Phenanthrenequinone

Wendland, R.T.; LaLonde, John

doi:10.1002/0471264180.os034.26

Organic Syntheses 2003

DOI: 10.1002/0471264180.os034.26

|View full text |Cite

Phenanthrenequinone

R.T. Wendland

John LaLonde

Abstract: Phenanthrenequinone reactant: 100 g. (0.56 mole) of phenanthrene byproduct: anthraquinone product: phenanthrenequinone

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2016

2023

Publication Types

Select...

Article2

Relationship

Self Cite0

Independent2

Authors

Journals

Cited by 2 publications

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Catalysis of Heterocyclic Azadiene Cycloaddition Reactions by Solvent Hydrogen Bonding: Concise Total Synthesis of Methoxatin

Glinkerman

Boger

2016

J. Am. Chem. Soc.

View full text Add to dashboard Cite

Although examined for decades, no general approach to catalysis of the inverse electron demand Diels–Alder reactions of heterocyclic azadienes has been introduced. Typically, additives such as Lewis acids lead to non-productive consumption of the electron-rich dienophiles without productive activation of the electron-deficient heterocyclic azadienes. Herein, we report the first general method for catalysis of such cycloaddition reactions by using solvent hydrogen bonding of non-nucleophilic perfluoroalcohols, including hexafluoroisopropanol (HFIP) and trifluoroethanol (TFE), to activate the electron-deficient heterocyclic azadienes. Its use in promoting the cycloaddition of 1,2,3-triazine 4 with enamine 3 as the key step of a concise total synthesis of methoxatin is described.

show abstract

Catalysis of Heterocyclic Azadiene Cycloaddition Reactions by Solvent Hydrogen Bonding: Concise Total Synthesis of Methoxatin

Glinkerman

Boger

2016

J. Am. Chem. Soc.

View full text Add to dashboard Cite

show abstract

Revisiting the coupling reaction between 4-aminoantipyrine and phenols: a potential one-pot reaction pathway to 4,11- and 5,12-naphthoxazepine isomers

Otim

2023

Can. J. Chem.

View full text Add to dashboard Cite

This journal (Canadian Journal of Chemistry) published a while ago a set of seminal studies revealing the underlying mechanisms supporting the then widely used analytical technique for detecting phenols at low levels in domestic water supply using 4-aminoantipyrine (4-AAP). The current paper revisits these studies with a primary focus on the dimension of this reaction that synthesizes 6- and 7-membered heterocyclic rings containing both N and O in a single step. Here we report a rather unusual outcome of the reaction in which, while the oxidative coupling of 4-AAP to 1-naphthol in aqueous solution at high p<i>H</i> (or condensation with 1,4-naphthoquinone in chloroform) leads to the same naphthoquinonimide product, a similar set of reactions with 2-naphthol and 1,2-naphthoquinone produces two isomeric forms of an oxazepine instead. In one isomer, the 4-AAP/naphthol C-N and the C-O linkages are at positions 1 and 2 of naphthyl ring, respectively and in the other form, these linkages are at positions 2 and 1, respectively. This unexpected difference in a one-pot reaction at ambient temperature is potentially the flexibility needed to synthesize families of pharmaceutically relevant oxazepines. Spectroscopic features useful for identifying 12 heterocyclic compounds, nine of which are new, are also provided.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Phenanthrenequinone

Abstract: Phenanthrenequinone reactant: 100 g. (0.56 mole) of phenanthrene byproduct: anthraquinone product: phenanthrenequinone

Cited by 2 publications

References 7 publications

Catalysis of Heterocyclic Azadiene Cycloaddition Reactions by Solvent Hydrogen Bonding: Concise Total Synthesis of Methoxatin

Catalysis of Heterocyclic Azadiene Cycloaddition Reactions by Solvent Hydrogen Bonding: Concise Total Synthesis of Methoxatin

Revisiting the coupling reaction between 4-aminoantipyrine and phenols: a potential one-pot reaction pathway to 4,11- and 5,12-naphthoxazepine isomers

Contact Info

Product

Resources

About