The reported methodologies for the synthesis of chromane derivatives through the reaction of salicylaldehyde and enolates are discussed. The enolates and their equivalents involved in the reactions discussed in this article were derived from ketones, nitroalkanes, malononitrile and α,β-unsaturated compounds.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3554813PMC
http://dx.doi.org/10.3762/bjoc.8.244DOI Listing

Publication Analysis

Top Keywords

salicylaldehyde enolates
8
enolates equivalents
8
chromane derivatives
8
reactions salicylaldehyde
4
equivalents versatile
4
versatile synthetic
4
synthetic routes
4
routes chromane
4
derivatives reported
4
reported methodologies
4

Similar Publications

The diorganotin(IV) complexes (5-20) were synthesized in the present research from 4-fluorophenoxyacetic hydrazide and salicylaldehyde derivatives-based hydrazone ligands (1-4) to get an effective biological agent to combat microbial and oxidant deformities. Numerous spectral techniques such as (H, C, Sn) NMR, UV-Vis, IR, and mass spectrometry were executed to illuminate the composition of complexes. These techniques ascertained tridentate chelation of hydrazone ligands with tin metal through enolic, phenolic oxygens and imine nitrogen, revealing pentacoordinated geometry of the complexes.

View Article and Find Full Text PDF

Enantioselective synthesis of 4-amino-3,4-dihydrocoumarins and their non-cyclic hydroxyester precursors: Biological evaluation for the treatment of glioblastoma multiforme.

Eur J Med Chem

December 2022

Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad de Sevilla, C/ Profesor García González, 2, 41012, Sevilla, Spain.

The stereoselective addition of ethyl acetate enolate to the C═N bond of N-tert-butylsulfinylimines has been investigated in depth. A significant effect of the LHMDS amount and the N-sulfinylimine nature on the stereoselectivity of the process was observed. Conditions were found where sulfinylimines of differently substituted salicylaldehydes derivatives, ethyl acetate, and LHMDS afforded the corresponding addition products as a single diastereomer in good yields.

View Article and Find Full Text PDF

Reductive annulations of arylidene malonates with unsaturated electrophiles using photoredox/Lewis acid cooperative catalysis.

Chem Sci

March 2019

Department of Chemistry , Center for Molecular Innovation and Drug Discovery , Northwestern University, 2145 Sheridan Road , Evanston , Illinois 60208 , USA . Email:

A cooperative Lewis acid/photocatalytic reduction of salicylaldehyde-derived arylidene malonates provides access to a versatile, stabilized radical anion enolate. Using these unusual umpolung operators, we have developed a novel route to access densely functionalized carbo- and heterocycles through a radical annulation addition pathway.

View Article and Find Full Text PDF

Microwave-Assisted Organocatalyzed Rearrangement of Propargyl Vinyl Ethers to Salicylaldehyde Derivatives: An Experimental and Theoretical Study.

Chemistry

December 2015

Departamento de Química Biológica y Biotecnología, Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas, Avenida Astrofísico Francisco Sánchez 3, 38206 La Laguna, Tenerife (Spain).

Article Synopsis
  • The study describes a method using microwave-assisted imidazole to transform propargyl vinyl ethers into various salicylaldehydes.
  • The reaction is simple, scalable, and can handle different substitutions on the starting material, producing a range of complex structures.
  • Notably, this method successfully led to the first total synthesis of morintrifolin B, and theoretical calculations match the experimental findings, supporting a complex reaction mechanism.
View Article and Find Full Text PDF

The reported methodologies for the synthesis of chromane derivatives through the reaction of salicylaldehyde and enolates are discussed. The enolates and their equivalents involved in the reactions discussed in this article were derived from ketones, nitroalkanes, malononitrile and α,β-unsaturated compounds.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!