Ready access to 7,8-dihydroindolo[2,3-d][1]benzazepine-6(5H)-one scaffold and analogues via early-stage Fischer ring-closure reaction

• Irina Kuznetcova,
• Felix Bacher,
• Daniel Vegh,
• Hsiang-Yu Chuang and
• Vladimir B. Arion

Beilstein J. Org. Chem. 2022, 18, 143–151, doi:10.3762/bjoc.18.15

• -phenylhydrazine in acetic acid that delivers methyl 2-(1-benzyl-3-(2-nitrophenyl)-1H-indol-2-yl)acetate in 55% yield. Keywords: anticancer; Fischer indole synthesis; Heck reaction; heterocyclic compounds; indolobenzazepines; latonduines; paullones; Introduction Indolobenzazepines are fused heterocyclic

• scaffolds with versatile medicinal properties, including anti-Alzheimer, anti-inflammatory, anticancer, antidiabetic, and antileishmanial activity [1]. Since the first synthesis of paullones (scaffold A in Figure 1) in 1992 [2], and disclosure of their Cdk inhibiting potential, several other analogues were

• designed and prepared [3], with the hope of developing more efficient anticancer drugs with either improved Cdk targeting or with a different mechanism of action [4][5]. The isomers B and D (Figure 1) are synthetic derivatives of paullones, in which either the lactam unit is shifted (B) or both the lactam

Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles

• Takashi Go,
• Akane Morimatsu,
• Hiroaki Wasada,
• Genzoh Tanabe,
• Osamu Muraoka,
• Yoshiharu Sawada and
• Mitsuhiro Yoshimatsu

Beilstein J. Org. Chem. 2018, 14, 2722–2729, doi:10.3762/bjoc.14.250

• frameworks present in marine natural products [1][2] such as hymenialdisines [3][4], latonduines [5], paullones, kenpaullones and alsterpaullones [6][7]. These compounds can be used for various pharmaceutical applications [8] such as for the treatment of neurodegenerative and proliferative disorders. These