Saturated oxygen and nitrogen heterocycles via oxidative coupling of alkyltrifluoroborates with alkenols, alkenoic acids and protected alkenylamines

The oxidative coupling of alkyltrifluoroborates with heteroatom-tethered vinylarenes leads to a broad range of saturated oxygen and nitrogen heterocycles.

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Methanol as a Formylating Agent in Nitrogen Heterocycles

Organic & Biomolecular Chemistry ◽

10.1039/d1ob01807h ◽

2021 ◽

Author(s):

Zhengbao Xu ◽

Lizhi Zhang

Keyword(s):

Oxidative Coupling ◽

Nitrogen Heterocycles ◽

Coupling Process

A radical mediated C-H direct formylation of N-heteroarenes with methanol is reported. The reaction features a novel iron-catalyzed Minisci oxidative coupling process using commercially available methanol as a formylated reagent....

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Palladium-Catalyzed Aerobic Oxidative Coupling of Allylic Alcohols with Anilines in the Synthesis of Nitrogen Heterocycles

The Journal of Organic Chemistry ◽

10.1021/acs.joc.8b00287 ◽

2018 ◽

Vol 83 (7) ◽

pp. 3941-3951 ◽

Cited By ~ 15

Author(s):

Gangam Srikanth Kumar ◽

Diksha Singh ◽

Manish Kumar ◽

Manmohan Kapur

Keyword(s):

Oxidative Coupling ◽

Nitrogen Heterocycles ◽

Allylic Alcohols ◽

Palladium Catalyzed

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Elemental Sulfur as Reaction Medium for the Synthesis of Fused Nitrogen Heterocycles by Oxidative Coupling between Cycloalkanones and Nitrogen Nucleophiles

Advanced Synthesis & Catalysis ◽

10.1002/adsc.201700919 ◽

2017 ◽

Vol 359 (21) ◽

pp. 3843-3847 ◽

Cited By ~ 19

Author(s):

Thanh Binh Nguyen ◽

Pascal Retailleau

Keyword(s):

Oxidative Coupling ◽

Elemental Sulfur ◽

Nitrogen Heterocycles ◽

Reaction Medium ◽

Nitrogen Nucleophiles

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Potassium Periodate Mediated Oxidative Cyclodesulfurization toward Benzofused Nitrogen Heterocycles

Synthesis ◽

10.1055/s-0039-1690855 ◽

2020 ◽

Vol 52 (13) ◽

pp. 1981-1990

Author(s):

Mookda Pattarawarapan ◽

Chuthamat Duangkamol ◽

Wong Phakhodee

Keyword(s):

Intramolecular Cyclization ◽

Oxidative Coupling ◽

Nitrogen Heterocycles ◽

Coupling Reactions ◽

Substituted Anilines ◽

Potassium Periodate ◽

High Yields ◽

Quinazolinone Derivatives ◽

Oxidative Coupling Reactions

A convenient oxidative cyclodesulfurization method toward the synthesis of benzofused nitrogen heterocycles using inexpensive and readily available potassium periodate as an oxidant was developed. Upon treating isothiocyanates with ortho-substituted anilines bearing N,N-, N,O-, and N,S-bis-nucleophiles, followed by an intramolecular cyclization of the in situ generated monothioureas, substituted 2-aminobenzazole series were rapidly accessible in good to excellent yields. The protocol can accommodate various substituents on both substrates while allowing more efficient, greener, and operational simpler process relative to other oxidative coupling reactions. Tetracyclic quinazolinone derivatives were also afforded in high yields in a single preparative step and chromatography-free.

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Hydrogen Cyanide Polymers from the Impact of Comet P/Shoemaker-Levy 9 on Jupiter

International Astronomical Union Colloquium ◽

10.1017/s025292110001469x ◽

1997 ◽

Vol 161 ◽

pp. 179-187

Author(s):

Clifford N. Matthews ◽

Rose A. Pesce-Rodriguez ◽

Shirley A. Liebman

Keyword(s):

Amino Acids ◽

Solar System ◽

Hydrogen Cyanide ◽

Nitrogen Heterocycles ◽

Laboratory Studies ◽

Heterogeneous Solids ◽

The Many ◽

Comet Halley ◽

The Impact ◽

By Products

AbstractHydrogen cyanide polymers – heterogeneous solids ranging in color from yellow to orange to brown to black – may be among the organic macromolecules most readily formed within the Solar System. The non-volatile black crust of comet Halley, for example, as well as the extensive orangebrown streaks in the atmosphere of Jupiter, might consist largely of such polymers synthesized from HCN formed by photolysis of methane and ammonia, the color observed depending on the concentration of HCN involved. Laboratory studies of these ubiquitous compounds point to the presence of polyamidine structures synthesized directly from hydrogen cyanide. These would be converted by water to polypeptides which can be further hydrolyzed to α-amino acids. Black polymers and multimers with conjugated ladder structures derived from HCN could also be formed and might well be the source of the many nitrogen heterocycles, adenine included, observed after pyrolysis. The dark brown color arising from the impacts of comet P/Shoemaker-Levy 9 on Jupiter might therefore be mainly caused by the presence of HCN polymers, whether originally present, deposited by the impactor or synthesized directly from HCN. Spectroscopic detection of these predicted macromolecules and their hydrolytic and pyrolytic by-products would strengthen significantly the hypothesis that cyanide polymerization is a preferred pathway for prebiotic and extraterrestrial chemistry.

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