Visible light-induced cascade N-alkylation/amidation reaction of quinazolin-4(3H)-ones and related N-heterocycles

Jiexiong Mai; Ziwei Huang; Shaohuan Lv; Quan Chen; Rongrong Chen; Feng Xie; Jun Wang; Bin Li

doi:10.1039/D2OB02226E

Visible light-induced cascade N-alkylation/amidation reaction of quinazolin-4(3H)-ones and related N-heterocycles

Jiexiong Mai, Ziwei Huang, Shaohuan Lv, Quan Chen, Rongrong Chen, Feng Xie^*, Jun Wang, Bin Li^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

2 Citations (Scopus)

Abstract

An efficient and visible light-promoted cascade N-alkylation/amidation of quinazolin-4(3H)-ones with benzyl halides and allyl halides has been described for the first time to provide a convenient access to quinazoline-2,4(1H,3H)-diones. This cascade N-alkylation/amidation reaction shows good functional group tolerance and could also be applied to N-heterocycles such as benzo[d]thiazoles, benzo[d]imidazoles, and quinazolines. Control experiments show that K2CO3 plays an important role in this transformation.

Original language	English
Pages (from-to)	2423-2428
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	21
Issue number	11
Early online date	27 Feb 2023
DOIs	https://doi.org/10.1039/D2OB02226E
Publication status	Published - 21 Mar 2023

Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/D2OB02226E

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title = "Visible light-induced cascade N-alkylation/amidation reaction of quinazolin-4(3H)-ones and related N-heterocycles",

abstract = "An efficient and visible light-promoted cascade N-alkylation/amidation of quinazolin-4(3H)-ones with benzyl halides and allyl halides has been described for the first time to provide a convenient access to quinazoline-2,4(1H,3H)-diones. This cascade N-alkylation/amidation reaction shows good functional group tolerance and could also be applied to N-heterocycles such as benzo[d]thiazoles, benzo[d]imidazoles, and quinazolines. Control experiments show that K2CO3 plays an important role in this transformation.",

author = "Jiexiong Mai and Ziwei Huang and Shaohuan Lv and Quan Chen and Rongrong Chen and Feng Xie and Jun Wang and Bin Li",

note = "Funding Information: We acknowledge the support of the Foundation of Department of Education of Guangdong Province (no. 2021ZDZX2045, 2020KQNCX093), the Foundation of Wuyi University (no. 2021WGALH06), and the Foundation of Graduate Education Innovation Plan of Guangdong Province (no. YJS-JGXM-21-03). Publisher Copyright: {\textcopyright} 2023 The Royal Society of Chemistry.",

year = "2023",

month = mar,

day = "21",

doi = "10.1039/D2OB02226E",

language = "English",

volume = "21",

pages = "2423--2428",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "11",

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TY - JOUR

T1 - Visible light-induced cascade N-alkylation/amidation reaction of quinazolin-4(3H)-ones and related N-heterocycles

AU - Mai, Jiexiong

AU - Huang, Ziwei

AU - Lv, Shaohuan

AU - Chen, Quan

AU - Chen, Rongrong

AU - Xie, Feng

AU - Wang, Jun

AU - Li, Bin

N1 - Funding Information: We acknowledge the support of the Foundation of Department of Education of Guangdong Province (no. 2021ZDZX2045, 2020KQNCX093), the Foundation of Wuyi University (no. 2021WGALH06), and the Foundation of Graduate Education Innovation Plan of Guangdong Province (no. YJS-JGXM-21-03). Publisher Copyright: © 2023 The Royal Society of Chemistry.

PY - 2023/3/21

Y1 - 2023/3/21

N2 - An efficient and visible light-promoted cascade N-alkylation/amidation of quinazolin-4(3H)-ones with benzyl halides and allyl halides has been described for the first time to provide a convenient access to quinazoline-2,4(1H,3H)-diones. This cascade N-alkylation/amidation reaction shows good functional group tolerance and could also be applied to N-heterocycles such as benzo[d]thiazoles, benzo[d]imidazoles, and quinazolines. Control experiments show that K2CO3 plays an important role in this transformation.

AB - An efficient and visible light-promoted cascade N-alkylation/amidation of quinazolin-4(3H)-ones with benzyl halides and allyl halides has been described for the first time to provide a convenient access to quinazoline-2,4(1H,3H)-diones. This cascade N-alkylation/amidation reaction shows good functional group tolerance and could also be applied to N-heterocycles such as benzo[d]thiazoles, benzo[d]imidazoles, and quinazolines. Control experiments show that K2CO3 plays an important role in this transformation.

UR - http://www.scopus.com/inward/record.url?scp=85149648861&partnerID=8YFLogxK

U2 - 10.1039/D2OB02226E

DO - 10.1039/D2OB02226E

M3 - Journal article

SN - 1477-0520

VL - 21

SP - 2423

EP - 2428

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 11

ER -

Visible light-induced cascade N-alkylation/amidation reaction of quinazolin-4(3H)-ones and related N-heterocycles

Abstract

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