A Site-Selective C-N Bond Formation of 2,4-Dichloro-5H-pyrano[2,3-d]pyrimidines and Amide

被引:0
|
作者
Qin, Jinjing [1 ]
Li, Zhenhua [1 ]
Cao, Yingyan [1 ]
Xie, Yuanyuan [1 ]
Su, Weike [1 ]
机构
[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Zhejiang, Peoples R China
来源
CHEMISTRYSELECT | 2021年 / 6卷 / 43期
基金
中国国家自然科学基金;
关键词
acetanilide; amination; nucleophilic substitution; pyrano[2; 3-d]pyrimidine; ANTITUMOR-ACTIVITY; DEHYDRATION; DERIVATIVES; PYRIMIDINE; EFFICIENT; DISCOVERY; NITRILES; INSIGHT; ANALOGS; TUMOR;
D O I
10.1002/slct.202102824
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A serious of C-4-position aniline functionalized 5H-pyrano[2,3-d]pyrimidine derivatives were synthesized from the corresponding chlorinated pyrimidines and acetanilides. This process was approached by treating the acetanilide with NaH instead of aniline, where a dissociation of the acyl group in situ happened during the reaction. The strategy worked out the non-reactive route resulted from the low reactivity of aniline. This C-N bond formation features mild reaction conditions, simple execution, and broad substrate scope.
引用
收藏
页码:12032 / 12035
页数:4
相关论文
共 50 条
  • [1] 2H-PYRANO[2,3-D]PYRIMIDINES
    WOODS, LL
    TEXAS JOURNAL OF SCIENCE, 1973, 24 (04): : 543 - 546
  • [2] Convenient selective synthesis of pyrano[2,3-d]pyrimidines
    Yu. M. Litvinov
    A. M. Shestopalov
    Russian Chemical Bulletin, 2008, 57 : 2223 - 2226
  • [3] Convenient selective synthesis of pyrano[2,3-d]pyrimidines
    Litvinov, Yu. M.
    Shestopalov, A. M.
    RUSSIAN CHEMICAL BULLETIN, 2008, 57 (10) : 2223 - 2226
  • [4] One-Pot Cascade Heterocyclization of γ- and β-Ketomalononitriles to 2,4-Dichloro-Substituted Pyrano[2,3-d]pyrimidines and Furo[2,3-d]pyrimidines Mediated by Triphosgene and Triphenylphosphine Oxide
    Li, Zhen-Hua
    Jiang, Zhi-Jiang
    Shao, Qiao-Ling
    Qin, Jin-Jing
    Shu, Qiang-Feng
    Lu, Wen-Hao
    Su, Wei-Ke
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (12): : 6423 - 6431
  • [5] SYNTHESIS OF 4H-PYRANO[2,3-D]PYRIMIDINES
    MARCHALIN, S
    ILAVSKY, D
    BRUNCKO, M
    MONATSHEFTE FUR CHEMIE, 1989, 120 (12): : 1101 - 1105
  • [6] HETEROCYCLIC BETA-ENAMINO ESTERS .53. NOVEL 5,8-DIHYDROPYRIDO-[2,3-D]PYRIMIDINES AND 5H-PYRANO-[2,3-D]PYRIMIDINES
    WAMHOFF, H
    PAASCH, J
    LIEBIGS ANNALEN DER CHEMIE, 1990, (10): : 995 - 999
  • [7] 2,4-DIAMINOTHIENO [2,3-D] PYRIMIDINES AS ANTIFOLATES AND ANTIMALARIALS .2. SYNTHESIS OF 2,4-DIAMINOPYRIDO [4',3' - 4,5] THIENO [2,3-D] PYRIMIDINES AND 2,4-DIAMINO-8H-THIOPYRANO [4',3' - 4,5] THIENO [2,3-D] PYRIMIDINES
    CHAYKOVSKY, M
    LIN, M
    ROSOWSKY, A
    MODEST, EJ
    JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (03) : 188 - 191
  • [8] Palladium-catalysed site-selective arene ortho C-H fluoroalkoxylation of 4-aryl-pyrrolo[2,3-d]pyrimidines
    Jiang, Yunfeng
    Pan, Chenhong
    Tang, Ting
    Liu, Mingrui
    Zhang, Xingxian
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (13) : 2748 - 2753
  • [9] Metal-free site-selective C-N bond-forming reaction of polyhalogenated pyridines and pyrimidines
    Wang, Lei
    Liu, Ning
    Dai, Bin
    RSC ADVANCES, 2015, 5 (100) : 82097 - 82111
  • [10] Ring closure reactions of pyrido[2,3-d]pyrimidines to Pyrano[2′,3′:4,5]- and Oxazolo[5′,4′:4,5]pyrido[2,3-d]pyrimidines
    Van Tinh, Dang
    Stadlbauer, Wolfgang
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (05) : 1359 - 1364