Synthesis of heterocyclic compounds through nucleophilic phosphine catalysis

2020 ◽  
Vol 56 (97) ◽  
pp. 15235-15281
Author(s):  
Yifan Huang ◽  
Jianning Liao ◽  
Wei Wang ◽  
Honglei Liu ◽  
Hongchao Guo
Keyword(s):  
Heterocyclic Compounds ◽  
Environmentally Friendly ◽  
Reaction Conditions ◽  
Metal Free ◽  
Phosphine Catalysis

Nucleophilic phosphine catalysis is a practical and powerful tool for the synthesis of various heterocyclic compounds with the advantages of environmentally friendly, metal-free, and mild reaction conditions.

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.

scholarly journals Recent Advances in Transition-Metal-Free Late-Stage C-H and N-H Arylation of Heteroarenes Using Diaryliodonium Salts

2021 ◽  
Vol 14 (7) ◽  
pp. 661
Author(s):  
Thierry Besson ◽  
Corinne Fruit
Keyword(s):  
Transition Metal ◽  
Late Stage ◽  
Heterocyclic Compounds ◽  
Environmentally Friendly ◽  
Direct Arylation ◽  
Stepping Stone ◽  
Metal Free ◽  
Bond Forming ◽  
Diaryliodonium Salts ◽  
Recent Advances

Transition-metal-free direct arylation of C-H or N-H bonds is one of the key emerging methodologies that is currently attracting tremendous attention. Diaryliodonium salts serve as a stepping stone on the way to alternative environmentally friendly and straightforward pathways for the construction of C-C and C-heteroatom bonds. In this review, we emphasize the recent synthetic advances of late-stage C(sp2)-N and C(sp2)-C(sp2) bond-forming reactions under metal-free conditions using diaryliodonium salts as arylating reagent and its applications to the synthesis of new arylated bioactive heterocyclic compounds.

Transition metal-free α-methylation of 1,8-naphthyridine derivatives using DMSO as methylation reagent

2019 ◽  
Vol 17 (31) ◽  
pp. 7416-7424 ◽  
Author(s):  
Shaohua Jiang ◽  
Zhihai Yang ◽  
Ziyin Guo ◽  
Yibiao Li ◽  
Lu Chen ◽  
...  
Keyword(s):  
Carbon Source ◽  
Transition Metal ◽  
Environmentally Friendly ◽  
Practical Approach ◽  
Reaction Conditions ◽  
Metal Free

A practical approach to the direct α-methylation of 1,8-naphthyridines under mild reaction conditions has been developed using simple and readily available DMSO as a convenient and environmentally friendly carbon source.

scholarly journals Electrochemical Umpolung of Bromide: Transition-Metal-Free Bromination of Indole C–H Bond

Molecules ◽  
2019 ◽  
Vol 24 (4) ◽  
pp. 696 ◽  
Author(s):  
Pan Zhang ◽  
Jianbin Chen ◽  
Wei Gao ◽  
Yiting Xiao ◽  
Changwei Liu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Electrode Material ◽  
Environmentally Friendly ◽  
Transition Metal Catalysts ◽  
Reaction Conditions ◽  
Metal Free ◽  
Chemical Oxidants ◽  
Bromide Ion ◽  
Environmentally Friendly Approach ◽  
Graphite Rod

A facile and sustainable electrochemical umpolung of bromide ion protocol was developed under mild reaction conditions. Transition metal catalysts and exogenous chemical oxidants were obviated for the bromination of C–H bond. Notably, graphite rod, which is commercially available at supermarkets and is inexpensive, was employed as the electrode material. This operationally easy and environmentally friendly approach accomplished the synthesis of 3-bromoindole in excellent yield and regioselectivity.

