Palladium-catalyzed methylene C(sp3)-H arylation of the adamantyl scaffold

被引:18
作者
Lao, Ye-Xing [1 ,2 ]
Wu, Jia-Qiang [1 ]
Chen, Yunyun [1 ]
Zhang, Shang-Shi [1 ]
Li, Qingjiang [1 ]
Wang, Honggen [1 ]
机构
[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China
[2] Guangzhou Med Univ, Affiliated Hosp 1, Guangzhou 510230, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H BONDS; ALPHA-AMINO-ACIDS; UNACTIVATED C(SP(3))-H; ACTIVATION; FUNCTIONALIZATION; HYDROXYLATION; DERIVATIVES; INHIBITOR; DIVERSIFICATION; CONSTRUCTION;
D O I
10.1039/c5qo00218d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The adamantyl group is prevalent as a key pharmacophore element in drugs. We describe herein a palladium-catalyzed C-H functionalization logic for the methylene C(sp(3))-H arylation of the adamantyl scaffold with the assistance of an amide group. The resulting arylated adamantyl amide was smoothly converted to an amine, providing facile access to the memantine analog.
引用
收藏
页码:1374 / 1378
页数:5
相关论文
共 81 条
[1]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[2]   Inhibition of dipeptidyl peptidase-4 reduces glycemia, sustains insulin levels, and reduces glucagon levels in type 2 diabetes [J].
Ahrén, B ;
Landin-Olsson, M ;
Jansson, PA ;
Svensson, M ;
Holmes, D ;
Schweizer, A .
JOURNAL OF CLINICAL ENDOCRINOLOGY & METABOLISM, 2004, 89 (05) :2078-2084
[3]   Palladium Nanoparticle-Catalyzed Direct Ethynylation of Aliphatic Carboxylic Acid Derivatives via C(sp3)-H Bond Functionalization [J].
Al-Amin, Mohammad ;
Arisawa, Mitsuhiro ;
Shuto, Satoshi ;
Ano, Yusuke ;
Tobisu, Mamoru ;
Chatani, Naoto .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) :1631-1637
[4]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]
[5]   Discovery and preclinical profile of saxagliptin (BMS-477118): A highly potent, long-acting, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes [J].
Augeri, DJ ;
Robl, JA ;
Betebenner, DA ;
Magnin, DR ;
Khanna, A ;
Robertson, JG ;
Wang, AY ;
Simpkins, LM ;
Taunk, P ;
Huang, Q ;
Han, SP ;
Abboa-Offei, B ;
Cap, M ;
Xin, L ;
Tao, L ;
Tozzo, E ;
Welzel, GE ;
Egan, DM ;
Marcinkeviciene, J ;
Chang, SY ;
Biller, SA ;
Kirby, MS ;
Parker, RA ;
Hamann, LG .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (15) :5025-5037
[6]   A Versatile Tripodal Cu(I) Reagent for C-N Bond Construction via Nitrene-Transfer Chemistry: Catalytic Perspectives and Mechanistic Insights on C-H Aminations/Amidinations and Olefin Aziridinations [J].
Bagchi, Vivek ;
Paraskevopoulou, Patrina ;
Das, Purak ;
Chi, Lingyu ;
Wang, Qiuwen ;
Choudhury, Amitava ;
Mathieson, Jennifer S. ;
Cronin, Leroy ;
Pardue, Daniel B. ;
Cundari, Thomas R. ;
Mitrikas, George ;
Sanakis, Yiannis ;
Stavropoulos, Pericles .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (32) :11362-11381
[7]   Novel 2,4-methanoadamantane-benzazepine by domino photochemistry of N-(1-adamantyl)phthalimide [J].
Basaric, Nikola ;
Horvat, Margareta ;
Mlinaric-Majerski, Kata ;
Zimmermann, Elmar ;
Neudoerfl, Joerg ;
Griesbeck, Axel G. .
ORGANIC LETTERS, 2008, 10 (18) :3965-3968
[8]   A Polycomponent Metal-Catalyzed Aliphatic, Allylic, and Benzylic Fluorination [J].
Bloom, Steven ;
Pitts, Cody Ross ;
Miller, David Curtin ;
Haselton, Nathan ;
Holl, Maxwell Gargiulo ;
Urheim, Ellen ;
Lectka, Thomas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (42) :10580-10583
[9]   Oxaziridine-mediated catalytic hydroxylation of unactivated 3° C-H bonds using hydrogen peroxide [J].
Brodsky, BH ;
Du Bois, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (44) :15391-15393
[10]   Enantioselective glyoxylate-ene reactions catalysed by (salen)chromium(III) complexes [J].
Chaladaj, Wojciech ;
Kwiatkowski, Piotr ;
Majer, Jakub ;
Jurczak, Janusz .
TETRAHEDRON LETTERS, 2007, 48 (13) :2405-2408