Base-promoted [4+2] annulation of pyrrole-2-carbaldehyde derivatives with β,γ-unsaturated α-ketoesters: syntheses of 5,6-dihydroindolizines

被引：8
|
作者：
Zhang, You-Ya [1 ]
Li, Lin [1 ]
Ma, Ai-Jun [1 ]
Wang, Wei-Feng [1 ,2 ,3 ]
Peng, Jin-Bao [1 ]
机构：
[1] Wuyi Univ, Sch Biotechnol & Hlth Sci, Jiangmen 529020, Guangdong, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[3] Lanzhou Univ, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 44期
关键词：
D TRIMETHYL ETHER; ONE-POT SYNTHESIS; CATALYZED SYNTHESIS; POLYSUBSTITUTED INDOLIZINES; LAMELLARIN D; CONSTRUCTION; CYCLIZATION; PYRROLE; ACCESS;
D O I：
10.1039/d2ob01903e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A base-promoted [4 + 2] annulation of pyrrole-2-carbaldehyde derivatives with beta,gamma-unsaturated alpha-ketoesters for the syntheses of multisubstituted 5,6-dihydroindolizines was developed. Using DBN as a base, the reaction proceeds smoothly under mild conditions to provide the target products in moderate to high yields, and many useful functional groups can be tolerated.
引用
收藏
页码：8633 / 8637
页数：5
相关论文
共 50 条
  • [1] Oxidative [4+2] Annulation of Pyrrole-2-carbaldehyde Derivatives with o-Hydroxyphenyl Propargylamines: Syntheses of 5,6,7-Trisubstituted Indolizines
    Wang, Yu-Qing
    Chen, Li-Jia
    Yang, Rui-Lin
    Lang, Ming
    Peng, Jin-Bao
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (63)
  • [2] "One-pot" cascade approach to 5,6-dihydroindolizines and indolizines from pyrrole-2-carbaldehydes and nitroethylenes
    Zhong, Wen
    Zhu, Huajian
    Zou, Hongbin
    TETRAHEDRON, 2017, 73 (23) : 3181 - 3187
  • [3] Synthesis of Pyrrole-2-carbaldehyde Derivatives by Oxidative Annulation and Direct Csp3-H to C=O Oxidation
    Wu, Xia
    Zhao, Peng
    Geng, Xiao
    Wang, Can
    Wu, Yan-dong
    Wu, An-xin
    ORGANIC LETTERS, 2018, 20 (03) : 688 - 691
  • [4] Base-Promoted (5+2) Annulation between 2-(Alkynylaryl)acetonitriles and Arylalkynes for the Synthesis of Benzocycloheptene Derivatives
    Li, Jiatian
    Tan, Xiangwen
    Jiang, Huanfeng
    Wu, Wanqing
    ORGANIC LETTERS, 2024, 26 (26) : 5409 - 5414
  • [5] An unnatural hydrophobic base pair with shape complementarity between pyrrole-2-carbaldehyde and 9-methylimidazo[(4,5)-b]pyridine
    Mitsui, T
    Kitamura, A
    Kimoto, M
    To, T
    Sato, A
    Hirao, I
    Yokoyama, S
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (18) : 5298 - 5307
  • [6] Highly enantioselective construction of carbazole derivatives via [4+2] cycloaddition of silyloxyvinylindoles and β,γ-unsaturated α-ketoesters
    Zhao, Xiaohu
    Mei, Hongjiang
    Xiong, Qian
    Fu, Kai
    Lin, Lili
    Liu, Xiaohua
    Feng, Xiaoming
    CHEMICAL COMMUNICATIONS, 2016, 52 (70) : 10692 - 10695
  • [7] Sequential Base-Promoted Formal [4+2] Allenoate Based Cycloaddition: Synthesis of Functionalized Acridines
    Shirazian, Toktam S.
    Tejeneki, Hossein Zahedian
    Nikbakht, Ali
    Rominger, Frank
    Balalaie, Saeed
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (34)
  • [8] Highly Stereoselective [4+2] Cycloaddition of Azlactones to β,γ-Unsaturated α-Ketoesters Catalyzed by an Axially Chiral Guanidine Base
    Terada, Masahiro
    Nii, Hiroyuki
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (06) : 1760 - 1763
  • [9] BASE-PROMOTED REACTIONS OF EPOXIDES .2. 3,4- AND 5,6-EPOXYCYCLOOCTENE
    CRANDALL, JK
    CHANG, LH
    JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (03): : 532 - &
  • [10] Base-Promoted [3+2] Annulation of Carbodiimides with Diazoacetonitrile for Synthesis of 5-Amino-4-cyano-1,2,3-triazoles
    Zhou, Lu-Nan
    Zhang, Fa-Guang
    Cheung, Chi Wai
    Ma, Jun-An
    SYNLETT, 2024, 35 (13) : 1557 - 1560
12345