2(3H)-Furanones and related substrates: Synthetic strategies and selectivity profile in their reactivity

Dyuthi/Manakin Repository

2(3H)-Furanones and related substrates: Synthetic strategies and selectivity profile in their reactivity

Show simple item record

dc.contributor.author Roshini K, Thumpakara
dc.contributor.author Dr.Prathapan, S
dc.date.accessioned 2012-06-11T08:43:55Z
dc.date.available 2012-06-11T08:43:55Z
dc.date.issued 2007-11
dc.identifier.uri http://dyuthi.cusat.ac.in/purl/2915
dc.description Department of Applied Chemistry, Cochin University of Science and Technology en_US
dc.description.abstract The synthesis and reactions of simple derivatives of 2(3H)- and 3(2H)furanones have attracted considerable attention in recent years, primarily in connection with development of routes to antitumor agents that contain this ring as central structural unit. They also serve as useful synthetic building blocks for lactones and furans and are the precursors of a wide variety of biologically important heterocyclic systems. Although a number of syntheses of furanones were known they were in many cases limited to specific substitution pattems. The development of altemative strategies for the preparation of these heterocycles is therefore of considerable importance or continues to be a challenge.We propose to develop new and general approaches to the synthesis of furanone ring systems from simple and readily available starting materials since we were interested in examining their rich photochemistry. The photochemical reactivity of Beta,gama-unsaturated lactams and lactones is a subject of current interest. Some of the prominent photoreaction pathways of unsaturated lactones include decarbonylation, solvent addition to double bonds, decarboxylation, migration of aryl substituents and dimerisation. lt was reported earlier that the critical requirement for clean photochemical cleavage of the acyl-oxygen bond is the presence ofa double bond adjacent to the ether oxygen and 2(3H)-furanones possessing this structural requirement undergo facile decarbonylation. But related phenanthrofuranones are isolated as photostable end products upon irradiation. Hence we propose to synthesis a few phenanthro-2(3H)-furanones to study the effect of a radical stabilising group at 3-position of furanone ring on photolysis. To explore the tripletmediated transformations of 2(3H)-furanones in polar and nonpolar solvents a few 3,3-bis(4-chlorophenyl)-5-aryl-3H-furan-2-ones and 3,3-di(p-tolyl)-5-aryl- 3H-furan-2-ones were synthesised from the corresponding dibenzoylstyrene precursors by neat thermolysis. Our aim was to study the nature of intermediates involved in these transformations.We also explored the possibility of developing a new and general approach to the synthesis of 3(2H)-furanones from simple and readily available starting materials since such general procedures are not available. The protocol developed by us employs readily available phenanthrenequinone and various 4-substituted acetophenones as starting materials and provides easy access to the required 3(2H)-furanone targets. These furanone derivatives have immense potential for further investigations .We also aimed the synthesis of a few dibenzoylalkene-type systems such as acenaphthenone-2—ylidene ketones and phenanthrenone-9-ylidene ketones. These systems were expected to undergo thermal rearrangement to give furanones and spirofuranones. Also these systems can be categorised as quinonemethides which are valuable synthetic intermediates. en_US
dc.language.iso en en_US
dc.publisher Cochin University of Science & Technology en_US
dc.subject Furanones en_US
dc.subject Photochemistry en_US
dc.subject Chemistry en_US
dc.title 2(3H)-Furanones and related substrates: Synthetic strategies and selectivity profile in their reactivity en_US
dc.type Thesis en_US


Files in this item

Files Size Format View Description
Dyuthi-T0906.pdf 3.799Mb PDF View/Open PDF

This item appears in the following Collection(s)

Show simple item record

Search Dyuthi


Advanced Search

Browse

My Account