Carbene-Catalyzed N,N-Nucleophilic Activation of Thioureas for Access to Pyrimidinthione Derivatives

Liya Cao; Tingting Li; Yonggui Robin Chi; Zhichao Jin

doi:10.1002/ajoc.202100113

Carbene-Catalyzed N,N-Nucleophilic Activation of Thioureas for Access to Pyrimidinthione Derivatives

Liya Cao, Tingting Li, Yonggui Robin Chi, Zhichao Jin^*

^*Corresponding author for this work

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

6 Citations (Scopus)

Abstract

An N-heterocyclic carbene-catalyzed [3+3] cycloaddition reaction of acylthioureas with ynals is reported. Both N atoms in the thiourea substrate are activated as nucleophiles and incorporated inside the ring system of the product. Pyrimidinthione derivatives bearing various substituents and substitution patterns are afforded as the products in moderate to good yields.

Original language	English
Pages (from-to)	1090-1093
Number of pages	4
Journal	Asian Journal of Organic Chemistry
Volume	10
Issue number	5
DOIs	https://doi.org/10.1002/ajoc.202100113
Publication status	Published - May 2021
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2021 Wiley-VCH GmbH

ASJC Scopus Subject Areas

Organic Chemistry

Keywords

acetylenic acylazolium intermediate
N,N-dinucleophilic activation
N-heterocyclic carbenes
nucleophilic addition
organocatalysis

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10.1002/ajoc.202100113

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title = "Carbene-Catalyzed N,N-Nucleophilic Activation of Thioureas for Access to Pyrimidinthione Derivatives",

abstract = "An N-heterocyclic carbene-catalyzed [3+3] cycloaddition reaction of acylthioureas with ynals is reported. Both N atoms in the thiourea substrate are activated as nucleophiles and incorporated inside the ring system of the product. Pyrimidinthione derivatives bearing various substituents and substitution patterns are afforded as the products in moderate to good yields.",

keywords = "acetylenic acylazolium intermediate, N,N-dinucleophilic activation, N-heterocyclic carbenes, nucleophilic addition, organocatalysis",

author = "Liya Cao and Tingting Li and Chi, {Yonggui Robin} and Zhichao Jin",

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month = may,

doi = "10.1002/ajoc.202100113",

language = "English",

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T1 - Carbene-Catalyzed N,N-Nucleophilic Activation of Thioureas for Access to Pyrimidinthione Derivatives

AU - Cao, Liya

AU - Li, Tingting

AU - Chi, Yonggui Robin

AU - Jin, Zhichao

PY - 2021/5

Y1 - 2021/5

N2 - An N-heterocyclic carbene-catalyzed [3+3] cycloaddition reaction of acylthioureas with ynals is reported. Both N atoms in the thiourea substrate are activated as nucleophiles and incorporated inside the ring system of the product. Pyrimidinthione derivatives bearing various substituents and substitution patterns are afforded as the products in moderate to good yields.

AB - An N-heterocyclic carbene-catalyzed [3+3] cycloaddition reaction of acylthioureas with ynals is reported. Both N atoms in the thiourea substrate are activated as nucleophiles and incorporated inside the ring system of the product. Pyrimidinthione derivatives bearing various substituents and substitution patterns are afforded as the products in moderate to good yields.

KW - acetylenic acylazolium intermediate

KW - N,N-dinucleophilic activation

KW - N-heterocyclic carbenes

KW - nucleophilic addition

KW - organocatalysis

UR - http://www.scopus.com/inward/record.url?scp=85103543728&partnerID=8YFLogxK

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U2 - 10.1002/ajoc.202100113

DO - 10.1002/ajoc.202100113

M3 - Article

AN - SCOPUS:85103543728

SN - 2193-5807

VL - 10

SP - 1090

EP - 1093

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 5

ER -

Carbene-Catalyzed N,N-Nucleophilic Activation of Thioureas for Access to Pyrimidinthione Derivatives

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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