Conformations of 1,3,5-triaryl-1,3,5-triazacyclohexanes: comparison of the o-, m-, and p-fluorophenyl compounds

Abstract

w G 12 8QQ Crystallographic studies of 1,3,5-tris-(0-, m-, and p-fluorophenyl) -1,3,5-triazacyclohexane disclose examples of diaxial-equatorial chair conformations for 1,3,5-triaryl-I ,3,5-triazacyclohexanes. The repulsion between axial aryl groups is relieved by the N-C(aryl) axial bonds being displaced outwards from ideal tetrahedral positions by 17-21'. The orientation of the equatorial aryl ring about the N-C(aryl) bond depends on the position of the F substituent. In the p -F compound the angle between

Green chemical synthesis of fluorinated 1,3,5-triaryl-s-triazines in aqueous medium under microwaves as potential antifungal agents

“…Conventional synthesis: It was synthesized according to literature reported method [18]. 3-Fluoro aniline (1.23 g, 10 mmol) was stirred and heated (oil bath temperature slowly raised from 90 to 102 8C) with para formaldehyde (0.32 g, 10 mmol) in anhydrous benzene (30 ml) with azeotropic removal of water, using Dean and Stark apparatus for 10 h. The remaining benzene was removed under reduced pressure and solid residue was extracted with ether, the ether layer dried (Na 2 SO 4 ) and evaporated under suction to give crude product which was further recrystallized from hexane to give 3a (mp 84-86; yield ¼ 75%) [18].…”

“…Conventional syntheses of tri substituted 1,3,5-triazines suffer from many disadvantages like multistep procedure [6,7], long reaction time, low yield, use of strong acids [6]/ base [18]/dehydrating agents [17], use of high boiling solvents [19] and Dean stark apparatus for azeotropic removal of water [6,7,18].…”

Synthesis and characterization of 1,3-bis(2-fluorophenyl)-5-pentyl-1,3,5-triazinane

“…The resulting oily phase was extracted with CH2Cl2, dried with MgSO4 and evaporated to dryness [3]. The product was solidified on standing after 2 days [7].…”

“…They represent an important class in coordination chemistry [1]. They are used a framework for conformational studies in structural chemistry [2,3].…”

Synthesis and antimicrobial activity of 1,3-bis-butyl-5-(4-iodophenyl)-1,3,5-triazacyclohexane

“…1,3,5-Triazacyclohexanes can be employed as ligands for complexes used as catalyst in the polymerization and trimerization of olefines [3]. Further, the interest in triazacyclohexanes as ligand seems to growing rapidly [4][5][6][7][8].…”