Gold(III)-Catalyzed Selective Cyclization of Alkynyl Quinazolinone-Tethered Pyrroles: Synthesis of Fused Quinazolinone Scaffolds

The Journal of Organic Chemistry
Lin-Su WeiGui-Fa Su

Abstract

A series of 1,2- and 2,3-fused quinazolinones have been synthesized in good to excellent yields through gold-catalyzed selective hydroarylations of alkynyl quinazolinone-tethered pyrroles. The studies revealed that 1,2-fused quinazolinones were obtained through a 1,3-rearrangement and sequential 6- exo-trig cyclization of N1-alkynyl quinazolinone-tethered pyrroles, while N3-alkynyl quinazolinone-tethered pyrroles went through 6- exo-dig or 7- endo-dig cyclizations directly to afford 2,3-fused quinazolinones. The fused quinazolinones could be prepared at gram scale in three steps from commercial ortho-aminobenzamide.

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Citations

May 30, 2020·Organic & Biomolecular Chemistry·Prasanjit GhoshSajal Das
May 30, 2019·Frontiers in Chemistry·Marta Marín-LunaCarlos Silva López
Jan 29, 2019·The Journal of Organic Chemistry·Rajendra S RohokaleChepuri V Ramana
Sep 8, 2021·Chemistry : a European Journal·Genesis Infante, Sara Eisler

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