Next Article in Journal
A Convenient Four-Step Synthesis of 1-{β-[3-(4-Methoxy-phenyl)Propoxy]-4-Methoxyphenethyl}-1H-Imidazole Hydrochloride as a Probing Tool for SOCE Assays
Previous Article in Journal
(E)-3-Methyl-6-(3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-en-1-yl)-2(3H)-benzothiazolone
Article Menu

Export Article

Open AccessCommunication
Molbank 2016, 2016(4), M908; doi:10.3390/M908

Straightforward Synthesis of 2(5H)-Furanones as Promising Cross-Coupling Partners: Direct Furanone Annulation Utilizing Ti-Mediated Aldol Addition

Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan
*
Authors to whom correspondence should be addressed.
Academic Editor: Norbert Haider
Received: 31 July 2016 / Revised: 19 September 2016 / Accepted: 19 September 2016 / Published: 22 September 2016
View Full-Text   |   Download PDF [1686 KB, uploaded 22 September 2016]   |  

Abstract

Direct 2(5H)-furanone annulation produces promising cross-coupling partners incorporating m- or p-bromo- and p-tosyloxyphenyl groups into the 5-position of a notable 2(5H)-furanone pharmacore. The present one-pot annulation method involves two distinctive reactions: (i) a powerful and crossed Ti-direct aldol addition and (ii) an acid-induced characteristic cyclo-condensation, leading to 2(5H)-furanones. Suzuki-Miyaura cross-coupling of 5-(4-bromophenyl)-furan-2(5H)-ones, 5-(4-tosyloxyphenyl)-3,4-dimethylfuran-2(5H)-ones and a furan derivative successfully afforded the corresponding products with the 2(5H)-furanone skeleton. View Full-Text
Keywords: Cross-aldol reaction; titanium chloride; furanone; furanone annulation; Ti-mediated reaction; 1,1-dimethoxyacetone; bromophenyl ketone; tosyloxy ketone; cross-coupling partner; Suzuki-Miyaura cross-coupling Cross-aldol reaction; titanium chloride; furanone; furanone annulation; Ti-mediated reaction; 1,1-dimethoxyacetone; bromophenyl ketone; tosyloxy ketone; cross-coupling partner; Suzuki-Miyaura cross-coupling
Figures

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary materials

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Ban, Y.; Ashida, Y.; Nakatsuji, H.; Tanabe, Y. Straightforward Synthesis of 2(5H)-Furanones as Promising Cross-Coupling Partners: Direct Furanone Annulation Utilizing Ti-Mediated Aldol Addition. Molbank 2016, 2016, M908.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molbank EISSN 1422-8599 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top