Gold(I)-Catalyzed Intramolecular Bicyclization: Divergent Construction of Quinazolinone and Ampakine Analogues

Chao Liu; Adriano Bolognani; Liangliang Song; Luc Van Meervelt; Vsevolod A. Peshkov; Erik V. Van Der Eycken

doi:10.1021/acs.orglett.2c03547

Gold(I)-Catalyzed Intramolecular Bicyclization: Divergent Construction of Quinazolinone and Ampakine Analogues

Chao Liu
, Adriano Bolognani
, Liangliang Song
, Luc Van Meervelt
, Vsevolod A. Peshkov
, Erik V. Van Der Eycken

KU Leuven
Nanjing Forestry University
College of Chemistry
Soochow University
People's Friendship University of Russia

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

Abstract

A gold(I)-catalyzed cascade intramolecular cyclization of Ugi adducts for the divergent construction of quinazolinone and ampakine analogues has been developed in a rapid, highly efficient and step-economical manner. This protocol shows high yields, excellent functional-group tolerance, broad substrate scope and excellent chemo- and regioselectivity. The practicality of this strategy is further demonstrated by a scale-up reaction. Diverse oligopeptides are also found to be well tolerated, affording polycyclic products decorated with a peptide chain.

Original language	English
Pages (from-to)	8536-8541
Number of pages	6
Journal	Organic Letters
Volume	24
Issue number	46
DOIs	https://doi.org/10.1021/acs.orglett.2c03547
Publication status	Published - Nov 25 2022

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Gold(I)-Catalyzed Intramolecular Bicyclization: Divergent Construction of Quinazolinone and Ampakine Analogues",

abstract = "A gold(I)-catalyzed cascade intramolecular cyclization of Ugi adducts for the divergent construction of quinazolinone and ampakine analogues has been developed in a rapid, highly efficient and step-economical manner. This protocol shows high yields, excellent functional-group tolerance, broad substrate scope and excellent chemo- and regioselectivity. The practicality of this strategy is further demonstrated by a scale-up reaction. Diverse oligopeptides are also found to be well tolerated, affording polycyclic products decorated with a peptide chain.",

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AU - Liu, Chao

AU - Bolognani, Adriano

AU - Song, Liangliang

AU - Van Meervelt, Luc

AU - Peshkov, Vsevolod A.

AU - Van Der Eycken, Erik V.

PY - 2022/11/25

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AB - A gold(I)-catalyzed cascade intramolecular cyclization of Ugi adducts for the divergent construction of quinazolinone and ampakine analogues has been developed in a rapid, highly efficient and step-economical manner. This protocol shows high yields, excellent functional-group tolerance, broad substrate scope and excellent chemo- and regioselectivity. The practicality of this strategy is further demonstrated by a scale-up reaction. Diverse oligopeptides are also found to be well tolerated, affording polycyclic products decorated with a peptide chain.

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ER -

Gold(I)-Catalyzed Intramolecular Bicyclization: Divergent Construction of Quinazolinone and Ampakine Analogues

Abstract

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