An efficient synthesis of cyanamide from amine promoted by a hypervalent iodine(III) reagent

被引:48
|
作者
Ghosh, Harisadhan [1 ]
Yella, Ramesh [1 ]
Ali, Abdur Rezzak [1 ]
Sahoo, Santosh K. [1 ]
Patel, Bhisma K. [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Gauhati 781039, Assam, India
关键词
TRANSFORMATION; DERIVATIVES; CHEMISTRY; MILD;
D O I
10.1016/j.tetlet.2009.03.017
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In a one-pot strategy we have achieved an efficient method for the synthesis of organic cyanamides starting from dithiocarbamic acid salts/amines. In this strategy the in situ generated alkyl or aryl isothiocyanates, obtained by the desulfurization of dithiocarbamic acid salts with diacetoxyiodobenzene (DIB) react with aqueous ammonia forming alkyl OF aryl thiourea which on subsequent oxidative desulfurization with DIB led to the formation of corresponding cyanamide in good yields. Mild reaction conditions, shorter reaction time, an environmentally benign protocol, and easy isolation of the desired product make the present methodology a Suitable alternative for the preparation of various organic cyanamides. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2407 / 2410
页数:4
相关论文
共 50 条
  • [1] Novel and efficient synthesis of pyrroloiminoquinones using a hypervalent iodine(III) reagent
    [J]. Jornal of the Chemical Society. Perkin Transactions 1, (04):
  • [2] Novel and efficient synthesis of pyrroloiminoquinones using a hypervalent iodine(III) reagent
    Kita, Y
    Watanabe, H
    Egi, M
    Saiki, T
    Fukuoka, Y
    Tohma, H
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (04): : 635 - 636
  • [3] Hypervalent iodine(III) promoted synthesis of isothiocyanates in water
    Racheeti, Prasanna Babu
    Gunturu, Ratna Babu
    Pinapati, Srinivasa Rao
    Kowthalam, Anitha
    Tamminana, Ramana
    Rudraraju, Rameshraju
    [J]. SYNTHETIC COMMUNICATIONS, 2023, 53 (01) : 23 - 31
  • [4] Rapid transformation of sulfinate salts into sulfonates promoted by a hypervalent iodine(III) reagent
    Deruer, Elsa
    Hamel, Vincent
    Blais, Samuel
    Canesi, Sylvain
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 : 1203 - 1207
  • [5] HIGHLY EFFICIENT METHOD FOR SYNTHESIS OF BENZOQUINONES USING HYPERVALENT IODINE(III) REAGENT AND SODIUM BISULFATE
    Sasane, Kulbhushan A.
    Telvekar, Vikas N.
    [J]. SYNTHETIC COMMUNICATIONS, 2014, 44 (04) : 468 - 473
  • [6] The efficient synthesis of morphinandienone alkaloids by using a combination of hypervalent iodine(III) reagent and heteropoly acid
    Hamamoto, H
    Shiozaki, Y
    Nambu, H
    Hata, K
    Tohma, H
    Kita, Y
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (20) : 4977 - 4982
  • [7] Novel and efficient synthesis of sulfur-containing heterocycles using a hypervalent iodine(III) reagent
    Kita, Y
    Egi, M
    Ohtsubo, M
    Saiki, T
    Takada, T
    Tohma, H
    [J]. CHEMICAL COMMUNICATIONS, 1996, (19) : 2225 - 2226
  • [8] A Simple and Efficient Method for the Synthesis of Novel Pyrazolyl Isoxazoline Derivatives Using Hypervalent Iodine (III) Reagent
    Kumar, Rajesh
    Kumar, Manoj
    Prakash, Om
    [J]. HETEROATOM CHEMISTRY, 2016, 27 (04) : 228 - 234
  • [9] An Efficient Catalytic Sulfonyloxylactonization of Alkenoic Acids Using Hypervalent Iodine(III) Reagent
    Yan, Jie
    Wang, Hong
    Yang, Zhenping
    He, Yan
    [J]. SYNLETT, 2009, (16) : 2669 - 2672
  • [10] Synthesis of diols using the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate)
    Celik, Murat
    Alp, Cemalettin
    Coskun, Betul
    Gultekin, M. Serdar
    Balci, Metin
    [J]. TETRAHEDRON LETTERS, 2006, 47 (22) : 3659 - 3663