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.

Regioselective N-alkylation of (2-chloroquinolin-3-yl) methanol with N-heterocyclic compounds using the Mitsunobu reagent

2011 ◽  
Vol 65 (3) ◽  
Author(s):  
Selvaraj Roopan ◽  
Fazlur-Rahman Khan ◽  
Jong Jin
Keyword(s):  
Natural Product ◽  
Organic Synthesis ◽  
Heterocyclic Compounds ◽  
Building Blocks ◽  
Natural Product Synthesis ◽  
Mitsunobu Reaction ◽  
Reaction Conditions ◽  
Diethyl Azodicarboxylate ◽  
Nitrogen Heterocyclic

AbstractThe Mitsunobu reaction is a well-established fundamental reaction and has been widely applied in organic synthesis. In this paper, under Mitsunobu conditions dehydration proceeds between (2-chloroquinolin-3-yl)methanol and nitrogen heterocyclic compounds such as quinazolinone, pyrimidone, 2-oxoquinoline in dry THF in the presence of triethylamine, triphenylphosphane and diethyl azodicarboxylate to give the corresponding products. As part of our recent research, we attempted to couple two N-heterocyclic compounds under Mitsunobu reaction conditions to provide efficient building blocks for natural product synthesis.

Heterocyclic compounds from alloxan and amines. X. Amine purpurates

1970 ◽  
Vol 23 (2) ◽  
pp. 323 ◽  
Author(s):  
JW Clark-Lewis ◽  
K Moody
Keyword(s):  
Carbon Dioxide ◽  
Acetic Acid ◽  
Nitrogen Atom ◽  
Heterocyclic Compounds ◽  
Nitrogen Heterocycles ◽  
Heterocyclic Amine ◽  
Reaction Conditions

Secondary and tertiary alicyclic amines (piperidine, morpholine, N-ethyl-piperidine, and N-methylmorpholine), and aromatic nitrogen heterocycles (benzimidazole, 2-methyl- and 2-t-butyl-benzimidazole, and pyridine), are shown to yield the heterocyclic amine purpurates (murexide analogues) by reaction with anhydrous alloxan in dry acetic acid. The central nitrogen atom of the purpurate anion, normally derived from ammonia, is considered to arise from degradation of some of the alloxan, and is accompanied by liberation of carbon dioxide. Pyrrolidine did not yield a purpurate (or carbon dioxide) under the reaction conditions.

scholarly journals From Alkynes to Heterocycles through Metal-Promoted Silylformylation and Silylcarbocyclization Reactions

Catalysts ◽  
2020 ◽  
Vol 10 (9) ◽  
pp. 1012 ◽  
Author(s):  
Gianluigi Albano ◽  
Laura Antonella Aronica
Keyword(s):  
Detailed Analysis ◽  
Heterocyclic Compounds ◽  
Functional Group ◽  
Biologically Active ◽  
Reaction Conditions ◽  
Synthetic Compounds ◽  
Heterocyclic Derivatives ◽  
Nitrogen Heterocyclic ◽  
Natural And Synthetic

Oxygen and nitrogen heterocyclic systems are present in a large number of natural and synthetic compounds. In particular, oxa- and aza-silacyclane, tetrahydrofuran, benzofuran, cycloheptadifuranone, cycloheptadipyrrolone, pyrrolidine, lactone, lactam, phthalan, isochromanone, tetrahydroisoquinolinone, benzoindolizidinone, indoline and indolizidine scaffolds are present in many classes of biologically active molecules. Most of these contain a C=O moiety which can be easily introduced using carbonylative reaction conditions. In this field, intramolecular silylformylation and silylcarbocyclization reactions may afford heterocyclic compounds containing a carbonyl functional group together with a vinylsilane moiety which can be further transformed. Considering these two aspects, in this review a detailed analysis of the literature data regarding the application of silylformylation and silylcarbocyclization reactions to the synthesis of several heterocyclic derivatives is reported.

Fe-Catalyzed Conjunctive Cross-Couplings of Unactivated Alkenes with Grignard Reagents

2020 ◽  
Author(s):  
Lei Liu ◽  
Wes Lee ◽  
Cassandra R. Youshaw ◽  
Mingbin Yuan ◽  
Michael B. Geherty ◽  
...  
Keyword(s):  
Functional Groups ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Turnover Frequency ◽  
Diverse Range ◽  
Cascade Cyclization ◽  
Radical Cascade

The first iron-catalyzed three-component cross-coupling of unactivated olefins with alkyl halides and Grignard reagents is reported. The reaction operates under fast turnover frequency and tolerates a diverse range of sp2-hybridized nucleophiles, alkyl halides, and unactivated olefins bearing diverse functional groups to yield the desired 1,2-alkylarylated products with high regiocontrol. Further, we demonstrate that this protocol is amenable for the synthesis of new (hetero)carbocycles including tetrahydrofurans and pyrrolidines via a three-component radical cascade cyclization/arylation that forges three new C-C bonds.

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.

Phenothiazine and amide-ornamented novel nitrogen heterocyclic hybrids: synthesis, biological and molecular docking studies

2020 ◽  
Vol 44 (10) ◽  
pp. 4049-4060
Author(s):  
Ramar Sivaramakarthikeyan ◽  
Ayyanar Karuppasamy ◽  
Shunmugam Iniyaval ◽  
Krishnaraj Padmavathy ◽  
Wei-Meng Lim ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Nitrogen Heterocycles ◽  
Docking Studies ◽  
Spectral Techniques ◽  
Molecular Docking Studies ◽  
Nitrogen Heterocyclic

The synthesis of phenothiazine and amide-ornamented nitrogen heterocycles (25–34) has been accomplished utilizing a multi-step synthetic protocol and the structures have been established based on physical and spectral techniques.

Eosin Y photoredox catalyzed net redox neutral reaction for regiospecific annulation to 3-sulfonylindoles via anion oxidation of sodium sulfinate salts

2018 ◽  
Vol 16 (4) ◽  
pp. 536-540 ◽  
Author(s):  
Rajendra S. Rohokale ◽  
Shrikant D. Tambe ◽  
Umesh A. Kshirsagar
Keyword(s):  
Visible Light ◽  
Eosin Y ◽  
Cascade Cyclization ◽  
Neutral Reaction ◽  
Neutral Process ◽  
Radical Cascade

An eosin Y photoredox catalyzed net redox neutral process for 3-sulfonylindoles via the anionic oxidation of sodium sulfinate salts and its radical cascade cyclization with 2-alkynyl-azidoarenes was developed with visible light as a mediator.

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