Synthesis of Indolizines through Oxidative Linkage of C-C and C-N Bonds from 2-Pyridylacetates

被引:44
|
作者
Mohan, Darapaneni Chandra [1 ]
Ravi, Chitrakar [1 ]
Pappula, Venkatanarayana [1 ]
Adimurthy, Subbarayappa [1 ]
机构
[1] CSIR Cent Salt & Marine Chem Res Inst, Acad Sci & Innovat Res, Bhavnagar 364002, Gujarat, India
来源
JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 13期
关键词
ONE-POT; MULTICOMPONENT SYNTHESIS; CYCLIZATION; KETONES; FUNCTIONALIZATION; DERIVATIVES; ANNULATION; ALKYNES; IODINE; 2-ALKYLAZAARENES;
D O I
10.1021/acs.joc.5b00477
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of indolizine-1-carboxylates through the Ortoleva-King reaction of 2-pyridylacetate followed by the Aldol condensation under mild reaction conditions has been described. This protocol is compatible with a broad range of functional groups, and it has been also successfully extended to unsaturated ketones, bringing about the regioselective formation of benzoyl-substituted indolizines through Michael addition followed by C-N bond formation, which are difficult to prepare by previous methods in a single step.
引用
收藏
页码:6846 / 6855
页数:10
相关论文
共 50 条
  • [41] ELASTIC SCATTERING IN N-N, C-N, AND C-C SYSTEMS
    SMITH, AM
    STEIGERT, FE
    PHYSICAL REVIEW, 1962, 125 (03): : 988 - &
  • [42] Cuprous Oxide Catalyzed Oxidative C-C Bond Cleavage for C-N Bond Formation: Synthesis of Cyclic Imides from Ketones and Amines
    Wang, Min
    Lu, Jianmin
    Ma, Jiping
    Zhang, Zhe
    Wang, Feng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) : 14061 - 14065
  • [43] Substrate Directed C-H Activation for the Synthesis of Benzo[c]cinnolines through a Sequential C-C and C-N Bond Formation
    Reddy, B. V. Subba
    Reddy, C. Ravikumar
    Reddy, M. Rajashekhar
    Yarlagadda, Suresh
    Sridhar, B.
    ORGANIC LETTERS, 2015, 17 (15) : 3730 - 3733
  • [44] Samarium(III)-Catalyzed C(sp3)-H Bond Activation: Synthesis of Indolizines via C-C and C-N Coupling between 2-Alkylazaarenes and Propargylic Alcohols
    Wang, Xu
    Li, Shen-yan
    Pan, Ying-ming
    Wang, Heng-shan
    Liang, Hong
    Chen, Zhen-feng
    Qin, Xiao-huan
    ORGANIC LETTERS, 2014, 16 (02) : 580 - 583
  • [45] MAKING C-N BONDS
    Arnaud, Celia
    CHEMICAL & ENGINEERING NEWS, 2014, 92 (05) : 8 - 8
  • [46] Selective cleavage and reconstruction of C-N/C-C bonds in saturated cyclic amines: tunable synthesis of lactams and functionalized acyclic amines
    He, Yan
    Yang, Jintao
    Zhang, Xinying
    Fan, Xuesen
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (18) : 5118 - 5123
  • [47] Catalytic alkynylations through the activation of C-N bonds
    Panda, Biswajit
    ARKIVOC, 2023,
  • [48] Scission of C-C and C-N bonds of quinoline over nitrogen-doped biocarbon anchored (3-Mo2C
    Li, Zhiqin
    Li, Zhuangzhuang
    Qiu, Zegang
    Shi, Yafei
    Chen, Chaoqiu
    Chen, Shuai
    FUEL, 2025, 386
  • [49] Nickel-in-charcoal (Ni/C): An efficient heterogeneous catalyst for the construction of C-C, C-N, and C-H bonds
    Frieman, BA
    Taft, BR
    Lee, CT
    Butler, T
    Lipshutz, BH
    SYNTHESIS-STUTTGART, 2005, (17): : 2989 - 2993
  • [50] Copper catalyzed C-H functionalization: New direct routes to C-N, C-C, and C-O bonds
    Warren, Timothy H.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245