Please use this identifier to cite or link to this item: http://hdl.handle.net/10603/125699
Title: REARRANGEMENT OF SUBSTITUTED ARYLOXYMETHYL CHROMONES AND MECHANISTIC INVESTIGATION SYNTHYSIS OF HYDROXYHOMOISOFLAVONES AND HOMOPTEROCARPANES
Researcher: DEVARAJAN. K
Guide(s): Dr.S. BHAGAVATHY
University: B S Abdur Rahman University
Completed Date: 17.11.2016
Abstract: The aromatic Claisen rearrangement has emerged as a very important newlinetool for stereoselective C-C bond formation. Many natural products and newlineheterocyclic compounds have been synthesized using chromones and newlinechromanones by applying variants of this rearrangement as a key step. So newlinefar, there are no reports on Claisen rearrangement involving the double bond newlineof the chromone ring as part of the allyl moiety. With these facts in mind, newlinechromone-3-ylmethyl aryl ethers and chromone-2-ylmethyl aryl ethers were newlinesynthesized and the rearrangement behavior under thermal and TFA newlineconditions has been studied. newlineNovel and serendipitous finding on the synthesis of 3,3-bis-(4-oxochromen- newline3-ylmethyl)-chroman-4-one (trimeric chromone), which was newlineencountered during the synthesis of chromone-3-ylmethyl aryl ethers via newlineBuchwald-Hartwig coupling of 3-hydroxymethylchromone with bromobenzene, newlineis described. newlineThe center core of this thesis deals with the Claisen rearrangement of newlinechromone-3-ylmethyl aryl ethers. Chromone-3-ylmethyl aryl ethers with one or newlineboth vacant ortho positions have been found to undergo a novel domino [1,3]- newline[1,3]-rearrangement to give 4 -hydroxyhomoisoflavones under thermal newlineconditions while the para-substituted ethers led to 2 -hydroxyhomoisoflavones newlineinvolving a O- to C-[1,3]-migration, instead of the expected Claisen newlinerearrangement. Whereas under TFA condition, chromone-3-ylmethyl aryl newlineethers have been found to undergo a facile ortho selective [1,3]-migration at newlinethe aryl moiety to give 2and#1048973;-hydroxyhomoisoflavones. newlineHomopterocarpanes, a non-natural product which are homolog to the newlinesecond largest natural products pterocarpanes have been synthesised using newlinethe 2 -hydroxyhomoisoflavones obtained from the TFA catalysed [1,3]- newlinerearrangement of chromene-3-ylmethyl aryl ethers.The synthesis of hitherto newlineunknown trans-homopterocarpanes has been disclosed for the first time by newlineBuchwald reaction of trans-3-(2-bromobenzy)-4-chromanols. newline
Pagination: 
URI: http://hdl.handle.net/10603/125699
Appears in Departments:Department of Chemistry

Files in This Item:
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10 list of schemes.pdfAttached File8.23 MBAdobe PDFView/Open
11 list of abbeviations.pdf8.22 MBAdobe PDFView/Open
12 chapter-1.pdf8.22 MBAdobe PDFView/Open
13 chapter-2.pdf8.23 MBAdobe PDFView/Open
14 chapter-3.pdf8.23 MBAdobe PDFView/Open
15 chapter-4.pdf8.22 MBAdobe PDFView/Open
16chapter 5.pdf1.31 MBAdobe PDFView/Open
17 chapter-6.pdf8.23 MBAdobe PDFView/Open
18 summery and conclusion.pdf8.24 MBAdobe PDFView/Open
19scope for future work.pdf8.24 MBAdobe PDFView/Open
20 references.pdf8.24 MBAdobe PDFView/Open
7 table of contents.pdf8.25 MBAdobe PDFView/Open
8 list of tables.pdf8.23 MBAdobe PDFView/Open
9 list of figures.pdf8.23 MBAdobe PDFView/Open


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