Transition metal-promoted synthesis of 2-aryl/heteroaryl-thioquinazoline: C-S Bond formation by "Chan-Lam Cross-Coupling" Reaction

被引：18

作者：

Pulakhandam, Satya Karuna ^{[1
]}

Katari, Naresh Kumar ^{[2
]}

Manda, Ravi Prakash Reddy ^{[3
]}

机构：

[1] Jawaharlal Nehru Technol Univ Kakinada, Kakinada 533003, Andhra Pradesh, India

[2] GITAM Univ, GITAM Sch Technol, Dept Chem, HTP Campus, Medak 502329, Telangana, India

[3] C MET, IDA Phase 2,HCL PO, Hyderabad 500051, Telangana, India

来源：

JOURNAL OF CHEMICAL SCIENCES | 2017年 / 129卷 / 02期

关键词：

Chan-Lam coupling; quinazoline; boronic acids; copper acetate; ARYLBORONIC ACIDS; DOMINO REACTIONS; ETHERS; ARYLATION; CARBON; SCOPE;

D O I：

10.1007/s12039-016-1217-7

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient method for the synthesis of S-aryl/heteroaryl-quinazoline has been developed through the cross-coupling of 1,4-dihydroquinazoline with a variety of aryl and heteroaryl boronic acids assisted by [Cu(OAc)(2)] as the catalyst for the formation of carbon-sulfur bonds. This newly developed method demonstrates that the conditions of the traditional copper-catalyzed Chan-Lam reaction can be improved. Optimized reaction involves base, solvent and catalyst.

引用

页码：203 / 210

页数：8

共 11 条

[1] Transition metal-promoted synthesis of 2-aryl/heteroaryl-thioquinazoline: C-S Bond formation by “Chan-Lam Cross-Coupling” Reaction
SATYA KARUNA PULAKHANDAM
NARESH KUMAR KATARI
RAVI PRAKASH REDDY MANDA
Journal of Chemical Sciences, 2017, 129 : 203 - 210
[2] Chan-Lam cross-coupling reaction based on the Cu2S/TMEDA system
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[3] CO2-promoted oxidative cross-coupling reaction for C-S bond formation via masked strategy in an odourless way
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Ge, Nanyang
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[4] Visible-Light-Promoted C-S Cross-Coupling Reaction for Synthesis of Aromatic Thioethers
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ORGANIC SYNTHESES, 2023, 100 : 234 - +
[5] Iodine-Promoted Synthesis of 4-Aryl-2-(arylsulfonyl)quinolones by Desulfurative C-S Cross-Coupling Reaction of Quinoline-2-thiones with Sodium Sulfinates
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[6] Copper-Catalyzed Synthesis of O/N-Alkyl S-Phenyl Phenylcarbamothioates: An Odorless and Chemo-selective Chan-Lam Reaction to Construct C-S Bond
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Wang, Xi
Li, Jing-Hang
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[7] Transition-Metal-Free, Visible-Light-Promoted C-S Cross-Coupling through Intermolecular Charge Transfer
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Lim, Chern-Hooi
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SYNLETT, 2018, 29 (19) : 2449 - 2455
[8] Chemo-Controlled Cross-Coupling of Di(hetero)aryl Disulfides with Grignard Reagents: C-C vs. C-S Bond Formation
Du, Bao-Xin
Quan, Zheng-Jun
Da, Yu-Xia
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ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (06) : 1270 - 1276
[9] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges
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Ananikov, Valentine P.
CHEMICAL REVIEWS, 2022, 122 (21) : 16110 - 16293
[10] Utilizing 2-phenylpropanal as coupling partner for C-S bond formation via sequential thioarylation and decarbonylation process: A novel strategy for the synthesis of aryl alkyl sulfides
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APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (11)

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