Di-tert-butyl peroxide as an effective two-carbon unit in oxidative radical cyclization toward 7-methylazolo[1,5-a]pyrimidines

被引：6
作者：
Gao, Qinghe [1 ]
Sun, Zhenhua [1 ]
Wu, Manman [1 ]
Guo, Yimei [1 ]
Han, Xinya [2 ]
Yan, Jufen [2 ]
Ha, Minh Ngoc [3 ]
Quynh Mai Le [4 ]
Xu, Yongtao [5 ]
机构：
[1] Xinxiang Med Univ, Sch Pharm, Xinxiang 453003, Henan, Peoples R China
[2] Anhui Univ Technol, Sch Chem & Chem Engn, Maanshan 243002, Anhui, Peoples R China
[3] Vietnam Natl Univ, Univ Sci, Fac Chem, VNU Key Lab Adv Mat Green Growth, Hanoi 100000, Vietnam
[4] Vietnam Natl Univ, Univ Sci, Fac Biol, Dept Plant Sci, Hanoi 100000, Vietnam
[5] Xinxiang Med Univ, Sch Med Engn, Henan Int Joint Lab Neural Informat Anal & Drug I, Xinxiang 453003, Henan, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 11期
基金：
中国国家自然科学基金;
关键词：
C-H METHYLATION; CASCADE METHYLATION/CYCLIZATION; DICUMYL PEROXIDE; AMIDES; QUINOXALIN-2(1H)-ONES; ARYLACRYLAMIDES; ANNULATION; REAGENT; KETONES; POTENT;
D O I：
10.1039/d2qo00381c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An unexpected oxidative radical cyclization of 3(5)-aminoazoles and aromatic aldehydes with di-tert-butyl peroxide (DTBP) is described. This established protocol enables the assembly of privileged 7-methylpyrazolo[1,5-a]pyrimidines as well as 7-methyl-[1,2,4]triazolo[1,5-a]pyrimidines with excellent regioselectivity and functional group tolerance, where DTBP firstly emerges as the C2 cyclic unit rather than the usual methyl radical source. The reaction is further highlighted by the late-stage modifications of natural products and pharmaceuticals.
引用
收藏
页码：3050 / 3056
页数：7
相关论文
共 57 条
  • [11] Copper(I)-Catalyzed Synthesis of 4,5-Dihydropyrazolo[1,5-a]pyrimidines via Cascade Transformation of N-Propargylic Sulfonylhydrazones with Sulfonyl Azides
    Ding, Zong-Cang
    An, Xiao-Ming
    Zeng, Jia-Hao
    Tang, Zhao-Ning
    Zhan, Zhuang-Ping
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (19) : 3319 - 3324
  • [12] Open-Air Dual-Diamination of Aromatic Aldehydes: Direct Synthesis of Azolo-Fused 1,3,5-Triazines Facilitated by Ammonium Iodide
    Gao, Qinghe
    Wu, Manman
    Zhang, Le
    Xu, Pengju
    Wang, He
    Sun, Zhenhua
    Fang, Lizhen
    Duan, Yingchao
    Bai, Suping
    Zhou, Xiangyu
    Han, Mingxin
    Zhang, Jixia
    Lv, Jieli
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23) : 17265 - 17273
  • [13] Vinylation of α-Aminoazoles with Triethylamine: A General Strategy to Construct Azolo[1,5-a]pyrimidines with a Nonsubstituted Ethylidene Fragment
    Gao, Qinghe
    Sun, Zhenhua
    Xia, Qinfei
    Li, Ruonan
    Wang, Wenlong
    Ma, Siwei
    Chai, Yixin
    Wu, Manman
    Hu, Wei
    Abranyi-Balogh, Peter
    Keseru, Gyorgy M.
    Han, Xinya
    [J]. ORGANIC LETTERS, 2021, 23 (07) : 2664 - 2669
  • [14] Aerobic α,β-C(sp3)-H Bond Difunctionalization and C-N Bond Cleavage of Triethylamine: Difunctional Ammonium Iodide Enabling the Regioselective Synthesis of 4-Arylpyrimido[1,2-b]indazoles
    Gao, Qinghe
    Han, Xinya
    Tong, Peiyuan
    Zhang, Zhiang
    Shen, Haotian
    Guo, Yanrong
    Bai, Suping
    [J]. ORGANIC LETTERS, 2019, 21 (15) : 6074 - 6078
  • [15] Iron-promoted free radical cascade difunctionalization of unsaturated benzamides with silanes
    Ge, Yaxin
    Tian, Yunfei
    Wu, Jilai
    Yan, Qinqin
    Zheng, Luping
    Ren, Yingming
    Zhao, Jincan
    Li, Zejiang
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (83) : 12656 - 12659
  • [16] Pyrazolo[1,5-a]pyrimidines.: Identification of the privileged structure and combinatorial synthesis of 3-(hetero)arylpyrazolo[1,5-a]pyrimidine-6-carboxamides
    Gregg, Brian T.
    Tymoshenko, Dmytro O.
    Razzano, Dana A.
    Johnson, Matthew R.
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2007, 9 (03): : 507 - 512
  • [17] Rhodium(III)-Catalyzed imidoyl C-H Activation for Annulations to Azolopyrimidines
    Halskov, Kim Soholm
    Witten, Michael R.
    Hoang, Gia L.
    Mercado, Brandon Q.
    Ellman, Jonathan A.
    [J]. ORGANIC LETTERS, 2018, 20 (08) : 2464 - 2467
  • [18] Three-Component Coupling of Aldehydes, Aminopyrazoles, and Sulfoxonium Ylides via Rhodium(III)-Catalyzed Imidoyl C-H Activation: Synthesis of Pyrazolo[1,5-a]pyrimidines
    Hoang, Gia L.
    Streit, Andrew D.
    Ellman, Jonathan A.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (24) : 15347 - 15360
  • [19] Synthesis and Structure-Activity Relationship (SAR) of (5,7-Disubstituted 3-phenylsulfonyl-pyrazolo[1,5-a]pyrimidin-2-yl)-methylamines as Potent Serotonin 5-HT6 Receptor (5-HT6R) Antagonists
    Ivachtchenko, Alexandre V.
    Golovina, Elena S.
    Kadieva, Madina G.
    Kysil, Volodymyr M.
    Mitkin, Oleg D.
    Tkachenko, Sergey E.
    Okun, Ilya M.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (23) : 8161 - 8173
  • [20] Peroxide-mediated site-specific C-H methylation of imidazo[1,2-a]pyridines and quinoxalin-2(1H)-ones under metal-free conditions
    Jin, Shengzhou
    Yao, Hua
    Lin, Sen
    You, Xiaoqing
    Yang, Yao
    Yan, Zhaohua
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (02) : 205 - 210
123456