Synthesis of Functionalized Coumarins

Authors

  • Ahmad Shaabani Department of Chemistry, Faculty of Sciences, Shahid Beheshti University, P.O. Box 19396-4716 Tehran, I.R. IRAN
  • Ali Hossein Rezayan Department of Chemistry, Faculty of Sciences, Shahid Beheshti University, P.O. Box 19396-4716 Tehran, I.R. IRAN
  • Rahim Ghadari Department of Chemistry, Faculty of Sciences, Shahid Beheshti University, P.O. Box 19396-4716 Tehran, I.R. IRAN
Abstract:

The synthesis of functionalized 2-oxo-2H-coumarin derivatives has been studied by a one-pot reaction of o-hydroxybenzaldehyde, ethyl 2-bromoacetate and triphenylphosphine in the presence of catalytic amount of triethyl amine in EtOAc, water or under solvent free conditions. We have found the best results obtained under solvent free condition.

Upgrade to premium to download articles

Sign up to access the full text

Already have an account?login

similar resources

synthesis of functionalized coumarins

the synthesis of functionalized 2-oxo-2h-coumarin derivatives has been studied by a one-pot reaction of o-hydroxybenzaldehyde, ethyl 2-bromoacetate and triphenylphosphine in the presence of catalytic amount of triethyl amine in etoac, water or under solvent free conditions. we have found the best results obtained under solvent free condition.

full text

Functionalized 4-hydroxy coumarins: novel synthesis, crystal structure and DFT calculations.

A novel short-step methodology for the synthesis in good yields of functionalized coumarins has been developed starting from an activated precursor, the N-hydroxysuccinimide ester of O-acetylsalicylic acid. The procedure is based on a tandem C-acylation-cyclization process under mild reaction conditions. The structure of 3-methoxycarbonyl-4-hydroxy coumarin has been established by X-ray diffrac...

full text

A facile transformation of amino acids to functionalized coumarins.

The synthesis of novel chiral coumarins functionalized with proteinogenic amino acid side chains via N-protected γ-amino-β-keto esters and their incorporation into the cell permeable HIV-1 TAT peptide through the modified solid phase peptide synthesis are described.

full text

Total synthesis of six 3,4-unsubstituted coumarins.

In this article we describe a new methodology for the total synthesis of 3,4-unsubstituted coumarins from commercially available starting materials. Six examples were prepared, including five naturally occurring coumarins--7-hydroxy-6,8-dimethoxy-coumarin (isofraxidin), 7-hydroxy-6-methoxycoumarin (scopoletin), 6,7,8-trimethoxy-coumarin, 6,7-dimethoxycoumarin (scoparone), and 7,8-dihydroxycouma...

full text

Biological synthesis of coumarins in Escherichia coli

BACKGROUND Coumarins are a major group of plant secondary metabolites that serves as defense compounds against pathogens. Although coumarins can be obtained from diverse plant sources, the use of microorganisms to synthesize them could be an alternative way to supply building blocks for the synthesis of diverse coumarin derivatives. RESULTS Constructs harboring two genes, F6'H (encoding ferul...

full text

Synthesis of Allylic Amide Functionalized 2H-Chromenes and Coumarins Using a One-Pot Overman Rearrangement and Gold(I)-Catalyzed Hydroarylation.

A four-step synthesis of allylic trichloroacetimidates bearing a 2-proparyloxyaryl group has been developed from readily available 2-hydroxybenzaldehydes, and these have been used for the preparation of allylic amide derived 2H-chromenes using an Overman rearrangement and a 6-endo-dig hydroarylation. High yields of the 2H-chromenes were achieved using a stepwise approach involving an Overman re...

full text

My Resources

Save resource for easier access later

Save to my library Already added to my library

{@ msg_add @}


Journal title

volume 30  issue 4

pages  19- 22

publication date 2011-12-01

By following a journal you will be notified via email when a new issue of this journal is published.

Hosted on Doprax cloud platform doprax.com

copyright © 2015-2023