Divergent Synthesis of Novel Dienylbenzothiazoles and Arylidenedibenzoxazepines and Evaluation of Their Antiproliferative and Cytotoxic Properties

Copper-Catalyzed Synthesis of Dibenzo[b,f]imidazo[1,2-d][1,4]oxazepine Derivatives via a Double Ullmann Coupling Reaction

“…Certainly, a lot of other efficient methods have been developed recently for access to dibenzooxazepines. 6 In very recent years (Scheme 1, c), an intramolecular hydroamination of 4,5-diphenyl-2-(2-(prop-2-yn-1yloxy)phenyl)-1H-imidazoles in DMF to synthesize benzo [f]imidazo [1,2-d] [1,4]oxazepines was realized using Ag-NO 3 as a catalyst. 7 However, these methods have, more or less, some disadvantages, such as low yields (56-70%), nonavailability of raw materials or costly catalysts (Pd).…”

“…7 However, these methods have, more or less, some disadvantages, such as low yields (56-70%), nonavailability of raw materials or costly catalysts (Pd). Moreover, as far as we know, there is no literature concerning the construction of dibenzoimidazo [1,4]oxazepines.…”

“…Oxazepine derivatives are known to possess good pharmacological and biological activities including antiproliferative, 1 anticancer 2 and antitumor 3 activity. Therefore, much attention has been devoted to the synthesis of structurally modified [1,4]oxazepines, especially benzo-and heterocyclo-fused [1,4]oxazepines. Of these, imidazo [1,4]oxazepines and dibenzooxazepines are two of the most important types of molecules in medicinal chemistry.…”

“…Therefore, much attention has been devoted to the synthesis of structurally modified [1,4]oxazepines, especially benzo-and heterocyclo-fused [1,4]oxazepines. Of these, imidazo [1,4]oxazepines and dibenzooxazepines are two of the most important types of molecules in medicinal chemistry. The former structure was obtained successfully by an intramolecular etherification of 2-(1-(2-hydroxyethyl)-5-nitro-1H-imidazol-2-yl)-1-phenylethan-1-ones in the presence of 50% H 2 SO 4 (Scheme 1, a), but the reactants are not easily available.…”

“…The former structure was obtained successfully by an intramolecular etherification of 2-(1-(2-hydroxyethyl)-5-nitro-1H-imidazol-2-yl)-1-phenylethan-1-ones in the presence of 50% H 2 SO 4 (Scheme 1, a), but the reactants are not easily available. 4 Scheme 1 Approaches to [1,4]…”