Ultrasound promoted facile synthesis of some pentafluoropyridine derivatives at ambient conditions

Abstract

Some pentafluoropyridine derivatives have been synthesized by the reaction of pentafluoropyridine with appropriate mono and bidentate nucleophile under ultrasonic irradiation. This new methodology provides good to excellent yields in short reaction times (25-120 min) at room temperature.

Novel fluorinated benzimidazole-based scaffolds and their anticancer activity in vitro

“…DEPT was used to assign environment (CH, CH 2 , CH 3 ) in 13 C NMR spectra. The solvent is specified in brackets.…”

“…Substitution patterns available by stepwise replacement of fluorines are different from those afforded by electrophilic aromatic substitution and allow preparation of diverse structural types [7,8]. Potential for ring formation with bidentate nucleophiles [9,10], control of regiochemistry through hard/soft nucleophilic interactions [11, 12,], and alternative methods for promoting reaction by ultrasound [13] continue to attract attention. Retaining fluorine in a molecule is also desirable from a medicinal chemistry perspective, since fluorine can improve resistance to metabolism due to the strong C-F bond (485 kJmol -1 ) while the small size (van der Waals radius, 1.47 Å) and high electronegativity (3.98 Pauling scale) endow specific electronic properties that can dramatically alter the biological response of the compound [14,15].…”

Synthesis of some fluorinated thiazolopyridine from pentafluoropyridine and 4-phenylsulfonyl tetrafluoropyridine

“…Previously we reported the use of ultrasound irradiation for reaction of pentafluoropyridine with mono-and bidentate Nnucleophiles (Ranjbar-Karimi et al, 2011a). In this paper, we report our investigations on reaction of pentafluoropyridine Synthesis of some fluorinated thiazolopyridine and 4-phenylsulfonyl tetrafluoropyridine with difunctional nitrogen and sulfur nucleophiles and unsymmetrical bidentate nitrogen nucleophiles.…”

Synthesis and structural study of bis-perfluoropyridyl bridged by 1,4 and 1,2 dihydropyridine

“…In previous papers [8,9] we described synthesis of some bispyridyl bridged compounds from reaction of pentafluoropyridine with some equal diamines (primary or secondary). Initial substitution of the fluorine atom located at the most activated 4-position of one pentafluoropyridine molecule is followed by displacement of the 4-position of another pentafluoropyridine molecule leading to bis-perfluoropyridyl bridged products.…”

“…Initial substitution of the fluorine atom located at the most activated 4-position of one pentafluoropyridine molecule is followed by displacement of the 4-position of another pentafluoropyridine molecule leading to bis-perfluoropyridyl bridged products. In this context, we have been developing a general approach to the synthesis of new perfluoroheterocyclic compounds involving reactions between pentafluoropyridine 1 and unequal diamines [8][9][10]. Synthesis of 1D organicinorganic coordination polymers from these bis-perfluoropyridyl bridged compounds is our next goal.…”