Copper-Catalyzed [4+1] and [4+2] Reactions through Tandem Remote Propargylation/Cyclization/Isomerization with an Amine or a Hydrazine

被引:3
作者
Sun, Yu-Ze [1 ,2 ,3 ]
Lin, Guo-Qiang [1 ,2 ]
He, Zhi-Tao [3 ,4 ,5 ]
机构
[1] Shanghai Normal Univ, Dept Chem, Shanghai 200234, Peoples R China
[2] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Chem Biol, Shanghai 200032, Peoples R China
[3] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[4] Univ Chinese Acad Sci, Hangzhou Inst Adv Study, Sch Chem & Mat Sci, Hangzhou 310024, Peoples R China
[5] Ningbo Zhongke Creat Ctr New Mat, Ningbo 315899, Peoples R China
关键词
copper catalysis; propargylic substitution; 4+1] cyclization; 4+2] cyclization; arylhydrazines; amines; PROPARGYLIC SUBSTITUTION-REACTIONS; ENANTIOSELECTIVE PROPARGYLATION; POTENT; ESTERS; CYCLOADDITION; CONSTRUCTION; HETEROCYCLES; ANNULATION; INHIBITORS; DISCOVERY;
D O I
10.1055/a-2294-5395
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two novel copper-catalyzed cyclization reactions involvinga remote propargylic substitution/cyclization/isomerization cascade aredisclosed. Derivatives of the seldomly studied heterocycles thieno[2,3-c]pyrrole and thieno[2,3-d]pyridazine are conveniently synthesized inmoderate to good yields from primary amines or arylhydrazinesthrough [4+1] and [4+2] reactions, respectively. Preliminary mechanis-tic experiments corroborated the occurrence of the designed cascadereactions
引用
收藏
页码:82 / 86
页数:5
相关论文
共 61 条
[1]   Synthetic Strategies to Access Heteroatomic Spirocentres Embedded in Natural Products [J].
Badart, Michael P. ;
Hawkins, Bill C. .
SYNTHESIS-STUTTGART, 2021, 53 (10) :1683-1705
[2]   Synthesis and properties of thienopyrrole based heteroacenes - indolodibenzothienopyrrole and dicarbazolodithienopyrrole [J].
Balaji, Ganapathy ;
Della Pelle, Andrea M. ;
Popere, Bhooshan C. ;
Chandrasekaran, A. ;
Thayumanavan, S. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (17) :3455-3462
[3]   Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine [J].
Blair, JB ;
Marona-Lewicka, D ;
Kanthasamy, A ;
Lucaites, VL ;
Nelson, DL ;
Nichols, DE .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (06) :1106-1111
[4]  
ccdc, CCDC 2334156 CONTAIN
[5]  
Dal Piaz V, 1998, EUR J MED CHEM, V33, P789
[6]   Novel heterocyclic-fused pyridazinones as potent and selective phosphodiesterase IV inhibitors [J].
DalPiaz, V ;
Giovannoni, MP ;
Castellana, C ;
Palacios, JM ;
Beleta, J ;
Domenech, T ;
Segarra, V .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (10) :1417-1421
[7]   Enantioselective copper-catalyzed propargylic amination [J].
Detz, Remko J. ;
Delville, Marielle M. E. ;
Hiemstra, Henk ;
van Maarseveen, Jan H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (20) :3777-3780
[8]   Copper-Catalyzed Enantioselective Construction of Tertiary Propargylic Sulfones [J].
Enrique Gomez, Jose ;
Cristofol, Alex ;
Kleij, Arjan W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (12) :3903-3907
[9]   Copper-Catalyzed Synthesis of -Amino Acids Featuring Quaternary Stereocenters [J].
Enrique Gomez, Jose ;
Guo, Wusheng ;
Gaspa, Silvia ;
Kleij, Arjan W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (47) :15035-15038
[10]   Recent developments and perspectives in the copper-catalyzed multicomponent synthesis of heterocycles [J].
Fairoosa, Jaleel ;
Neetha, Mohan ;
Anilkumar, Gopinathan .
RSC ADVANCES, 2021, 11 (06) :3452-3469