Synthesis of 3-Ethyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one by Novel Palladium(II)-Catalyzed Cyclization and Ring-Closing Metathesis

被引:11
|
作者
Chavan, Subhash P. [1 ]
Pathak, Ashok B. [1 ]
Pawar, Kailash P. [1 ]
机构
[1] Natl Chem Lab, CSIR, Div Organ Chem, Pune 411008, Maharashtra, India
来源
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 07期
关键词
pyrrolinone; glimepiride; antidiabetic; metabolite; lactams; ring-closing metathesis; cyclization; RUTHENIUM CARBENE COMPLEXES; RCM; ISOMERIZATION; DERIVATIVES; PYRROLE; LIGANDS; ROUTE;
D O I
10.1055/s-0034-1379985
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of 3-ethyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one is described starting from commercially available allylamine and 4-methoxybenzylamine employing palladium-catalyzed cyclization or ring-closing metathesis as the key steps.
引用
收藏
页码:955 / 960
页数:6
相关论文
共 50 条
  • [1] Scalable Synthesis of 3-Ethyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one: An Important Building Block of the Antidiabetic Drug Glimepiride
    Chavan, Subhash P.
    Pawar, Ambaji A.
    Patil, Niteen B.
    Kadam, Appasaheb L.
    Shinde, Shrikrishna S.
    SYNTHESIS-STUTTGART, 2020, 52 (22): : 3480 - 3484
  • [2] Photocatalytic Cyclization/Defluorination Domino Sequence to Access 3-Fluoro-1,5-dihydro-2H-pyrrol-2-one Scaffold
    Ye, Zhi-Peng
    Hu, Yuan-Zhuo
    Guan, Jian-Ping
    Chen, Kai
    Liu, Fang
    Gao, Jie
    Xiao, Jun-An
    Xiang, Hao-Yue
    Chen, Xiao-Qing
    Yang, Hua
    ORGANIC LETTERS, 2021, 23 (12) : 4754 - 4758
  • [3] Ring-closing metathesis for the synthesis of 2H- and 4H-chromenes
    van Otterlo, WAL
    Ngidi, EL
    Kuzvidza, S
    Morgans, GL
    Moleele, SS
    de Koning, CB
    TETRAHEDRON, 2005, 61 (42) : 9996 - 10006
  • [4] Synthesis of 2H-1,5-benzodioxepin and 2,5-dihydro-1,6-benzodioxocin derivatives via ring-closing metathesis reaction
    Mamouni, R
    Soukri, M
    Lazar, S
    Akssira, M
    Guillaumet, G
    TETRAHEDRON LETTERS, 2004, 45 (12) : 2631 - 2633
  • [5] Ring-closing metathesis of prochiral oxaenediynes to racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2H-pyrans
    Kolarikova, Viola
    Rybackova, Marketa
    Svoboda, Martin
    Kvicala, Jaroslav
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 2757 - 2768
  • [6] Synthesis of 2H-Chromenes via Hydrazine-Catalyzed Ring-Closing Carbonyl-Olefin Metathesis
    Zhang, Yunfei
    Jermaks, Janis
    MacMillan, Samantha N.
    Lambert, Tristan H.
    ACS CATALYSIS, 2019, 9 (10): : 9259 - 9264
  • [7] Substituted 3(2H)-Furanones by a Tandem Michael Addition/Palladium-Catalyzed Ring-Closing Protocol
    John, Jubi
    Hopf, Henning
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (05) : 841 - 845
  • [8] Synthesis of 2,3,4,7-tetrahydro-1H-azepines as privileged ligand scaffolds for the design of aspartic protease inhibitors via a ring-closing metathesis approach
    Brass, Sascha
    Chan, Nan-Si
    Gerlach, Christof
    Luksch, Torsten
    Boettcher, Jark
    Diederich, Wlibke E.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (24-25) : 5406 - 5422
  • [9] A Novel and Efficient Synthesis of 3-[(4,5-Dihydro-1H-pyrrol-3-yl)carbonyl]-2H-chromen-2-ones (=3-[(4,5-Dihydro-1H-pyrrol-3-yl)carbonyl]-2H-1-benzopyran-2-ones)
    Alizadeh, Abdolali
    Ghanbaripour, Rashid
    HELVETICA CHIMICA ACTA, 2013, 96 (03) : 473 - 477
  • [10] NOVEL AND EFFICIENT CYCLIZATION PROCEDURE FOR THE SYNTHESIS OF 2,5-DISUBSTITUTED-1,3,4-THIADIAZOLES WITHOUT USING ANY RING-CLOSING REAGENTS
    Lin, Qi
    Zhang, You-Ming
    Li, Man-Lin
    Wei, Tai-Bao
    SYNTHETIC COMMUNICATIONS, 2012, 42 (22) : 3251 - 3260