Gold(I)-Catalyzed Tandem Synthesis of Polycyclic Dihydroquinazolinones

Abstract

A gold-catalyzed cascade process for the synthesis of dihydroquinazolinone scaffolds was developed. A series of gold catalysts were screened for this tandem transformation, and the (PPh3)AuCl/AgOTf catalyst combination was found to be the best catalyst system. This method is characterized by good yields, high regioselectivity, and broad substrate scope. This method is also applicable to the synthesis of tetracyclic dihydroquinazolinones and seven-membered ring-fused dihydroquinazolinones.

Advances in gold catalyzed synthesis of quinoid heteroaryls

“…The synthesis of double-cyclized product 1h and regeneration of the cationic gold catalyst A was facilitated by the re-coordination of A to enamine intermediate D , which in turn helped the second intramolecular cyclization. 65…”

“…This complex can then be hydrated to create ketone 2B or cyclized to form gold-alkyl complex C. Active catalyst A was renewed by the protodeauration of C, which released enamine intermediate D. The synthesis of double-cyclized product 1h and regeneration of the cationic gold catalyst A was facilitated by the re-coordination of A to enamine intermediate D, which in turn helped the second intramolecular cyclization. 65 …”

Fast quinazolinone synthesis by combining enzymatic catalysis and photocatalysis

“…1) [1][2][3]. For example, febrifugine has a potent antimalarial activity [4][5][6], while luotonin [7] has been reported to exhibit anti-cancer activity [8][9][10][11] through the inhibition of human topoisomerase-I. Furthermore, halofuginone coccidiostat [12,13] turned out to be cytotoxic against human leukemia K562 and colon cancer SW1116 cell lines, while bouchardatine [14] has shown anti-cancer [15,16] effects.…”