air-promoted, radical-mediated arylation of benzoquinone with phenylhydrazines

2018 ◽  
Vol 73 (10) ◽  
pp. 703-706 ◽  
Author(s):  
Mohammad Hosein Sayahi ◽  
Samira Ansari ◽  
Seyyed Jafar Saghanezhad ◽  
Mohammad Mahdavi
Keyword(s):  
Ambient Temperature ◽  
Reaction Conditions ◽  
Direct Arylation ◽  
Metal Free ◽  
Free Air ◽  
Pharmaceutical Materials

AbstractAn efficient, economic, and air-promoted metal-free method for direct arylation of benzoquinone with phenylhydrazines was developed. This approach leads to the formation of corresponding [1,1′-biphenyl]-2,5-dione derivatives as biological and pharmaceutical materials of interest in good yields, under mild reaction conditions, and at ambient temperature.

Synthesis of Yuehchukene Analogues, Murrapanine and Normurrapanine Utylizing Thermal Reaction of b-(1-Hydroxybutenyl)indoles under Neutral Reaction Conditions

Heterocycles ◽  
1996 ◽  
Vol 43 (8) ◽  
pp. 1751 ◽  
Author(s):  
Jyh-Horng Sheu ◽  
Yua-Kuang Chen ◽  
Huey-Fen Chung ◽  
Ping-Jyun Sung ◽  
Song-Fong Lin
Keyword(s):  
Thermal Reaction ◽  
Reaction Conditions ◽  
Neutral Reaction

scholarly journals New Products Generated from the Transformations of Ferulic Acid Dilactone

Biomolecules ◽  
2020 ◽  
Vol 10 (2) ◽  
pp. 175 ◽  
Author(s):  
Ying He ◽  
Yuan Jia ◽  
Fachuang Lu
Keyword(s):  
Ferulic Acid ◽  
Succinic Acid ◽  
Plant Cell ◽  
Cell Walls ◽  
New Products ◽  
Plant Cell Walls ◽  
Reaction Conditions ◽  
Radical Coupling ◽  
Naoh Treatment ◽  
Derivatives Of

Various ferulic acid (FA) dimers occurring in plant cell walls, such as 8-5-, 8-O-4-, 5-5-, and 8-8-coupled dimers, are effective antioxidants and potential antimicrobials. It is necessary to access these diferulates as reference compounds to validate those isolated from plants. 3,6-bis(4-hydroxy-3-methoxyphenyl)-tetrahydrofuro-[3,4-c]furan-1,4-dione, a 8-8-coupled FA dilactone generated from ferulic acid via radical coupling, has been used to synthesize 8-8-coupled FA dimers although few reports investigated the distribution of products and mechanisms involved in the transformation of FA dilactone. In this work, the FA dilactone, obtained from FA by a peroxidase-catalyzed radical coupling, was reacted under various base/acid conditions. Effects of reaction conditions and workup procedures on the distribution of products were investigated by GC-MS. The isolated products from such treatments of FA dilactone were characterized by NMR. New derivatives of FA dimer including 2-(4-hydroxy-3-methoxybenzylidene)-3-(hydroxyl-(4-hydroxy-3-methoxyphenyl)methyl)succinic acid and 2-(bis(4-hydroxy-3-methoxyphenyl)-methyl)-succinic acid were produced from NaOH treatment. Another novel 8-8-coupled cyclic FA dimer, diethyl 6-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-methoxy-1,2-dihydronaphthalene-2,3-dicarboxylate was identified in products from FA dilactone treated by dry HCl in absolute ethanol. Mechanisms involved in such transformations were proposed.

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