Preparation of pyridopyrazines through tandem Pd-catalyzed C-N/C-C coupling reactions of Ugi adducts

被引：0

作者：

Takallou, Ahmad ^{[1
]}

Al-Siyabi, Munir ^{[1
]}

Al-Shidhani, Sulaiman ^{[1
]}

Lotfi Nosood, Yazdanbakhsh ^{[1
]}

Habibi, Azizollah ^{[2
]}

Almaani, Alhajaj ^{[1
]}

Anwar, Muhammad U. ^{[1
]}

Al-Harrasi, Ahmed ^{[1
]}

机构：

[1] Univ Nizwa, Nat & Med Sci Res Ctr, POB 33, Nizwa 616, Oman

[2] Kharazmi Univ, Fac Chem, Daneshgah Sq,Shahid Beheshti St, Karaj 3197937551, Iran

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 48期

关键词：

TRANSFORMATIONS; HETEROCYCLES; ACTIVATION; ACCESS; METAL;

D O I：

10.1039/d3ob01768k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Pd-catalyzed selective tandem cyclization of the Ugi adduct via Buchwald-Hartwig/C-H bond functionalization reactions has been reported. This sequence offers an interesting approach for synthesizing a wide range of pyrido[1,2-a]pyrazine-3,6-dione scaffolds under mild reaction conditions in moderate to excellent yields. The scope and limitations of the protocol are discussed. Palladium-catalyzed chemo-selective tandem C-N/C-C coupling reactions to prepare pyridopyrazines from Ugi adducts.

引用

页码：9530 / 9533

页数：4

共 29 条

[1]

Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]

[2] Regio- and Chemoselective Formation of Spiroindolinone-Isoindolinone by a Palladium-Catalyzed Buchwald-Hartwig Addition-Elimination Sequence [J].

Butani, Himanshu H. ;

Vachhani, Dipak D. ;

Bhoya, Umed C. ;

Shah, Anamik K. ;

Van der Eycken, Erik V. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (30) :6634-6638

[3] Isocyanide Insertion: De Novo Synthesis of Trifluoromethylated Phenanthridine Derivatives [J].

Cheng, Yuanzheng ;

Jiang, Heng ;

Zhang, Yan ;

Yu, Shouyun .

ORGANIC LETTERS, 2013, 15 (21) :5520-5523

[4] One-pot synthesis of spiropyrroloquinoline-isoindolinone and their aza-analogs via the Ugi-4CR/metal-free intramolecular bis-annulation process [J].

Ghandi, Mehdi ;

Zarezadeh, Nahid ;

Abbasi, Alireza .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (30) :8211-8220

[5] Advances in Base-Mediated Post-Ugi Transformations via Peptidyl Anion Trapping [J].

Ghoshal, Anirban ;

Ambule, Mayur D. ;

Yadav, Anamika ;

Srivastava, Ajay Kumar .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (02) :315-333

[6] Copper-Catalyzed C-H Functionalization Reactions: Efficient Synthesis of Heterocycles [J].

Guo, Xun-Xiang ;

Gu, Da-Wei ;

Wu, Zhengxing ;

Zhang, Wanbin .

CHEMICAL REVIEWS, 2015, 115 (03) :1622-1651

[7] Facile construction of diverse polyheterocyclic scaffolds via gold-catalysed dearomative spirocyclization/1,6-addition cascade [J].

He, Yi ;

Wu, Danjun ;

Li, Zhenghua ;

Robeyns, Koen ;

Van Meervelt, Luc ;

Van der Eycken, Erik V. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (25) :6284-6292

[8] Transition Metal-Catalyzed Tandem Reactions of Ynamides for Divergent N-Heterocycle Synthesis [J].

Hong, Feng-Lin ;

Ye, Long-Wu .

ACCOUNTS OF CHEMICAL RESEARCH, 2020, 53 (09) :2003-2019

[9] A Fast Track to Ind les and Annulated Indoles through ortho- vs ipso-Amination of Aryl Halides [J].

Jafarpour, Farnaz ;

Ghasemi, Mehran ;

Mohaghegh, Farid ;

Asgari, Sara ;

Habibi, Azizollah .

ORGANIC LETTERS, 2019, 21 (24) :10143-10148

[10] Tandem Reaction of Allenoate Formation and Cyclization: Divergent Synthesis of Four- to Six-Membered Heterocycles [J].

Ji, Danqing ;

Liu, Kai ;

Sun, Jiangtao .

ORGANIC LETTERS, 2018, 20 (23) :7708-7711

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