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
美国国家科学基金会; 美国国家卫生研究院; 中国国家自然科学基金;
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 50 条
  • [1] Multi-component Preparation of Pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidines Using Solvent-free and HSBM Techniques
    Roudbaraki, Seyyed Jalal
    Ziyaadini, Morteza
    Ghashang, Majid
    LETTERS IN ORGANIC CHEMISTRY, 2020, 17 (07) : 512 - 516
  • [2] Three-component [3+2+1] cyclizations leading to densely functionalized benzo[4,5]thiazolo[1,2-a]pyrimidines
    Sao, Ming
    Jiang, Bo
    Wang, Haiying
    Li, Liang
    TETRAHEDRON, 2016, 72 (07) : 1011 - 1017
  • [3] Ionic-liquid Promoted Multi-component Preparation of Pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidines under Solvent-free Conditions
    Ziyaadini, Morteza
    Roudbaraki, Seyyed Jalal
    Ghashang, Majid
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2020, 52 (04) : 311 - 318
  • [4] SYNTHESIS OF PYRAZOLO[3,4-D]PYRIMIDINES AND ISOXAZOLO[3,4-D]PYRIMIDINES
    DAS, PK
    BEHERA, GB
    SAHAY, AK
    MISHRA, BK
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1985, 24 (04): : 437 - 439
  • [5] SYNTHESIS AND PROPERTIES OF THIAZOLO(3,2-A)PYRIMIDINES AND THIAZOLO(3,2-A)PYRROLO(2,3-D)PYRIMIDINES
    BORMANN, G
    TROXLER, F
    HELVETICA CHIMICA ACTA, 1971, 54 (06) : 1687 - &
  • [6] Synthesis of pyrrolino[3,4-d]pyrazoles, pyrazoles, pyrazolo[5,4-d]pyrimidines and pyrazolo[3,4-d]pyrimidines
    Riheem, Nadia A. Abdel
    Rateb, Nora M.
    Eldin, Sanaa M.
    DRUGS OF THE FUTURE, 2007, 32 : 40 - 41
  • [7] SYNTHESIS OF FUNCTIONALIZED PYRAZOLES AND PYRAZOLO[3,4-D]PYRIMIDINES AS POTENTIAL LEISHMANICIDES
    RAM, VJ
    HAQUE, N
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1995, 34 (06): : 521 - 524
  • [8] Synthesis and biological activity of pyrazolo[3,4-d] thiazolo[3,2-a]pyrimidin-4-one derivatives: in silico approach
    Khobragade, Chandrahas N.
    Bodade, Ragini G.
    Dawane, Bhaskar S.
    Konda, Shankaraiah G.
    Khandare, Namdev T.
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2010, 25 (05) : 615 - 621
  • [9] THE METABOLISM OF PYRAZOLO (3,4-D) PYRIMIDINES BY THE RAT
    FEIGELSON, P
    DAVIDSON, JD
    CANCER RESEARCH, 1958, 18 (02) : 226 - 228
  • [10] A facile synthesis of pyrazolo [3,4-d] pyrimidines
    Trivedi, A. R.
    Dubal, G. G.
    Ravat, N. R.
    Shah, V. H.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 17 (04) : 385 - 386