Pd/PTABS: An Efficient Catalytic System for the Aminocarbonylation of a Sugar-Protected Nucleoside

被引：15

作者：

Bhilare, Shatrughn ^{[1
]}

Shah, Jagrut ^{[1
]}

Gaikwad, Vinayak ^{[1
]}

Gupta, Gaurav ^{[1
]}

Sanghvi, Yogesh S. ^{[2
]}

Bhanage, Bhalchandra M. ^{[1
]}

Kapdi, Anant ^{[1
]}

机构：

[1] Inst Chem Technol, Dept Chem, Nathalal Parekh Rd, Mumbai 400019, Maharashtra, India

[2] Rasayan Inc, 2802 Crystal Ridge Rd, Encinitas, CA 92024 USA

来源：

SYNTHESIS-STUTTGART | 2019年 / 51卷 / 22期

关键词：

palladium; PTABS; aminocarbonylation; nucleoside; sangivamycin; CARBONYLATION REACTIONS; ORGANIC-SYNTHESIS; CARBON-MONOXIDE; DESIGN; PURIFICATION; ENANTIOMERS; CHEMISTRY; LIGANDS; REAGENT; AMINES;

D O I：

10.1055/s-0039-1690190

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient and mild protocol for the aminocarbonylation of a nucleoside is developed by employing palladium/(1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate (Pd/PTABS) as the catalytic system. The developed aminocarbonylation methodology employs CO gas at a relatively low temperature of 60 degrees C and is suitable for a wide range of amines, including (heteroaryl)benzylic, aliphatic acyclic, alicyclic and secondary amines. This protocol is also utilized for the synthesis of a sangivamycin precursor by carrying out the Pd-catalyzed amination and aminocarbonylation simultaneously. The utility of this protocol is further demonstrated by the synthesis of the drugs moclobemide and nikethamide.

引用

页码：4239 / 4248

页数：10

共 54 条

[11] Novel water-soluble phosphatriazenes: versatile ligands for Suzuki-Miyaura, Sonogashira and Heck reactions of nucleosides
Bhilare, Shatrughn
Gayakhe, Vijay
Ardhapure, Ajaykumar V.
Sanghvi, Yogesh S.
Schulzke, Carola
Borozdina, Yulia
Kapdi, Anant R.
[J]. RSC ADVANCES, 2016, 6 (87): : 83820 - 83830
[12] Pd/PTABS: Catalyst for Efficient C-H (Hetero)Arylation of 1,3,4-Oxadiazoles Using Bromo(Hetero)Arenes
Bhujaba, Yuvraj B.
Vadagaonkar, Kamlesh S.
Kapdi, Anant R.
[J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (02) : 289 - 295
[13] Pd Metal Catalysts for Cross-Couplings and Related Reactions in the 21st Century: A Critical Review
Biffis, Andrea
Centomo, Paolo
Del Zotto, Alessandro
Zeccal, Marco
[J]. CHEMICAL REVIEWS, 2018, 118 (04) : 2249 - 2295
[14] Blackburn GM, 2006, NUCLEIC ACIDS IN CHEMISTRY AND BIOLOGY, THIRD EDITION, P1, DOI 10.1039/9781847555380
[15] Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds
Brennfuehrer, Anne
Neumann, Helfried
Beller, Matthias
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) : 4114 - 4133
[16] A phase Ib study to assess the efficacy and safety of vismodegib in combination with ruxolitinib in patients with intermediate- or high-risk myelofibrosis
Couban, Stephen
Benevolo, Giulia
Donnellan, William
Cultrera, Jennifer
Koschmieder, Steffen
Verstovsek, Srdan
Hooper, Gregory
Hertig, Christian
Tandon, Maneesh
Dimier, Natalie
Malhi, Vikram
Passamonti, Francesco
[J]. JOURNAL OF HEMATOLOGY & ONCOLOGY, 2018, 11
[17] Palladium-Catalyzed Cross-Coupling Reactions: A Powerful Tool for the Synthesis of Agrochemicals
Devendar, Ponnam
Qu, Ren-Yu
Kang, Wei-Ming
He, Bo
Yang, Guang-Fu
[J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2018, 66 (34) : 8914 - 8934
[18] NEW URIDINE DERIVATIVES FOR SYSTEMATIC EVOLUTION OF RNA LIGANDS BY EXPONENTIAL ENRICHMENT
DEWEY, TM
MUNDT, AA
CROUCH, GJ
ZYZNIEWSKI, MC
EATON, BE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (32) : 8474 - 8475
[19] Mild Pd-Catalyzed Aminocarbonylation of (Hetero)Aryl Bromides with a Palladacycle Precatalyst
Friis, Stig D.
Skrydstrup, Troels
Buchwald, Stephen L.
[J]. ORGANIC LETTERS, 2014, 16 (16) : 4296 - 4299
[20] Moclobemide - An update of its pharmacological properties and therapeutic use
Fulton, B
Benfield, P
[J]. DRUGS, 1996, 52 (03) : 450 - 474

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