Stepwise construction of a 4-hydroxyphenyl functionalized O,N,N-tridentate ferrocene-containing enaminone: Spectral, analytical and structural studies

A facile access to new diazepines derivatives: Spectral characterization and crystal structures of 7-(thiophene-2-yl)-5-(trifluoromethyl)-2,3-dihydro-1 H -1,4-diazepine and 2-thiophene-4-trifluoromethyl-1,5-benzodiazepine

“…This is corroborated by the 29.2° reduction of the bond angle at the central methine/methylene carbon on passing from 2 to 3 (Tables 2 and 3). Table 2 Selected bond distances (Å) and angles (°) for compound (23) 1.443 (9) C(32)-C (33) 1.450 (10) C(3)-C (4) 1.385 (10) M A N U S C R I P T Table 3 Selected bond distances (Å) and angles (°) for compound 3 3A 3B Bond distances C(2)-C (3) 1.514 (3) C ( (14) 1.411(3)…”

“…Thus, it is attractive to obtain new heterocycles with potential biological properties from easy and minimum step reactions, involving inexpensive starting materials such as -diketones which can be functionalized in three different sites of the molecule. In the last few years, our groups have been interested in the synthesis of -diketones [5][6][7] as starting materials to be used in the preparation of heterocycles [8,9] and tridentate Schiff base ligands [10][11][12], via condensation with aliphatic M A N U S C R I P T…”

Molecular and Solid State Structure of the Doubly-Substituted B-Diketone 3,3'-Bis(ferrocenylmethyl)pentane-2,4-Dione#

“…7,8 On the other hand, β-diketones are attractive building blocks for the construction of polydentate Schiff bases, and both the parent derivative 2,4-pentanedione (CH 3 COCH 2 COCH 3 ), [9][10][11][12] and its organometallic counterpart ferrocenoylacetone (FcCOCH 2 COCH 3 , 13 Fc = (h 5 -C 5 H 5 )Fe(h 5 -C 5 H 4 )) have been widely employed to prepare tridentate Schiff base complexes, also called half-units, upon mono-condensation with primary diamines. [14][15][16][17][18][19][20][21][22] In pursuit of our research work aimed at extending the scope of acyclic Schiff base metalloligands, [14][15][16][17] we decided to synthetize new β-diketones functionalized at the central carbon of the 1,3-dione system, using cerium(IV) ammonium nitrate (CAN), a versatile reagent in a variety of synthetic transformations through oxidation of organic molecules, [23][24][25] as catalyst in the carbon-carbon bond formation between ferrocenyl alcohol substrates and 1,3-diketones. 26 Accordingly, we were able to isolate and structurally characterize three new chiral ferrocene-containing diketones starting from 1-ferrocenyl ethanol.…”

Octahedral bis(2-thenoyltrifluoroacetonato)-ethylenediamine Co(II), Ni(II) and Cu(II) complexes: Synthetic, structural, electrochemical, and theoretical studies

“…Formation of heterocyclic species, namely, 1,4-diazepine and 1,5-benzodiazepine, was indeed observed when 2-thenoyltrifluoroacetone was reacted with 1,2-diaminoethane (en) and 1,2-diaminophenyl, respectively [30], instead of the desired 2-thienyl-containing ONN-tridentate 4 Schif base hemiligands [25,31,32]. Thus, in the quest to prepare thienyl-containing N 2 O 2 tetradentate Schiff base compounds, we attempted condensation reactions by using readily available bis [4,4,4- Schiff base complex [33].…”

“…In the last few years, we have prepared different kinds of β-diketones [24][25][26] to be used as precursor for the preparation of several Schiff base ligands [25], metal complexes [27] and Schiff base oligomers [28]. Such condensation reactions proceed via the nucleophilic addition of the primary amine onto the carbonyl carbon giving a hemiaminal -C(OH)(NHR)-intermediate which, depending on the functional groups (R) and the experimental conditions evolves to the formation of a heterocyclic or a polydentate Schiff base compound [29].…”