Hexachlorocyclotriphosphazene (HCCP)-Mediated Direct Formation of Thioethers and Ethers from Quinazolin-4(3H)-ones

被引：7

作者：

Hu, Baoxiang ^{[1
]}

Zhang, Xiaochu ^{[1
]}

Sheng, Lili ^{[1
]}

Guo, Ming ^{[2
]}

Shen, Zhenlu ^{[1
]}

Hu, Xinquan ^{[1
]}

Sun, Nan ^{[1
]}

Mo, Weimin ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn & Mat Sci, State Key Lab Breeding Base Green Chem Synth Tech, Hangzhou 310014, Zhejiang, Peoples R China

[2] Zhejiang Agr & Forestry Univ, Dept Chem, Linan 311300, Peoples R China

来源：

MOLECULES | 2013年 / 18卷 / 05期

关键词：

quinazolin-4(3H)-ones; hexachlorocyclotriphosphazene; 4-arylthioquinazolines; 4-aryloxyquinazolines; 4-alkoxyquinazolines; PARASITE PLASMODIUM-FALCIPARUM; BIOLOGICAL EVALUATION; POTENT; INHIBITORS; AGENTS; QUINAZOLINES; DERIVATIVES; DISCOVERY; UREAS; IDENTIFICATION;

D O I：

10.3390/molecules18055580

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A hexachlorocyclotriphosphazene (HCCP)-mediated direct formation of quinazoline (thio) ethers from quinazolin-4(3H)-ones has been developed. Treatment of quinazolin-4(3H)-ones with HCCP, diisopropylethylamine (DIPEA), and thiophenols resulted in formation of the corresponding 4-arylthioquinazoline derivatives in moderate to excellent yields. This method has also been utilized to prepare 4-aryloxyquinazoline and 4-alkoxyquinazoline derivatives using phenols and sodium alkoxides as the nucleophiles.

引用

页码：5580 / 5593

页数：14

共 50 条

[1] An efficient HCCP-mediated direct amination of quinazolin-4(3H)-ones
Shen, Zhenlu
He, Xiaofei
Dai, Jialiang
Mo, Weimin
Hu, Baoxiang
Sun, Nan
Hu, Xinquan
TETRAHEDRON, 2011, 67 (09) : 1665 - 1672
[2] Molybdenum-mediated synthesis of quinazolin-4(3H)-ones via cyclocarbonylation using microwave irradiation
Roberts, Bryan
Liptrot, David
Luker, Tim
Stocks, Michael J.
Barber, Catherine
Webb, Nicola
Dods, Robert
Martin, Barrie
TETRAHEDRON LETTERS, 2011, 52 (29) : 3793 - 3796
[3] Lemon Juice Mediated Synthesis of 3-Substituted Quinazolin-4(3H)-Ones and their Pharmacological Evaluation
Prasad, Malavattu G.
Lakshmi, C. Vijaya
Katari, Naresh K.
Jonnalagadda, Sreekantha B.
Pal, Manojit
ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY, 2019, 19 (16) : 2001 - 2009
[4] Synthesis of Quinazolin-4(3H)-ones via a novel approach
Akbari, Ali
Zahedifar, Mahboobeh
JOURNAL OF SAUDI CHEMICAL SOCIETY, 2023, 27 (02)
[5] Quinazolin-4(3H)-ones and 5,6-Dihydropyrimidin-4(3H)-ones from β-Aminoamides and Orthoesters
Gavin, Joshua T.
Annor-Gyamfi, Joel K.
Bunce, Richard A.
MOLECULES, 2018, 23 (11):
[6] SYNTHESIS OF BENZOXAZOLYLTHIOMETHYL AND BENZTHIAZOLYLTHIOMETHYL QUINAZOLIN-4(3H)-ONES
Rafeeq, Mohammad
Reddy, Chittireddy Venkata Ramana
Dubey, Pramod Kumar
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2015, 190 (11) : 1857 - 1864
[7] Novel Quinolone Substituted Quinazolin-4(3H)-Ones as Anti-Inflammatory, Anticancer Agents: Synthesis and Biological Screening
Kumar, Santosh
Aghara, Jignesh Chhaganbhai
Alex, Angel Treasa
Aranjani, Jesil Mathew
Joesph, Alex
INDIAN JOURNAL OF PHARMACEUTICAL EDUCATION AND RESEARCH, 2018, 52 (04) : S268 - S276
[8] Convenient synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones: applications towards the synthesis of drugs
Kumar, Dinesh
Jadhavar, Pradeep S.
Nautiyal, Manesh
Sharma, Himanshu
Meena, Prahlad K.
Adane, Legesse
Pancholia, Sahaj
Chakraborti, Asit K.
RSC ADVANCES, 2015, 5 (39) : 30819 - 30825
[9] Formation of quinazolin-4(3H)-ones from N-sulfonoketenimines and 2-aminobenzamides
Yavari, Issa
Akbarzadeh, Somayeh
Ghorbanzadeh, Meysam
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2024, 21 (4) : 1011 - 1019
[10] ONE-POT SYNTHESIS OF 4-AMINOQUINAZOLINES BY HEXAMETHYLDISILAZANE-MEDIATED REACTION OF QUINAZOLIN-4(3H)-ONES WITH AMINES
Shen, Zhen-Lu
He, Xiao-Fei
Hong, Yi-Ming
Hu, Xin-Quan
Mo, Wei-Min
Hu, Bao-Xiang
Sun, Nan
SYNTHETIC COMMUNICATIONS, 2011, 41 (24) : 3644 - 3653

← 1 2 3 4 5 →