One pot conversion of azido arenes to N-arylacetamides and N-arylformamides: synthesis of 1,4-benzodiazepine-2,5-diones and fused [2,1-b]quinazolinones

The Chemistry of Benzodiazepines

“…The introduction of modifications at position 2 leads to chlordiazepoxide (5), metaclazepam (20), and uldazepam (31). The 2-acylaminomethyl derivatives do not have affinity for the same receptor, and therefore lack anxiolytic activity.…”

“…o-Nitroacyl chlorides 76 and o-azidoacyl chlorides 79 [31] can be employed as starting point for the preparation of 1,4-benzodiazepine-2,5-diones. Condensation with an amino ester provides the N-acylated precursors 77 and 80, respectively, that can be cyclized directly into the benzodiazepine-1,3-diones 78 and 81 upon reduction of the masked amine functionality (Scheme 25.12).…”

New synthetic route to pyrimido[4,5-g]quinazoline-4,9-diones

“…7,8 Due to the importance of quinazolinones for biological activity and pharmaceutical relevance, research in the synthesis of various quinazolinones have been conducted. [5][6][7][8][9][10][11][12][13][14][15][16][17] A pyrimido[4,5-g]quinazoline-4,9-dione compound has two quinazolinone moieties fused to a central benzene ring, which allows delocalization of p-electrons between 2 and 7 positions. Its 2,7-(hetero)aryl disubstituted derivatives ( Fig.…”

Tricyclic Quinazoline Alkaloids: Isolation, Synthesis, Chemical Modification, and Biological Activity

“…Scheme 1 shows several of them. For example, they include condensation of anthranilic acid and its esters (43) with lactams in the presence of condensing agents (POCl 3 , SOCl 2 ) [42][43][44]; cyclization with lactime esters [45]; catalyzed reaction of 2-nitro-(azido)-benzoylchlorides (44) with J-butyrolactam (BL) [46,47], and radical cyclization of 3-iodopropylquinazolin-4-one (45) in the presence of hexamethylditin (Me 3 Sn) 2 [48]. It was also prepared from anthranilic acid via a microwave (MW) domino reaction [49].…”