Base-Promoted Synthesis of 3-Alkenyl-2-pyridones from N-Propargyl-β-enaminones and Aryl Aldehydes

被引：9

作者：

Tian, Qingyu ^{[1
]}

Xiao, Shangyun ^{[1
]}

Cheng, Guolin ^{[1
]}

机构：

[1] Huaqiao Univ, Coll Mat Sci & Engn, Instrumental Anal Ctr, Xiamen Key Lab Optoelect Mat & Adv Mfg, Xiamen 361021, Fujian, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2021年 / 39卷 / 10期

关键词：

Domino reactions; Aldehydes; Alkenes; Enaminone; Pyridones; CATALYZED 2+2+2 CYCLOADDITION; 3,4,6-TRISUBSTITUTED 2-PYRIDONE; BOND-CLEAVAGE; DERIVATIVES; EFFICIENT; CHROMONES;

D O I：

10.1002/cjoc.202100331

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Main observation and conclusion In this article, we report a base-promoted sequential cyclization/aldol-type condensation/isomerization cascade reaction of N-propargyl-beta-enaminones with aryl aldehydes. The key step in this protocol is the generation of 1,4-oxazepine anions from N-propargyl-beta-enaminones under basic conditions, which are captured by aryl aldehydes. The method allows the formation of one pyridone core and one C-C double bond in "one pot", and the preparation of a variety of densely decorated pyridone derivatives in moderate to good yields with broad functional group tolerance.

引用

页码：2781 / 2788

页数：8

共 56 条

[1] Ruthenium-Catalyzed Oxidative Synthesis of 2-Pyridones through C-H/N-H Bond Functionalizations [J].

Ackermann, Lutz ;

Lygin, Alexander V. ;

Hofmann, Nora .

ORGANIC LETTERS, 2011, 13 (12) :3278-3281

[2] [2+2+2] Cyclotrimerization of Alkynes and Isocyanates/Isothiocyanates Catalyzed by Ruthenium-Alkylidene Complexes [J].

Alvarez, Silvia ;

Medina, Sandra ;

Dominguez, Gema ;

Perez-Castells, Javier .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (19) :9995-10001

[3] Domino Reaction Sequence for the Synthesis of [2.2.2]Diazabicycloalkenes and Base-Promoted Cycloreversion to 2-Pyridone Alkaloids [J].

Angello, Nicholas H. ;

Wiley, Robert E. ;

Elmore, Tristan G. ;

Perry, Ryan S. ;

Scheerer, Jonathan R. .

ORGANIC LETTERS, 2018, 20 (17) :5203-5207

[4] Double-Stereodifferentiation in Rhodium-Catalyzed [2+2+2] Cycloaddition: Chiral Ligand/Chiral Counterion Matched Pair [J].

Auge, Mylene ;

Feraldi-Xypolia, Alexandra ;

Barbazanges, Marion ;

Aubert, Corinne ;

Fensterbank, Louis ;

Gandon, Vincent ;

Kolodziej, Emilie ;

Ollivier, Cyril .

ORGANIC LETTERS, 2015, 17 (15) :3754-3757

[5] Copper-Catalyzed Three-Component Cascade Michael Addition/Heck-Type Alkylation/Annulation: Accessing Fully Substituted 1,3-Dihydro-2H-pyrrol-2-ones [J].

Ba, Dan ;

Chen, Yanhui ;

Lv, Weiwei ;

Wen, Si ;

Cheng, Guolin .

ORGANIC LETTERS, 2019, 21 (21) :8603-8606

[6] Construction of Fully Substituted 2-Pyridone Derivatives via Four-Component Branched Domino Reaction Utilizing Microwave Irradiation [J].

Bai, Hairui ;

Sun, Rongrong ;

Liu, Shitao ;

Yang, Lijuan ;

Chen, Xuebing ;

Huang, Chao .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (20) :12535-12548

[7] Iterative Catalysis in the Biosynthesis of Mitochondrial Complex II Inhibitors Harzianopyridone and Atpenin B [J].

Bat-Erdene, Undramaa ;

Kanayama, Daiki ;

Tan, Dan ;

Turner, William C. ;

Houk, K. N. ;

Ohashi, Masao ;

Tang, Yi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (19) :8550-8554

[8] Transition Metal-Catalysed Direct C-H Bond Functionalizations of 2-Pyridone Beyond C3-Selectivity [J].

Biswas, Aniruddha ;

Maity, Saurabh ;

Pan, Subarna ;

Samanta, Rajarshi .

CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (14) :2092-2109

[9] Ligand Effects and Kinetic Investigations of Sterically Accessible 2-Pyridonate Tantalum Complexes for Hydroaminoalkylation [J].

Brandt, Jason W. ;

Chong, Eugene ;

Schafer, Laurel L. .

ACS CATALYSIS, 2017, 7 (09) :6323-6330

[10] Base-promoted ring-closing carbonyl-allene metathesis for the synthesis of 2,4-disubstituted pyrroles [J].

Cheng, Guolin ;

Lv, Weiwei ;

Xue, Lulu .

GREEN CHEMISTRY, 2018, 20 (19) :4414-4417

← 1 2 3 4 5 6 →