Synthesis of substituted naphthofurans has been achieved via an efficient cascade Rh(ii)/Yb(iii) catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with β-naphthols.
We have synthesized and characterized a variety of fat-soluble, low-melting and medicinally useful 4-aryl-4H-chromenes from H-cardanol (side-chain perhydrogenated cardanol, 3-pentadecylphenol), a renewable and low-cost product from locally grown cashew nut trees (Anacardium occidentale L.). We incorporated H-cardanol into the aromatic rings of either 4H-chromene or phenol, or both. Substitution of C4SMe in N-methyl-4-(methylthio)-3-nitro-4Hchromene-2-amines with H-cardanol was regio-specific at the C6 position.
The synthesis and gelation properties of a structurally simple, renewable-resource-based glucose-triazolehydrogenated cardanol conjugate (GTHCC) are reported. The conjugation of hydrogenated cardanol and glucose was done using a triazole linker employing copper(I) mediated acetylene azide cycloaddition 'click' chemistry in the key step. The GTHCC was found to form four different classes of gels; namely, (i) hydrogel from aqueous-protic solvents, (ii) organogel from non-polar solvents, (iii) gel from vegetable oil and (iv) gel from petroleum oil. In a water-methanol (1 : 1) mixture, the conjugate acted as a stable thermoreversible supergelator, even at a very low gelator concentration of 0.03% w/v. Unlike glycosidebased gels derived from hydrogenated cardanol and glucose, the GTHCC is stable under acidic as well as basic conditions, owing to the covalent linkages in the tether. The intrinsic fluorescence of the hydrogel was found to be sensitive towards a gel-sol transition.
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