Synthesis of new tetracyclic benzo[4,5]furo[3,2-d]-1,2,4-triazolo [1,5-a]pyrimidin-5(1H)-ones via a tandem aza-Wittig/Heterocumulene-mediated annulation

被引:3
|
作者
Hu, Yang-Gen [1 ,2 ]
Yang, Sheng-Jun [1 ]
Ding, Ming-Wu [1 ]
机构
[1] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China
[2] Yunyang Med Coll, Dept Med Chem, Shiyan 442000, Peoples R China
基金
中国国家自然科学基金;
关键词
Benzo[4,5]furo[3,2-d]-1,2,4-triazolo[1,5-a]pyrimidin-5(1H)-one; iminophosphorane; aza-Wittig reaction; isocyanate;
D O I
10.3998/ark.5550190.0009.f26
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The carbodiimides 3, obtained from aza-Wittig reactions of iminophosphorane 2 with aromatic isocyanates, reacted with hydrazine to give selectively 3-amino-2-arylaminobenzofuro[3,2-d]pyrimidin-4(3H)-ones 5. Reactions of 5 with triphenylphosphine, hexachloroethane and triethylamine produced iminophosphoranes 6. A tandem aza-Wittig reaction of iminophosphorane 6 with isocyanate or acyl chloride generated previously unreported tetracyclic benzo[4,5]furo[3,2-d]-1,2,4-triazolo[1,5-a]pyrimidin-5(1H)-ones 8 or 10 in high yields.
引用
收藏
页码:297 / 306
页数:10
相关论文
共 50 条
  • [21] Synthesis of ethyl 4,5-disubstituted 2-azido-3-thiophenecarboxylates and use in the synthesis of thieno[3,2-e][1,2,3]triazolo[1,5-a]pyrimidin-5(4H)-ones
    Pokhodylo, Nazady T.
    Matiychuk, Vasyl S.
    Obushak, Mykola D.
    TETRAHEDRON, 2009, 65 (13) : 2678 - 2683
  • [22] Synthesis and anticonvulsant activity of 7-phenyl-6,7-dihydro-[1,2,4] triazolo[1,5-a]pyrimidin-5(4H)-ones and their derivatives
    Deng, Xian-Qing
    Quan, Li-Na
    Song, Ming-Xia
    Wei, Cheng-Xi
    Quan, Zhe-Shan
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (07) : 2955 - 2963
  • [23] Iminophosphorane-mediated efficient synthesis of new tricyclic 3,5-dihydro-1,2,3-triazolo[4,5-d]-1,2,4-triazolo[1,5-a]pyrimidin-9-ones
    Zhao, JF
    Xie, C
    Xu, SZ
    Ding, MW
    Xiao, WJ
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (01) : 130 - 134
  • [24] A facile approach to 4,5-dihydro[1,2,4]triazolo[3,2-d][1,5]benzoxazepines
    Meng, Qingqing
    Bai, Hexiang
    Li, Zhiming
    Wang, Quanrui
    Tao, Fenggang
    SYNTHESIS-STUTTGART, 2007, (11): : 1629 - 1634
  • [25] Reactions of tetrahydropyrido[4,5-d][1,2,4]triazolo[1,5-a]-pyrimidin-4-ones with activated alkynes. Synthesis of [1,2,4]triazolo[1',5':1,2]pyrimido[4,5-d]azocines
    Voskressensky, L. G.
    Borisova, T. N.
    Ovcharov, M. V.
    Sorokina, E. A.
    Khrustalev, V. N.
    Varlamov, A. V.
    RUSSIAN CHEMICAL BULLETIN, 2012, 61 (08) : 1603 - 1608
  • [26] Reactions of tetrahydropyrido[4,5-d][1,2,4]triazolo[1,5-a]-pyrimidin-4-ones with activated alkynes. Synthesis of [1,2,4]triazolo[1′,5′:1,2]pyrimido[4,5-d]azocines
    L. G. Voskressensky
    T. N. Borisova
    M. V. Ovcharov
    E. A. Sorokina
    V. N. Khrustalev
    A. V. Varlamov
    Russian Chemical Bulletin, 2012, 61 : 1603 - 1608
  • [27] SYNTHESIS OF SOME [1,2,4]TRIAZOLO[4,3-A]THIENO[3,2-E]PYRIMIDIN-5(4H)-ONES
    PATHAK, US
    GANDHI, NV
    SINGH, S
    WARDE, RP
    JAIN, KS
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1992, 31 (04): : 223 - 229
  • [28] An expedient synthesis of novel [1,2,4]triazolo[3,2-d] [1,5]benzothiazepine] derivatives
    Liu, XJ
    Wang, QR
    Liu, Y
    Fan, YB
    Ding, ZB
    SYNTHESIS-STUTTGART, 2000, (03): : 435 - 441
  • [29] Synthesis of substituted benzo[4′,5′]furo[2′,3′:4,5]pyrrolo[1,2-d][1,2,4]triazolo[3,4-f][1,2,4]triazines
    Sleziak, R
    Krutosikova, A
    CHEMICAL PAPERS, 1997, 51 (6B) : 412 - 415
  • [30] SYNTHESIS OF SUBSTITUTED 3H,5H-1,2,4-TRIAZOLO[1,5-A]-PYIMIDINES
    JAENECKE, G
    MEISTER, L
    DRESSEL, L
    RICHTER, R
    VOIGT, H
    ZEITSCHRIFT FUR CHEMIE, 1989, 29 (10): : 378 - 379