Three-Component Bicyclization Leading to Densely Functionalized Pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidines

被引:8
作者
Hao, Wen-Juan [1 ]
Zhou, Peng [1 ]
Wu, Fei-Yue [1 ]
Jiang, Bo [1 ,2 ]
Tu, Shu-Jiang [1 ]
Li, Guigen [2 ,3 ]
机构
[1] Jiangsu Normal Univ, Sch Chem & Chem Engn, Xuzhou 221116, Jiangsu, Peoples R China
[2] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA
[3] Nanjing Univ, Collaborat Innovat Ctr Chem Life Sci, Inst Chem & BioMed Sci, Nanjing 210093, Jiangsu, Peoples R China
基金
中国国家自然科学基金; 美国国家卫生研究院; 美国国家科学基金会;
关键词
Multicomponent reactions; Microwave chemistry; Cyclization; Polycycles; Fused-ring systems; STEREOSELECTIVE-SYNTHESIS; MULTICOMPONENT REACTIONS; DOMINO REACTION; ACCESS; CONSTRUCTION; RITANSERIN; HETEROANNULATION; CYCLOADDITION; DERIVATIVES; PATHWAYS;
D O I
10.1002/ejoc.201600163
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A three-component bicyclization strategy for the efficient synthesis of densely functionalized pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidines from readily accessible aryl aldehydes, -thiocyanate ketones, and pyrazol-5-amines was established. The reaction pathway involves a nucleophilic addition/5-exo-trig/6-endo-trig bicyclization sequence that results in continuous multiple bond-forming events, including the formation of C-N and C-C bonds, to give high levels of molecular complexity.
引用
收藏
页码:1968 / 1971
页数:4
相关论文
共 48 条
  • [1] Synthesis and pharmacological evaluation of newer thiazolo [3,2-a] pyrimidines for anti-inflammatory and antinociceptive activity
    Alam, Ozair
    Khan, Suroor A.
    Siddiqui, Nadeem
    Ahsan, Waquar
    [J]. MEDICINAL CHEMISTRY RESEARCH, 2010, 19 (09) : 1245 - 1258
  • [2] Back T, 1998, NEUROL RES, V20, P643
  • [3] Simple and quick preparation of α-thiocyanate ketones in hydroalcoholic media. Access to 5-aryl-2-imino-1,3-oxathiolanes
    Bisogno, Fabricio R.
    Cuetos, Anibal
    Lavandera, Ivan
    Gotor, Vicente
    [J]. GREEN CHEMISTRY, 2009, 11 (04) : 452 - 454
  • [4] Catalytic arylsulfonyl radical-triggered 1,5-enyne-bicyclizations and hydrosulfonylation of α,β-conjugates
    Chen, Zhen-Zhen
    Liu, Shuai
    Hao, Wen-Juan
    Xu, Ge
    Wu, Shuo
    Miao, Jiao-Na
    Jiang, Bo
    Wang, Shu-Liang
    Tu, Shu-Jiang
    Li, Guigen
    [J]. CHEMICAL SCIENCE, 2015, 6 (11) : 6654 - 6658
  • [5] A randomized, double-blind, placebo-controlled study of ritanserin pharmacotherapy for cocaine dependence
    Cornish, JW
    Maany, I
    Fudala, PJ
    Ehrman, RN
    Robbins, SJ
    O'Brien, CP
    [J]. DRUG AND ALCOHOL DEPENDENCE, 2001, 61 (02) : 183 - 189
  • [6] Den Boer JA, 2000, HUM PSYCHOPHARM CLIN, V15, P179, DOI 10.1002/(SICI)1099-1077(200004)15:3<179::AID-HUP156>3.0.CO
  • [7] 2-N
  • [8] Chemistry and Biology Of Multicomponent Reactions
    Domling, Alexander
    Wang, Wei
    Wang, Kan
    [J]. CHEMICAL REVIEWS, 2012, 112 (06) : 3083 - 3135
  • [9] El-Din A. S., 2003, SULFUR LETT, V26, P35
  • [10] Novel Double [3+2+1] Heteroannulation for Forming Unprecedented Dipyrazolo-Fused 2,6-Naphthyridines
    Fan, Wei
    Ye, Qin
    Xu, Hai-Wei
    Jiang, Bo
    Wang, Shu-Liang
    Tu, Shu-Jiang
    [J]. ORGANIC LETTERS, 2013, 15 (09) : 2258 - 2261