Iridium-Catalyzed Direct Cyclization of Aromatic Amines with Diols

Synlett ◽  
2018 ◽  
Vol 29 (18) ◽  
pp. 2385-2389 ◽  
Author(s):  
Maki Minakawa ◽  
Kouichi Watanabe ◽  
Satoru Toyoda ◽  
Yasuhiro Uozumi
Keyword(s):  
Aromatic Amines ◽  
Heterocyclic Compounds ◽  
Environmentally Friendly ◽  
Similar Reaction ◽  
Reaction Conditions

We developed an environmentally friendly iridium-catalyzed direct cyclization of aromatic amines with diols that generates the corresponding N-heterocyclic compounds with water as the sole by-product. Thus, under conditions of 165 °C for 18 hours, the direct cyclization of N-methylanilines with 1,3-propanediol by using an IrCl3 catalyst with rac-BINAP as a ligand in mesitylene afforded the corresponding tetrahydroquinoline derivatives with yields ranging from 73 to 83%. ­Under similar reaction conditions, direct cyclization of anilines with 1,3-propanediol produced the corresponding tetrahydrobenzoquinolizine derivatives with yields ranging from 26 to 76%.

p-Sulfonic acid calix[n]arene catalyzed synthesis of bioactive heterocycles: A review

2020 ◽  
Vol 24 ◽  
Author(s):  
Bubun Banerjee ◽  
Gurpreet Kaur ◽  
Navdeep Kaur
Keyword(s):  
Supramolecular Chemistry ◽  
Sulfonic Acid ◽  
Catalytic Efficiency ◽  
The Other ◽  
Reaction Conditions ◽  
Metal Free ◽  
Bioactive Scaffolds ◽  
Wide Range ◽  
Efficient Alternative ◽  
Bioactive Heterocycles

: Metal-free organocatalysts are becoming an important tool for the sustainable developments of various bioactive heterocycles. On the other hand, during last two decades, calix[n]arenes have been gaining considerable attention due to their wide range of applicability in the field of supramolecular chemistry. Recently, sulfonic acid functionalized calix[n] arenes are being employed as an efficient alternative catalyst for the synthesis of various bioactive scaffolds. In this review we have summarized the catalytic efficiency of p-sulfonic acid calix[n]arenes for the synthesis of diverse biologically promising scaffolds under various reaction conditions. There is no such review available in the literature showing the catalytic applicability of p-sulfonic acid calix[n]arenes. Therefore, we strongly believe that this review will surely attract those researchers who are interested about this fascinating organocatalyst.

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.

Chlorination of Arylaldehyde-Derived Arylsulfonylhydrazones with N-Chlorosuccinimide Leading to 1,2,4,5-Tetrazine Derivatives

Synthesis ◽  
2019 ◽  
Vol 52 (01) ◽  
pp. 69-74
Author(s):  
Yuan-Zhao Ji ◽  
Hui-Jing Li ◽  
Ying Liu ◽  
Yan-Chao Wu
Keyword(s):  
Potassium Hydroxide ◽  
Reaction Conditions ◽  
Metal Free ◽  
Vinyl Halides

It has been reported previously that treatment of aryl­ketone-derived arylsulfonylhydrazones with NXS/(nBu)4NX affords exclusively vinyl halides. In contrast, we have found that treatment of aryl­aldehyde-derived arylsulfonylhydrazones with N-chlorosuccinimide in the presence of potassium hydroxide affords 1,2,4,5-tetrazine derivatives in good to excellent yields. The present reactions are carried out under metal-free and mild reaction conditions.

scholarly journals Metal-Free Air Oxidation in a Convenient Cascade Approach for the Access to Isoquinoline-1,3,4(2H)-triones

Molecules ◽  
2019 ◽  
Vol 24 (11) ◽  
pp. 2177
Author(s):  
Antonia Di Mola ◽  
Consiglia Tedesco ◽  
Antonio Massa
Keyword(s):  
Heterocyclic Compounds ◽  
Aromatic Ketone ◽  
Primary Amines ◽  
Cascade Process ◽  
Staudinger Reaction ◽  
Caspase Inhibitor ◽  
Air Oxidation ◽  
Metal Free ◽  
Free Air

Herein we describe a very useful application of the readily available trifunctional aromatic ketone methyl-2-(2-bromoacetyl)benzoate in reactions with primary amines. An unexpected in situ air oxidation that follows a cascade process allowed the access to a series of isoquinoline-1,3,4(2H)-triones, a class of heterocyclic compounds of great interest containing an oxygen-rich heterocyclic scaffold. A modification of the original protocol, utilizing a Staudinger reaction in the presence of trimethylphosphine, was necessary for the synthesis of Caspase inhibitor trione with free NH group.

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