Substrate Directed C–H Activation for the Synthesis of Benzo[c]cinnolines through a Sequential C–C and C–N Bond Formation

Abstract

A wide range of benzo[c]cinnolines are prepared through a sequential C-C and C-N bond formation by means of an oxidative C-H functionalization. The reaction proceeds via the C-arylation of 1-arylhydrazine-1,2-dicarboxylate with aryl iodide using Pd(OAc)2/AgOAc followed by an oxidative N-arylation in the presence of PhI/oxone in trifluoroacetic acid. It is entirely a new strategy to generate the benzo[c]cinnoline libraries with a diverse substitution pattern.

Selective Oxidation of Sulfides in Flow Chemistry

“…Increasing the concentration of the sulfide solution to either 0.1, 0.15 or 0.2 M ( Table 1, entries 2-4) did not affect the conversion of the reaction. [21] The packed-bed reactor with oxone contains approximately 9.1 mmol oxone (5.6 g) and can be used to oxidize up to 10 mmol of sulfide without affecting the conversion and with no change in residence time. The volume percentage of trifluoroacetic acid in dichloromethane was crucial for obtaining high conversion.…”

Sultams: Recent Syntheses and Applications

“…[35] In the proposed mechanism, the rearrangement proceeds by way of a 1,5-rhodium shift from C(sp 3 ) to C(sp 2 ) as shown in Kumara Swamy and co-worker reported a new and efficient one-pot protocol for the synthesis of benzosultams 39.2 or 39.3 through Cu-catalyzed tandem cyclization of functionalized ynamides 39.1 with elemental sulfur or selenium (Scheme 39). [36] The mechanism of this reaction was established through control experiments based on earlier reports (Scheme 40). Recently, Yu et al synthesized biaryl sultams 41.2 with the aid of visible-light promoted denitrogenative cyclization of 1,2,3,4-benzothiatriazine 1,1-dioxides 41.1.…”

Simple Synthetic Method for the Functionalized Benzo[c]cinnolines

“…Benzo[ c ]cinnolines are very important structural motifs that have numerous applications owing to their unique physical and biological properties, which include antimicrobial, herbicidal, anticancer, and cytotoxic activities . Many functional materials such as dyes, electrochromic polymers,, fluorescence quenching materials, and medicines contain the benzo[ c ]cinnoline moiety, as shown in Figure .…”