One-Pot Synthesis of 1-Hydroxyacridones from para-Quinols and ortho-Methoxycarbonylaryl Isocyanates

Jing Wu; Jinzhu Zhang; Ruben Soto-Acosta; Lili Mao; Jiahui Lian; Kenny Chen; Guy Pillon; Guoqi Zhang; Robert J. Geraghty; Shengping Zheng

doi:10.1021/acs.joc.9b03307

One-Pot Synthesis of 1-Hydroxyacridones from para-Quinols and ortho-Methoxycarbonylaryl Isocyanates

Jing Wu, Jinzhu Zhang, Ruben Soto-Acosta, Lili Mao, Jiahui Lian, Kenny Chen, Guy Pillon, Guoqi Zhang, Robert J. Geraghty, Shengping Zheng

Center for Drug Design

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

12 Scopus citations

Abstract

A variety of substituted acridones were synthesized via a one-pot, metal-free cascade reaction. In this event, the DBU-mediated addition between quinols and ortho-methoxycarbonylaryl isocyanates formed a bicyclic oxazolidinone, followed by a sequence of intramolecular condensation, tautomerization, and decarboxylation, which led to the formation of acridones. The acridones showed mild activity against the human cytomegalovirus.

Original language	English (US)
Pages (from-to)	4515-4524
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	85
Issue number	6
DOIs	https://doi.org/10.1021/acs.joc.9b03307
State	Published - Mar 20 2020

Bibliographical note

Funding Information:
We are grateful to Professors Richard Franck and Klaus Grohmann at Hunter College for helpful discussions. We also thank Drs. Barney Yoo, Matthew Devany, Michelle Neary, and Tony Hu for mass spectrometric, NMR spectroscopic, and X-ray crystallographic assistance, respectively. Financial support from the Bertha and Louis Weinstein Research Grant, NIH (SC2GM100783), NSF (CHE-1464543), and PSC–CUNY Research Award is gratefully acknowledged.

Publisher Copyright:
Copyright © 2020 American Chemical Society.

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abstract = "A variety of substituted acridones were synthesized via a one-pot, metal-free cascade reaction. In this event, the DBU-mediated addition between quinols and ortho-methoxycarbonylaryl isocyanates formed a bicyclic oxazolidinone, followed by a sequence of intramolecular condensation, tautomerization, and decarboxylation, which led to the formation of acridones. The acridones showed mild activity against the human cytomegalovirus.",

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T1 - One-Pot Synthesis of 1-Hydroxyacridones from para-Quinols and ortho-Methoxycarbonylaryl Isocyanates

AU - Wu, Jing

AU - Zhang, Jinzhu

AU - Soto-Acosta, Ruben

AU - Mao, Lili

AU - Lian, Jiahui

AU - Chen, Kenny

AU - Pillon, Guy

AU - Zhang, Guoqi

AU - Geraghty, Robert J.

AU - Zheng, Shengping

N1 - Funding Information: We are grateful to Professors Richard Franck and Klaus Grohmann at Hunter College for helpful discussions. We also thank Drs. Barney Yoo, Matthew Devany, Michelle Neary, and Tony Hu for mass spectrometric, NMR spectroscopic, and X-ray crystallographic assistance, respectively. Financial support from the Bertha and Louis Weinstein Research Grant, NIH (SC2GM100783), NSF (CHE-1464543), and PSC–CUNY Research Award is gratefully acknowledged. Publisher Copyright: Copyright © 2020 American Chemical Society.

PY - 2020/3/20

Y1 - 2020/3/20

N2 - A variety of substituted acridones were synthesized via a one-pot, metal-free cascade reaction. In this event, the DBU-mediated addition between quinols and ortho-methoxycarbonylaryl isocyanates formed a bicyclic oxazolidinone, followed by a sequence of intramolecular condensation, tautomerization, and decarboxylation, which led to the formation of acridones. The acridones showed mild activity against the human cytomegalovirus.

AB - A variety of substituted acridones were synthesized via a one-pot, metal-free cascade reaction. In this event, the DBU-mediated addition between quinols and ortho-methoxycarbonylaryl isocyanates formed a bicyclic oxazolidinone, followed by a sequence of intramolecular condensation, tautomerization, and decarboxylation, which led to the formation of acridones. The acridones showed mild activity against the human cytomegalovirus.

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JF - Journal of Organic Chemistry

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One-Pot Synthesis of 1-Hydroxyacridones from para-Quinols and ortho-Methoxycarbonylaryl Isocyanates

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