A Route to Azafluoranthene Natural Products Through Direct Arylation

Abstract

Microwave-assisted direct arylation was successfully employed in the synthesis of azafluoranthene alkaloids for the first time. Direct arylation reactions on a diverse set of phenyltetrahydroisoquinolines produces the indeno[1,2,3-ij]isoquinoline nucleus en route to a high yielding azafluoranthene synthesis. The method was used as a key step in the efficient preparation of the natural products rufescine and triclisine. As demonstrated herein, this synthetic approach should be generally applicable to the preparation of natural and un-natural azafluoranthene alkaloids as well as “azafluoranthene-like” isoquinoline alkaloids.

Genus Caulophyllum: An Overview of Chemistry and Bioactivity

“…magnoflorine ( 1 ), taspine ( 2 ), and boldine ( 3 ) are contributed to aporphine alkaloids. Aporphine alkaloids have been shown to possess anticancer activity and there is evidence that this activity is exerted through induction of apoptosis, inhibiting cell proliferation and inhibiting DNA topoisomerase [ 23 , 24 ]. Magnoflorine ( 1 ), a quaternary ammonium base, is isolated and detected with the biggest amounts among all the alkaloids isolated from genus Caulophyllum .…”

Synthesis of hexahydrocyclopenta[ij]isoquinolines as a new class of dopaminergic agents

“…The HCPIQ system constitutes the nucleus of the naturally occurring proaporphines (pronuciferin type) [26,27], and besides, this system is structurally related to the azafluoranthene alkaloids ( Fig. 1) [28]. Although HCPIQs constitute a small group into the IQ alkaloids, several synthesis have been reported [29e34] given their potential and useful biological properties, including the inhibition of phenylethanolamine N-methyltransferase (PNMT) [29] and poly(ADP-ribose) polymerases (PARPs) [30] enzymes, as well as their antiprotozoal [35] activities.…”

Ternary organic solar cells doped methoxyphenyl indenopyrazoloquinoline derivatives

“…halo-pyrazolo [3,4-b]quinolines 1a-c, the right precursors by means of palladium coupling reactions were converted into indenopyrazoloquinoline (azafluoranthene) derivatives [25] (Fig. 2).…”