New synthesis of 3,3-disubstituted piperidin-2-ones from esters and 1-(3-halopropyl)-2,5-dimethylpyrroles

被引：0
|
作者：
V. D. Gvozdev
K. N. Shavrin
O. M. Nefedov
机构：
[1] Russian Academy of Sciences,N. D. Zelinsky Institute of Organic Chemistry
来源：
Russian Chemical Bulletin | 2019年 / 68卷
关键词：
piperidin-2-ones; esters; alkylation; protection groups; 2,5-dimethylpyrrole protection; cyclization;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
3,3-Disubstituted piperidin-2-ones were obtained by alkylation of carboxylic acid esters with 1-(3-halopropyl)-2,5-dimethylpyrroles using lithium diisopropylamide as a base followed by the removal of 2,5-dimethylpyrrole protection and intramolecular cyclization. The overall yields of the target products amounted to 78% in two synthetic steps.
引用
收藏
页码：2108 / 2113
页数：5
相关论文
共 50 条
  • [31] Facile synthesis of 3-substituted and 1,3-disubstituted quinolin-2(1H)-ones from 2-nitrobenzaldehydes
    Park, KK
    Jung, JY
    HETEROCYCLES, 2005, 65 (09) : 2095 - 2105
  • [32] NITROALKENE [4+2] CYCLOADDITION AS A GENERAL AND STEREOSELECTIVE ROUTE TO THE SYNTHESIS OF 3,3-DISUBSTITUTED AND 3,4-DISUBSTITUTED PYRROLIDINES
    DENMARK, SE
    MARCIN, LR
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15): : 3857 - 3868
  • [33] SYNTHESIS AND ANTIBACTERIAL ACTIVITY STUDIES OF 2, 3-DISUBSTITUTED QUINAZOLINONES-4(3H)-ONES
    Arava, Glory
    Naidu, N. Venkatasubba
    HETEROCYCLIC LETTERS, 2015, 5 (03): : 329 - 334
  • [34] NEW, FACILE SYNTHESIS OF 3,3-DISUBSTITUTED PHTHALIDES BASED ON THE REACTION OF α-SUBSTITUTED 2-LITHIOSTYRENES WITH CARBON DIOXIDE
    Kobayashi, Kazuhiro
    Kozuki, Taketoshi
    Fukamachi, Shuhei
    Konishi, Hisatoshi
    HETEROCYCLES, 2010, 81 (01) : 163 - 169
  • [35] Metal-Free Tandem Rearrangement/Lactonization: Access to 3,3-Disubstituted Benzofuran-2-(3H)-ones
    Santi, Micol
    Ould, Darren M. C.
    Wenz, Jan
    Soltani, Yashar
    Melen, Rebecca L.
    Wirth, Thomas
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (23) : 7861 - 7865
  • [36] THE S(N)2 REACTIVITY OF 3,3-DISUBSTITUTED 1,2-DIOXETANES WITH MORPHOLINE
    ADAM, W
    STOSSEL, R
    TREIBER, A
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09): : 2879 - 2884
  • [37] THERMAL-ISOMERIZATION OF 3,3-DISUBSTITUTED 2,2-DIHALO-1-METHYLENECYCLOPROPANES
    MOLCHANOV, AP
    KOSTIKOV, RR
    ZHURNAL ORGANICHESKOI KHIMII, 1988, 24 (05): : 949 - 955
  • [38] The SN2 Reactivity of 3,3-Disubstituted 1,2-Dioxetanes with Morpholine
    Adam, W.
    Stoessel, R.
    Treiber, A.
    Journal of Information Technology, 1995, 10 (01)
  • [39] Reactions of 1-(3,3-Diethoxypropyl)urea with Phenols: Synthesis of 1,6-Disubstituted Tetrahydropyrimidine-2(1H)-ones
    Smolobochkin, Andrey, V
    Gazizov, Almir S.
    Voronina, Julia K.
    Strelnik, Anna G.
    Rizbayeva, Tanzilya S.
    Burilov, Alexander R.
    Pudovik, Michail A.
    CHEMISTRYSELECT, 2019, 4 (37): : 11038 - 11042
  • [40] Copper(I)-catalyzed synthesis of 3,3-disubstituted isoindolin-1-ones from enamides via cascade radical addition and cyclization
    Yu, Hui
    Xuan, Pengfei
    Lin, Jingbo
    Jiao, Mingdong
    TETRAHEDRON LETTERS, 2018, 59 (40) : 3636 - 3641
12345