An efficient synthesis of flavans from salicylaldehyde and acetophenone derivatives

An efficient total synthesis of flavans from the reactions of salicylaldehyde and acetophenone derivatives is reported. The synthesis involves preparation of chalcones through an aldol reaction followed by reduction of both the double bond and the ketone using NaBH 4 and an acetic acid mediated cycl...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2011-12, Vol.52 (50), p.6716-6718
Main Authors: Mazimba, Ofentse, Masesane, Ishmael B., Majinda, Runner R.
Format: Article
Language:English
Subjects:
Acetic acid
Acetophenone
Aldol condensation
Aromatic compounds
Bonding
Chemistry
Derivatives
Exact sciences and technology
Flavan
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Ketones
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Reduction
Salicylaldehyde
Synthesis (chemistry)
Tetrahedrons
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An efficient total synthesis of flavans from the reactions of salicylaldehyde and acetophenone derivatives is reported. The synthesis involves preparation of chalcones through an aldol reaction followed by reduction of both the double bond and the ketone using NaBH 4 and an acetic acid mediated cyclization. Methoxy groups on the aromatic rings did not affect significantly the yields of the procedure.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.09.147