KI-mediated three-component annelation for the regioselective synthesis of angular azolo[1,5-a]pyrimidine derivatives

被引：0
|
作者：
Guo, Yimei [1 ]
Sun, Zhenhua [1 ]
He, Xiaodan [2 ]
Cao, Penghui [1 ]
Fan, Guangping [1 ]
Gao, Qinghe [1 ]
机构：
[1] Xinxiang Med Univ, Sch Pharm, Xinxiang 453003, Henan, Peoples R China
[2] Xinxiang Med Univ, Affiliated Hosp 2, Xinxiang 453002, Henan, Peoples R China
来源：
NEW JOURNAL OF CHEMISTRY | 2023年 / 47卷 / 40期
关键词：
PHENYL AMIDES; ANTIPROLIFERATIVE AGENTS; PARALLEL SYNTHESIS;
D O I：
10.1039/d3nj03930g
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Herein, a straightforward and regioselective avenue to angular azolo[1,5-a]pyrimidine derivatives via the three-component cyclization of aldehydes and alpha-aminoazoles with cycloketones is presented. The initiation of the condensation reaction between aldehydes and amines is key to the achievement of high regioselectivity in this process through bypassing the general aldol condensation of aldehydes and ketones. It is worth noting that this simple and scalable protocol was successfully applied to the derivatization of several structurally diverse natural products and pharmaceuticals.
引用
收藏
页码：18618 / 18622
页数：5
相关论文
共 50 条
  • [1] NITRO-DERIVATIVES OF AZOLO[1,5-A]PYRIMIDINE - SYNTHESIS AND ANTIVIRAL ACTION
    PILICHEVA, TL
    RUSINOV, VL
    EGOROVA, LG
    CHUPAKHIN, ON
    VLADYKO, GV
    KOROBCHENKO, LV
    BOREKO, EI
    [J]. KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1990, 24 (01): : 41 - 42
  • [2] NITRILES IN HETEROCYCLIC SYNTHESIS - A SINGLE-STEP SYNTHESIS OF AZOLO[1,5-A]PYRIMIDINE AND BENZIMIDAZOLO[1,5-A] PYRIDINE-DERIVATIVES
    KANDEEL, ZE
    [J]. JOURNAL OF CHEMICAL RESEARCH-S, 1995, (07): : 290 - 291
  • [3] Three-component regioselective synthesis and antibacterial evaluation of new arene-linked bis(pyrazolo[1,5-a]pyrimidine) hybrids
    Sanad, Sherif M. H.
    Mekky, Ahmed E. M.
    [J]. SYNTHETIC COMMUNICATIONS, 2023, 53 (09) : 658 - 672
  • [4] Regioselective one-pot three-component synthesis of quinoline based 1,2,4-triazolo[1,5-a]quinoline derivatives
    Ladani, Gaurav G.
    Patel, Manish P.
    [J]. RSC ADVANCES, 2015, 5 (94): : 76943 - 76948
  • [5] The synthesis of new pyrazolo[1,5-a]pyrimidine derivatives
    Marjani, Ahmad Poursattar
    Khalafy, Jabbar
    Salami, Fatemeh
    Ezzati, Mahnaz
    [J]. ARKIVOC, 2015, : 277 - 286
  • [6] Synthesis of functionalized triazolo[1,5-a]pyrimidine derivatives
    Natal’ya V. Chechina
    Nadezhda N. Kolos
    Irina V. Omelchenko
    Vladimir I. Musatov
    [J]. Chemistry of Heterocyclic Compounds, 2018, 54 : 58 - 62
  • [7] Synthesis of functionalized triazolo[1,5-a]pyrimidine derivatives
    Chechina, Natal'ya V.
    Kolos, Nadezhda N.
    Omelchenko, Irina V.
    Musatov, Vladimir I.
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2018, 54 (01) : 58 - 62
  • [8] Three-component synthesis of arene-linked pyrazolo[1,5-a]pyrimidines
    Ahmed, Ahmed A. M.
    Mekky, Ahmed E. M.
    Sanad, Sherif M. H.
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2023, 60 (10) : 1815 - 1821
  • [9] Synthesis of some new purine-related compounds: Regioselective one-pot synthesis of new tetrazolo[1,5-a]pyrimidine, pyrazolo[1,5-a]pyrimidine and pyrimido[1,6-a]pyrimidine derivatives
    Hussein, Ahmed M.
    [J]. JOURNAL OF SAUDI CHEMICAL SOCIETY, 2010, 14 (01) : 61 - 68
  • [10] Synthesis of new sulfapyrimidine and pyrazolo[1,5-a]pyrimidine derivatives
    Ahmed, Ebtsam A. A.
    Elgemeie, Galal H. H.
    Azzam, Rasha A. A.
    [J]. SYNTHETIC COMMUNICATIONS, 2023, 53 (05) : 386 - 401
12345