60249-17-4Relevant academic research and scientific papers
Silica gel enables Achmatowicz rearrangement with KBr/oxone under “anhydrous” condition for one-pot functionalization
Zhao, Guodong,Tong, Rongbiao
, p. 1669 - 1675 (2019/01/04)
Silica gel was found to effectively promote Achmatowicz rearrangement (AchR) using KBr/oxone under near anhydrous condition. This new protocol allows direct functionalization of AchR products in a one-pot manner, effectively reducing the cost, time, and e
Expeditious metal-free access to functionalized polycyclic acetals under mild aqueous conditions
Kasare, Sanghratna,Bankar, Siddheshwar K.,Ramasastry
, p. 4284 - 4287 (2014/11/08)
A facile approach for the synthesis of furopyrans and bicyclic bisacetals under mild aqueous conditions is described. This potentially green, diversity oriented approach involves cascade Michael addition and cycloacetalization of pyranones and 1,3-dicarbo
Synthesis, physicochemical characterization, and biological evaluation of 2-(1'-hydroxyalkyl-3-hydroxypyridin-4-ones: Novel iron chelators with enhanced pFe3+ values
Liu, Zu D.,Khodr, Hicham H.,Liu, Ding Y.,Lu, Shu L.,Hider, Robert C.
, p. 4814 - 4823 (2007/10/03)
The synthesis of a range of 2-(1'-hydroxyalkyl)-3-hydroxypyridin-4-ones as bidentate iron(III) chelators with potential for oral administration is described. The pK(a) values of the ligands and the stability constants of their iron(III) complexes have been determined. Results indicate that the introduction of a 1'-hydroxyalkyl group at the 2-position leads to a significant improvement in the pFe3+ values. Such an effect was found to be greater with the hydroxyethyl substituent than with the hydroxy-methyl substituent, particularly in the cases of 1-ethyl-2(1'-hydroxyethyl)-3- hydroxypyridin-4-one (pFe3+ = 21.4) and 1,6-dimethyl-2-(1'-hydroxyethyl)3- hydroxypyridin-4-one (pFe3+ = 21.5) where an enhancement on pFe3+ values in the region of two orders of magnitude is observed, as compared with Deferiprone (1,2-dimethyl-3-hydroxypyridin-4-one) (pFe3+ = 19.4). The ability of these novel 3-hydroxypyridin-4-ones to facilitate the iron excretion in bile was investigated using a [59Fe] ferritin-loaded rat model. Chelators and prodrug chelators possessing high pFe3+ values show great promise in their ability to remove iron under in vivo conditions.
Regioselectivity in the palladium-catalyzed addition of carbon nucleophiles to dihydropyran derivatives
Brescia, Marc-Raleigh,Shimshock, Yvonne Class,DeShong, Philip
, p. 1257 - 1263 (2007/10/03)
The regioselectivity of Pd-catalyzed malonate or sulfonylacetate addition to dihydropyran derivatives is highly dependent upon the substitution pattern of the dihydropyran nucleus and is governed by electronic, rather than steric factors. In certain instances, subtle steric features also play a role in controlling regioselectivity by altering the conformation of the intermediate η3-allyl Pd-complex.
IMPROVED PROCEDURE FOR THE SYNTHESIS OF 6-ALKOXY-2,3-DIHYDRO-6H-PYRAN-3-ONES (2,3-DIDEOXY-DL-PENT-2-ENOPYRANOS-4-ULOSES). NEAT CONVERSION INTO POLYFUNCTIONALIZED CYCLOPENTENONES.
Mucha, Bernd,Hoffmann, H.Martin R.
, p. 4489 - 4492 (2007/10/02)
The glycosidic bond of 6-alkoxy-2,3-dihydro-6H-pyran-3-ones (3) is made advantageously in the presence of catalytic ZnCl2*etherate.A palladium-assisted transformation of 3 affords trans-4-alkoxy-5-hydroxy-2-cyclopenten-1-ones (4) in good yield.
