Organocatalytic Combinatorial Synthesis of Quinazoline, Quinoxaline and Bis(indolyl)methanes

2020 ◽  
Vol 23 (1) ◽  
pp. 83-88
Author(s):  
Fatemeh Malamiri ◽  
Samad Khaksar ◽  
Rashid Badri ◽  
Elham Tahanpesar
Keyword(s):  
Green Chemistry ◽  
Heterocyclic Compounds ◽  
Combinatorial Synthesis ◽  
Melting Points ◽  
Reaction Conditions ◽  
Practical Procedure ◽  
Ammonium Hexafluorophosphate

Aim and Objective: An efficient and practical procedure for the synthesis of heterocyclic compounds such as quinazolines, quinoxalines and bis(indolyl)methanes was developed using 3,5-bis(trifluoromethyl) phenyl ammonium hexafluorophosphate (BFPHP) as a novel organocatalyst. Material and Method: All of the obtained products are known compounds and identified by IR, 1HNMR, 13CNMR and melting points. Results: Various products were obtained in good to excellent yields under reaction conditions. Conclusion: The BFPHP organocatalyst demonstrates a novel class of non-asymmetric organocatalysts, which has gained much attention in green chemistry.

Microwave Induced Green chemistry approach towards synthesis of heterocyclic compounds via C-N Bond Forming Reactions

2021 ◽  
Vol 08 ◽  
Author(s):  
Bimal Krishna Banik ◽  
Biswa Mohan Sahoo ◽  
BVV Ravi Kumar ◽  
Krishna Chandra Panda
Keyword(s):  
Green Chemistry ◽  
Ring Opening ◽  
Heterocyclic Compounds ◽  
Unique Feature ◽  
Ring Closure ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Formation Reaction ◽  
Bond Forming ◽  
Bond Forming Reactions

: The synthesis of heterocyclic compounds via carbon-nitrogen (C-N) bond formation reaction is considered as an emerged and efficient protocol in the field of synthetic chemistry. The C–N bond-forming reactions can proceed through condensation, coupling, ring-opening, cyclization or ring closure process etc. The reactivity pattern of these reactions mainly depends upon the reaction conditions as well as the type of catalysts and reacting substances that are associated with the synthesis of heterocyclic compounds containing the C-N system including pyrazole, imidazole, pyridine, pyrimidine, thiazole, tetrazole, isoxazole, benzothiazine and benzimidazole etc. Further, the technique of microwave-induced synthesis becomes an alternative strategy for the sustainable production of structurally diverse organic compounds. This method provides a cleaner reaction, faster reaction rate, atom economy and energy-efficient. So, the utilization of microwave radiation in organic synthesis becomes resource-friendly and eco-friendly processes. It follows the green chemistry approach by using safer solvents, renewable starting materials and green catalysts. The unique feature of this method is to generate various types of bioactive or medicinal agents.

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 protocol for the synthesis of highly sensitive indole imines utilizing green chemistry: optimization of reaction conditions

2018 ◽  
Vol 22 (3) ◽  
pp. 709-722
Author(s):  
Bushra Nisar ◽  
Syeda Laila Rubab ◽  
Abdul Rauf Raza ◽  
Sobia Tariq ◽  
Ayesha Sultan ◽  
...  
Keyword(s):  
Green Chemistry ◽  
Reaction Conditions ◽  
Highly Sensitive

scholarly journals Synthesis of some Heterocyclic Compounds Derived from 2-Chloro-N-p-Tolylacetamide

2017 ◽  
Vol 27 (4) ◽  
Author(s):  
Hanan Gh Shaaban
Keyword(s):  
Heterocyclic Compounds ◽  
Acetyl Chloride ◽  
Aromatic Aldehydes ◽  
Melting Points ◽  
Ft Ir ◽  
Ethyl Amine

This research includes preparation of (2-chloro-N-p-tolylacetamide) (1) from the reaction of (p-aminotoluene) with chloro acetyl chloride. Compound (1) reacted with thiosemi carbazide and gave compound (2), and when compound (1) reacted with semicarbazide gave compound (3). While when compound (1) reacted with thiourea it produced compound (4).Compounds (2-4) when reacted with appropriate aromatic aldehydes or ketones produced Shiff bass (5-16), which in turn reacted with chloro acetyl chloride in the present of tri ethyl amine and dioxin gave β-lactam derivatives (14-22). The structures of these compounds were characterized from their melting points, FT-IR, and NMR. 

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.

Iron-catalyzed radical cascade 6-endo cyclization of dienes towards fused nitrogen heterocycles initiated by an alkoxycarbonyl radical

2020 ◽  
Vol 18 (36) ◽  
pp. 7086-7089
Author(s):  
Shanshan Qiao ◽  
Peng-Cheng Qian ◽  
Fan Chen ◽  
Jiang Cheng
Keyword(s):  
Heterocyclic Compounds ◽  
Nitrogen Heterocycles ◽  
Reaction Conditions ◽  
Cascade Cyclization ◽  
Radical Cascade ◽  
Nitrogen Heterocyclic

An iron-catalyzed radical cascade cyclization of dienes initiated by an alkoxycarbonyl radical has been developed in the presence of (NH4)2S2O8, leading to a series of fused nitrogen heterocyclic compounds under relatively mild reaction conditions.

Palladium-Catalyzed C–P Cross-Coupling between (Het)aryl Halides and Secondary Phosphine Oxides

Synthesis ◽  
2019 ◽  
Vol 51 (11) ◽  
pp. 2379-2386 ◽  
Author(s):  
Gladis Zakirova ◽  
Dmitrii Mladentsev ◽  
Nataliya Borisova
Keyword(s):  
Electronic Properties ◽  
Heterocyclic Compounds ◽  
Cross Coupling ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Tertiary Phosphine ◽  
Reaction Conditions ◽  
Efficient Procedure ◽  
Palladium Catalyzed ◽  
Tertiary Alkyl

An efficient procedure for C–P bond formation via the palladium-catalyzed [Pd(OAc)2/dppf/Cs2CO3] reaction between dichloroheterocycles and secondary phosphine oxides was developed. The steric and electronic properties of substituents were varied to establish the scope and limitations of the method developed. By applying these conditions, a variety of new heterocyclic compounds bearing two tertiary phosphine oxides were successfully synthesized in moderate to excellent yields. After adjustments to the reaction conditions [Pd(OAc)2/dippf/t-BuOK], cross-coupling of secondary phosphine oxides with bulky (secondary or tertiary alkyl) substituents on the phosphorus atom was achieved. Extension of the methodology to monohalohetarenes and monohaloarenes was successfully carried out; once again, the steric and electronic properties of the halides were varied widely. The desired reaction occurred in all cases studied, giving high to excellent yields of product regardless of the nature and positions of substituents.

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