Reaction between naphthols and dimethyl acetylenedicarboxylate in the presence of phosphites. Synthesis of stable oxa-2λ5-phosphaphenanthrenes, and benzochromene derivatives

Literature Information

Publication Date 2003-01-14
DOI 10.1039/B210263N
Impact Factor 3.876
Authors

Issa Yavari, Mohammad Anary-Abbasinejad, Zinatossadat Hossaini


View Original

Abstract

The reaction of dimethyl acetylenedicarboxylate (DMAD) with 2-naphthol in the presence of trimethyl or triphenyl phosphite leads to stable dimethyl oxa-2λ5-phosphaphenanthrene derivatives in good yields. The reaction of DMAD and trimethyl phosphite in the presence of 1-naphthol or 8-hydroxyquinoline leads to dimethyl 2-(dimethoxyphosphoryl)-3-(1-hydroxy-2-naphthyl)succinate or dimethyl 2-(dimethoxyphosphoryl)-3-(8-hydroxyquinolin-7-yl)succinate in excellent yields. Using triethyl phosphite and DMAD in the presence of 2-naphthol or 1-naphthol produces methyl 3-oxo-2,3-dihydro-1H-benzo[f]chromene-1-carboxylate or methyl 2-oxo-3,4-dihydro-2H-benzo[h]chromene-4-carboxylate in excellent yields.

Related Literature

Molybdenum carbide nanoparticles within carbon nanotubes as superior catalysts for γ-valerolactone production via levulinic acid hydrogenation

Estevão F. Mai, Marta A. Machado, Thomas E. Davies, Jose A. Lopez-Sanchez, Victor Teixeira da Silva

2014-07-10 Communication

DOI: 10.1039/C4GC00920G

A nickel doped perovskite catalyst for reforming methane rich biogas with minimal carbon deposition

Samuel E. Evans, John Z. Staniforth, Richard J. Darton, R. Mark Ormerod

2014-07-31 Paper

DOI: 10.1039/C4GC00782D

Fermentation of hydrolysate detoxified by pervaporation through block copolymer membranes

Douglas R. Greer, Thalita P. Basso, Ana B. Ibanez, Stefan Bauer, Jeffrey M. Skerker, A. Evren Ozcam, Dacia Leon, Chaeyoung Shin, Adam P. Arkin

2014-07-11 Paper

DOI: 10.1039/C4GC00756E

Hydrogenation of levulinic acid to γ-valerolactone by Ni and MoOx co-loaded carbon catalysts

Shota Kanno, Kenichi Kon

2014-06-05 Paper

DOI: 10.1039/C4GC00735B

Lactic acid production from glucose over polymer catalysts in aqueous alkaline solution under mild conditions

Xincheng Wang, Yanlei Song, Chongpin Huang, Fengbing Liang, Biaohua Chen

2014-06-26 Paper

DOI: 10.1039/C4GC00811A

Mesoporous carbon–silica solid acid catalysts for producing useful bio-products within the sugar-platform of biorefineries

Patrícia A. Russo, Margarida M. Antunes, Patrícia Neves, Paul V. Wiper, Enza Fazio, Fortunato Neri, Francesco Barreca, Luís Mafra, Martyn Pillinger, Nicola Pinna, Anabela A. Valente

2014-07-07 Paper

DOI: 10.1039/C4GC01037J

You might also like

Compound Q&A

How should 2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) be stored?

2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) should be stored in ...

615-45-22-Methylbenzene-1,4-...
Compound Q&A

Is (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide (CAS: 132747-20-7) safe?

(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is generally considered sa...

132747-20-7(1S,4S)-2,5-Diazabic...
Compound Q&A

What industries use (6-Chloropyridazin-3-YL)methanamine (CAS: 871826-15-2)?

(6-Chloropyridazin-3-YL)methanamine finds applications in the pharmaceutical ind...

871826-15-2(6-Chloropyridazin-3...
Compound Q&A

What are the main uses of 2-Fluoro-3-methylphenol (CAS: 77772-72-6)?

2-Fluoro-3-methylphenol is primarily used in the synthesis of pharmaceuticals, p...

77772-72-62-Fluoro-3-methylphe...
Compound Q&A

What precautions should be taken when handling 3-Methoxy-4-nitrobenzonitrile (CAS: 177476-75-4)?

When handling 3-Methoxy-4-nitrobenzonitrile, it is important to wear appropriate...

177476-75-43-Methoxy-4-nitroben...
Compound Q&A

What precautions should be taken when handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4)?

When handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4), it is ...

211949-57-4[1,3]Oxazolo[4,5-b]p...
Compound Q&A

What regulatory guidelines apply to 4-Ethynylbenzamide (CAS: 90347-86-7)?

4-Ethynylbenzamide (CAS: 90347-86-7) falls under various regulatory guidelines i...

90347-86-74-Ethynylbenzamide
Compound Q&A

What are the main uses of 3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone (CAS: 186822-57-1)?

3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone is primarily used as an intermediat...

186822-57-13-(2-Ethylphenyl)-2-...
Compound Q&A

What is (2-Fluoro-6-methoxyphenyl)acetic acid (CAS: 500912-19-6)?

(2-Fluoro-6-methoxyphenyl)acetic acid, also known as 4-fluoro-3-methoxybenzoic a...

500912-19-6(2-Fluoro-6-methoxyp...
Compound Q&A

What is the market or research trend for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9)?

Market trends for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9) indicat...

102196-18-92-[4-(Hydroxymethyl)...

Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
Articles per Year: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.