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

[21] Synthesis of Pyrrolidin-5-one-2-carboxamides through Cyclization of N-Substituted-2-alleneamides [J].

Shahriari, Azadeh ;

Amiri, Kamran ;

Nikbakht, Ali ;

Rominger, Frank ;

Bijanzadeh, Hamid Reza ;

Balalaie, Saeed .

JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (12) :7778-7785

[22] Metal-mediated post-Ugi transformations for the construction of diverse heterocyclic scaffolds [J].

Sharma, Upendra K. ;

Sharma, Nandini ;

Vachhani, Dipak D. ;

Van der Eycken, Erik V. .

CHEMICAL SOCIETY REVIEWS, 2015, 44 (07) :1836-1860

[23] Phenanthridine-Fused Tetracyclic Ring System: Metal-Free Diastereoselective Modular Construction of Highly Constrained Polyheterocycles via Post-Ugi Tandem Modification [J].

Singh, Karandeep ;

Malviya, Bhanwar Kumar ;

Jaiswal, Pradeep K. ;

Verma, Ved Prakash ;

Chimni, Swapandeep Singh ;

Sharma, Siddharth .

ORGANIC LETTERS, 2019, 21 (17) :6726-6730

[24] Diversification of Peptidomimetics and Oligopeptides through Microwave-Assisted Rhodium(III)-Catalyzed Intramolecular Annulation [J].

Song, Liangliang ;

Tian, Guilong ;

Blanpain, Anna ;

Van Meervelt, Luc ;

Van der Eyckena, Erik V. .

ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (19) :4442-4447

[25] Post-Ugi Cascade Transformations for Accessing Diverse Chromenopyrrole Collections [J].

Srinivasulu, Vunnam ;

Sieburth, Scott McN. ;

El-Awady, Raafat ;

Kariem, Noor M. ;

Tarazi, Hamadeh ;

O'Connor, Matthew John ;

Al-Tel, Taleb H. .

ORGANIC LETTERS, 2018, 20 (03) :836-839

[26] One-Pot, Base- and Metal-Free Practical Synthesis of Novel Cycloalkene-Fused [1,4]Thiazepines through the Sequential Ugi/SNCsp2 Reactions [J].

Takallou, Ahmad ;

Al-Shidhani, Sulaiman ;

Anwar, Muhammad U. ;

Al-Harrasi, Ahmed .

SYNTHESIS-STUTTGART, 2023, 55 (03) :489-498

[27] Indium(III) Chloride-Catalyzed Isocyanide Insertion Reaction to Construct Complex Spirooxindole [J].

Tian, Yaming ;

Tian, Lumin ;

He, Xiang ;

Li, Chunju ;

Jia, Xueshun ;

Li, Jian .

ORGANIC LETTERS, 2015, 17 (19) :4874-4877

[28]

Xu Z., 2020, CHINESE J CHEM, V38, P307

[29] A Synthesis of Spirooxindole-Isoindolinones Through Ugi Reaction Followed by Copper-Catalyzed Tandem C-N/C-C Coupling Process [J].

Zhong, Xianqiang ;

Luo, Jianghao ;

Zhou, Wei ;

Cai, Qian .

ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (21) :4969-4973

← 1 2 3 →