Designing Substituted Furan and Pyran Derivatives from Cyclic and Acyclic Precursors: Synthesis and Applications
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
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| Title |
Designing Substituted Furan and Pyran Derivatives from Cyclic and Acyclic Precursors: Synthesis and Applications
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| Creator |
Mal, Kanchan
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| Subject |
Chemistry
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| Description |
focuses on the gold(III)-catalyzed efficient general route to densely substituted chiral 3-formyl furans under extremely mild conditions from suitably protected 5-(1-alkynyl)-2,3-dihydropyran-4-one using H2O as a nucleophile. The reaction proceeds through the initial formation of an activated alkyne–gold(III) complex intermediate, followed by either a domino nucleophilic attack/anti-endo-dig
cyclization, or the formation of a cyclic oxonium ion with subsequent attack by H2O. To confirm the proposed mechanistic pathway, we employed MeOH as a nucleophile instead of H2O to result in a substituted furo[3,2-c]pyran derivative, as anticipated. The similar furo[3,2-c]pyran skeleton with a hybrid carbohydrate–furan derivative has also been achieved through pyridinium dichromate (PDC)
oxidation of a substituted chiral 3-formyl furan. The corresponding protected 5-(1-alkynyl)-2,3-
dihydropyran-4-one can be synthesized from the monosaccharides (both hexoses and pentose) following
oxidation, iodination, and Sonogashira coupling sequences. Furthermore, to demonstrate the potentiality
of chiral 3-formyl furan derivatives, a TiBr4-catalyzed reaction of these derivatives has been shown to
offer efficient access to 1,5-dicarbonyl compounds, which on treatment with NH4OAc in slightly acidic
conditions afforded substituted furo[3,2-c]pyridine.
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| Date |
2016
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| Type |
Thesis
NonPeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://www.eprints.iicb.res.in/2670/1/Kanchan_Mal__Thesis.pdf
Mal, Kanchan (2016) Designing Substituted Furan and Pyran Derivatives from Cyclic and Acyclic Precursors: Synthesis and Applications. PhD thesis, C U. |
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| Relation |
http://www.eprints.iicb.res.in/2670/
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