Quinazoline Synthesis via Rh(III)-Catalyzed Intermolecular C-H Functionalization of Benzimidates with Dioxazolones

被引：124

作者：

Wang, Jie ^{[1
]}

Zha, Shanke ^{[1
]}

Chen, Kehao ^{[1
]}

Zhang, Feifei ^{[1
]}

Song, Chao ^{[1
]}

Zhu, Jin ^{[1
]}

机构：

[1] Nanjing Univ, State Key Lab Coordinat Chem, Nanjing Natl Lab Microstruct, Dept Polymer Sci & Engn,Sch Chem & Chem Engn, Nanjing 210093, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 09期

基金：

中国国家自然科学基金;

关键词：

N-N BOND; EFFICIENT SYNTHESIS; DIRECTING GROUP; 2-SUBSTITUTED QUINAZOLINES; DEHYDROGENATIVE SYNTHESIS; REGIOSELECTIVE SYNTHESIS; ANTIBACTERIAL ACTIVITY; SUBSTITUTED PYRIDINES; CYCLIZATION REACTIONS; UNPROTECTED INDOLES;

D O I：

10.1021/acs.orglett.6b00691

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient double C-N bond formation sequence to prepare highly substituted quinazolines utilizing benzimidates and dioxazolones under the catalytic redox-neutral [Cp*RhCl2](2)/AgBF4 system, where dioxazolones could work as an internal oxidant to maintain the catalytic cycle, is reported. N-Unsubstituted imine not only acts as a directing group but also functions as a nucleophile in postcoupling cyclization, and dioxazolone acts as a coupling partner for access to heterocycle.

引用

页码：2062 / 2065

页数：4

共 103 条

[1] Design and Synthesis of Some 3-Substituted-2[(2,4-dichlorophenoxy)-methyl]quinazolin-4(3H)-one Derivatives as Potential Anticonvulsant Agents [J].

Abbas, Safinaz El-Sayed ;

Awadallah, Fadi Mohsen ;

Ibrahim, Nashwa Ahmed ;

Said, Eman Gaber ;

Kamel, Gihan .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2013, 61 (07) :679-687

[2] Cationic Ruthenium(II) Catalysts for Oxidative C-H/N-H Bond Functionalizations of Anilines with Removable Directing Group: Synthesis of Indoles in Water [J].

Ackermann, Lutz ;

Lygin, Alexander V. .

ORGANIC LETTERS, 2012, 14 (03) :764-767

[3] Ruthenium-Catalyzed C-H/N-O Bond Functionalization: Green Isoquinolone Syntheses in Water [J].

Ackermann, Lutz ;

Fenner, Sabine .

ORGANIC LETTERS, 2011, 13 (24) :6548-6551

[4] Ruthenium-Catalyzed Synthesis of lsoquinolones with 8-Aminoquinoline as a Bidentate Directing Group in C-H Functionalization [J].

Allu, Srinivasarao ;

Swamy, K. C. Kumara .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09) :3963-3972

[5] Design, synthesis, and biological evaluation of prazosin-related derivatives as multipotent compounds [J].

Antonello, A ;

Hrelia, P ;

Leonardi, A ;

Marucci, G ;

Rosini, M ;

Tarozzi, A ;

Tumiatti, V ;

Melchiorre, C .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (01) :28-31

[6] Dual kinase inhibition in the treatment of breast cancer: Initial experience with the EGFR/ErbB-2 inhibitor lapatinib [J].

Burris, HA .

ONCOLOGIST, 2004, 9 :10-15

[7] Acceptorless dehydrogenative synthesis of 2-substituted quinazolines from 2-aminobenzylamine with primary alcohols or aldehydes by heterogeneous Pt catalysts [J].

Chaudhari, Chandan ;

Siddiki, S. M. A. Hakim ;

Tamura, Masazumi ;

Shimizu, Ken-ichi .

RSC ADVANCES, 2014, 4 (95) :53374-53379

[8] A convenient palladium-catalyzed carbonylative synthesis of quinazolines from 2-aminobenzylamine and aryl bromides [J].

Chen, Jianbin ;

Natte, Kishore ;

Neumann, Helfried ;

Wu, Xiao-Feng .

RSC ADVANCES, 2014, 4 (99) :56502-56505

[9] A Novel Ruthenium-Catalyzed Dehydrogenative Synthesis of 2-Arylquinazolines from 2-Aminoaryl Methanols and Benzonitriles [J].

Chen, Mengmeng ;

Zhang, Min ;

Xiong, Biao ;

Tan, Zhenda ;

Lv, Wan ;

Jiang, Huanfeng .

ORGANIC LETTERS, 2014, 16 (22) :6028-6031

[10] Rutaecarpine Analogues Reduce Lipid Accumulation in Adipocytes via Inhibiting Adipogenesis/Lipogenesis with AMPK Activation and UPR Suppression (vol 8, pg 2301, 2013) [J].

Chen, Ying-Chun ;

Zeng, Xiao-Yi ;

He, Yan ;

Liu, Hong ;

Wang, Bin ;

Zhou, Han ;

Chen, Jian-Wen ;

Liu, Pei-Qing ;

Gu, Lian-Quan ;

Ye, Ji-Ming ;

Huang, Zhi-Shu .

ACS CHEMICAL BIOLOGY, 2015, 10 (06) :1570-1571

← 1 2 3 4 5 6 7 8 9 10 →