Pd(II)-Catalyzed Synthesis of Furo[2,3-b]pyridines from β-Ketodinitriles and Alkynes via Cyclization and N-H/C Annulation

被引：17

作者：

Rakshit, Amitava ^{[1
]}

Dhara, Hirendra Nath ^{[1
]}

Sahoo, Ashish Kumar ^{[1
]}

Alam, Tipu ^{[1
]}

Patel, Bhisma K. ^{[1
]}

机构：

[1] Indian Inst Technol Guwahati, Dept Chem, North Guwahati 781039, India

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 20期

关键词：

CATALYZED ANNULATION; DISCOVERY; ENAMIDES; CARBOPALLADATION; CONSTRUCTION; DERIVATIVES; ACTIVATION; NITRILES; POTENT; SAR;

D O I：

10.1021/acs.orglett.2c01472

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Pd(II)-catalyzed synthesis of furopyridines has been developed from beta-ketodinitriles and alkynes via an unusual N-H/C annulation. The participation of both the nitrile groups and the concurrent construction of furan and pyridine rings through the formation of C-C, C = C, C-O, C-N, and C = N bonds are the important features. The synthetic applicability is further demonstrated through a series of postsynthetic alterations.

引用

页码：3741 / 3746

页数：6

共 47 条

[1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].

Ackermann, Lutz .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295

[2] Regioselective Synthesis of Fused Furans by Decarboxylative Annulation of α,β-Alkenyl Carboxylic Acid with Cyclic Ketone: Synthesis of Di-Heteroaryl Derivatives [J].

Agasti, Soumitra ;

Pal, Tapas ;

Achar, Tapas Kumar ;

Maiti, Siddhartha ;

Pal, Debasis ;

Mandal, Smita ;

Daud, Kishan ;

Lahiri, Goutam Kumar ;

Maiti, Debabrata .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (32) :11039-11043

[3] Electrophilic cyclization of o-acetoxy- and o-benzyloxyalkynylpyridines:: An easy entry into 2,3-disubstituted furopyridines [J].

Arcadi, A ;

Cacchi, S ;

Di Giuseppe, S ;

Fabrizi, G ;

Marinelli, F .

ORGANIC LETTERS, 2002, 4 (14) :2409-2412

[4] Pd(II)-Catalyzed Synthesis of Alkylidene Phthalides via a Decarbonylative Annulation Reaction [J].

Borthakur, Somadrita ;

Baruah, Swagata ;

Sarma, Bipul ;

Gogoi, Sanjib .

ORGANIC LETTERS, 2019, 21 (08) :2768-2771

[5] Palladium-mediated three-component synthesis of furo[2,3-b]pyridones by one-pot coupling of 3-lodopyridones, alkynes, and organic halides [J].

Bossharth, E ;

Desbordes, P ;

Monteiro, N ;

Balme, G .

ORGANIC LETTERS, 2003, 5 (14) :2441-2444

[6] C-H bond functionalization by dual catalysis: merging of high-valent cobalt and photoredox catalysis [J].

Chakraborty, Priyanka ;

Mandal, Rajib ;

Paira, Soumen ;

Sundararaju, Basker .

CHEMICAL COMMUNICATIONS, 2021, 57 (97) :13075-13083

[7] Palladium-Catalyzed Synthesis of Fluorescent Benzo[4,5]imidazo[1,2-a]pyridines through Annulation Reaction of Benzimidazoles and Alkynyl Bromides with Internal Alkynes [J].

Chen, Xin ;

Sun, Peng ;

Mo, Baichuan ;

Chen, Chunxia ;

Peng, Jinsong .

JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01) :352-366

[8] Synthesis of Imidazoles and Oxazoles via a Palladium-Catalyzed Decarboxylative Addition/Cyclization Reaction Sequence of Aromatic Carboxylic Acids with Functionalized Aliphatic Nitriles [J].

Dai, Ling ;

Yu, Shuling ;

Lv, Ningning ;

Ye, Xuanzeng ;

Shao, Yinlin ;

Chen, Zhongyan ;

Chen, Jiuxi .

ORGANIC LETTERS, 2021, 23 (15) :5664-5668

[9] Furo[2,3-b]pyridine-based cannabinoid-1 receptor inverse agonists: Synthesis and biological evaluation. Part 1 [J].

Debenham, John S. ;

Madsen-Duggan, Christina B. ;

Toupence, Richard B. ;

Walsh, Thomas F. ;

Wang, Junying ;

Tong, Xinchun ;

Kumar, Sanjeev ;

Lao, Julie ;

Fong, Tung M. ;

Xiao, Jing Chen ;

Huang, Cathy R-R. C. ;

Shen, Chun-Pyn ;

Feng, Yue ;

Marsh, Donald J. ;

Stribling, D. Sloan ;

Shearman, Lauren P. ;

Strack, Alison M. ;

Goulet, Mark T. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (04) :1448-1452

[10] Metal-catalyzed reactions of organic nitriles and boronic acids to access diverse functionality [J].

Dhara, Hirendra Nath ;

Rakshit, Amitava ;

Alam, Tipu ;

Patel, Bhisma K. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (21) :4243-4277

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