Direct Formation of C-C, C-N, and C-O Bonds in Dihydroquinazolines via Hypervalent Iodine(III)-Mediated sp3 C-H Functionalization

被引：4

作者：

Carlson, Haley M. ^{[1
]}

Smith, Sydney R. ^{[1
]}

Mosey, R. Adam ^{[1
]}

机构：

[1] Lake Super State Univ, Sault Sainte Marie, MI 49783 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 02期

关键词：

REISSERT COMPOUND; COUPLING REACTION; CROSS; ALKYLATION; AMIDATION; DISCOVERY; ARYLATION; ACCESS; ETHERS;

D O I：

10.1021/acs.joc.3c02334

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A hypervalent iodine(III)-mediated cross-dehydrogenative coupling reaction for the direct formation of C-C, C-N, and C-O bonds in dihydroquinazolines has been developed. This one-pot method allows for the synthesis of C4-disubstituted dihydroquinazolines as well as C4-spirolactam, spirolactone, and spiroindene dihydroquinazolines in moderate to high yields.

引用

页码：1160 / 1174

页数：15

共 38 条

[1] Substituted quinazolines, part 3. Synthesis, in vitro antitumor activity and molecular modeling study of certain 2-thieno-4(3H)-quinazolinone analogs [J].

Al-Obaid, Abdulrahman M. ;

Abdel-Hamide, Sami G. ;

El-Kashef, Hassan A. ;

Abdel-Aziz, Alaa A. -M. ;

El-Azab, Adel S. ;

Al-Khamees, Hamad A. ;

El-Subbagh, Hussein I. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (06) :2379-2391

[2]

Al-Thebeiti MS, 1998, B POL ACAD SCI-CHEM, V46, P353

[3] One-Pot Tandem Assembly of Amides, Amines, and Ketones: Synthesis of C4-Quaternary 3,4-and 1,4-Dihydroquinazolines [J].

Campbell, Molly, V ;

Iretskii, Alexei, V ;

Mosey, R. Adam .

JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (17) :11211-11225

[4] Synthesis of N-substituted indole derivatives via PIFA-mediated intramolecular cyclization [J].

Du, Yunfei ;

Liu, Renhe ;

Linn, Gregory ;

Zhao, Kang .

ORGANIC LETTERS, 2006, 8 (26) :5919-5922

[5] Dihydroquinazolines enhance 20S proteasome activity and induce degradation of α -synuclein, an intrinsically disordered protein associated with neurodegeneration [J].

Fiolek, Taylor J. ;

Magyar, Christina L. ;

Wall, Tyler J. ;

Davies, Steven B. ;

Campbell, Molly, V ;

Savich, Christopher J. ;

Tepe, Jetze J. ;

Mosey, R. Adam .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2021, 36

[6] The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations [J].

Girard, Simon A. ;

Knauber, Thomas ;

Li, Chao-Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) :74-100

[7] The Novel Anticytomegalovirus Compound AIC246 (Letermovir) Inhibits Human Cytomegalovirus Replication through a Specific Antiviral Mechanism That Involves the Viral Terminase [J].

Goldner, Thomas ;

Hewlett, Guy ;

Ettischer, Nicole ;

Ruebsamen-Schaeff, Helga ;

Zimmermann, Holger ;

Lischka, Peter .

JOURNAL OF VIROLOGY, 2011, 85 (20) :10884-10893

[8]

HIGASHINO T, 1985, CHEM PHARM BULL, V33, P950

[9]

HIGASHINO T, 1988, CHEM PHARM BULL, V36, P930

[10] En Route to Intermolecular Cross-Dehydrogenative Coupling Reactions [J].

Huang, Chia-Yu ;

Kang, Hyotaik ;

Li, Jianbin ;

Li, Chao-Jun .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (20) :12705-12721

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