Simple synthesis of quinolines and dibenzo[b,f][1,5]diazocines under microwave irradiation

Chiral exploration of 6,12‐diphenyldibenzo[b,f][1,5]diazocine with stable conformation

“…The racemic (±)‐ 3 was prepared by the self‐condensation of 2‐aminobenzophenone in the presence of P 2 O 5 under solvent‐free conditions . The X‐ray crystal structure of racemic (±)‐ 3 revealed that there are two enantiomers with opposite configurations ( R vs. S ) in the unite cell (Figure a).…”

“…The racemic (AE)-3 was prepared by the self-condensation of 2aminobenzophenone in the presence of P 2 O 5 under solventfree conditions. [25][26][27][28][29][30][31][32][33][34][35][36] The X-ray crystal structure of racemic (AE)-3 38 revealed that there are two enantiomers with opposite configurations (R vs. S) in the unite cell ( Figure 1a). Both of the two molecules adopt the boat conformation similar to a "saddle," where the dibenzo[b,f] [1,5]diazocine parent skeleton looks like a horse blanket with two handles, while the other two phenyl groups look like a pair of stirrups.…”

“…Since the skeleton of benzo[ b , f ][1,5]diazocine was first synthesized more than century ago, substantial efforts have been devoted to the preparation and application of the racemic mixtures . However, to the best of our knowledge, the chirality of this type of compound has not been investigated yet.…”

“…Since the skeleton of benzo[b,f] [1,5]diazocine was first synthesized more than century ago, 24 substantial efforts have been devoted to the preparation and application of the racemic mixtures. [25][26][27][28][29][30][31][32][33][34][35][36] However, to the best of our knowledge, the chirality of this type of compound has not been investigated yet. Herein, we report the successful optical resolution of 3 and experimental determination of absolute configurations of its enantiomers and the properties directly connected to their chirality.…”

Synthesis and Spectral Characterization of Benzo-[6,7][1,5]diazocino[2,1-a]isoindol-12-(14H)-one Derivatives

“…As a result, the usual synthetic strategies for the preparation of other ring systems cannot always be applied to eight-membered rings. Several conventional approaches such as intramolecular cyclization, intermolecular cyclization, palladium-catalyzed, Ugi Four-Center Three-Component coupling reaction (U-4C-3CR), use of microwave radiation, Morita–Baylis–Hillman reaction and intramolecular Friedel–Crafts strategies have been reported in the literature [17,18,19,20,21,22,23,24,25,26,27]. Despite the large number of literature reports on the conventional synthesis of diazocine skeletons, these conventional methods suffer from some drawbacks such as long reaction times, harsh reaction conditions, low-product yields, high cost, toxic by-products and use of toxic catalysts.…”