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

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

17 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

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Copyright © 2020 American Chemical Society.

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title = "One-Pot Synthesis of 1-Hydroxyacridones from para-Quinols and ortho-Methoxycarbonylaryl Isocyanates",

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.",

author = "Jing Wu and Jinzhu Zhang and Ruben Soto-Acosta and Lili Mao and Jiahui Lian and Kenny Chen and Guy Pillon and Guoqi Zhang and Geraghty, \{Robert J.\} and Shengping Zheng",

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = mar,

day = "20",

doi = "10.1021/acs.joc.9b03307",

language = "English (US)",

volume = "85",

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TY - JOUR

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

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.

UR - https://www.scopus.com/pages/publications/85082144991

UR - https://www.scopus.com/pages/publications/85082144991#tab=citedBy

U2 - 10.1021/acs.joc.9b03307

DO - 10.1021/acs.joc.9b03307

M3 - Article

C2 - 32070098

AN - SCOPUS:85082144991

SN - 0022-3263

VL - 85

SP - 4515

EP - 4524

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6

ER -

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

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