Preparation of esters and amides from carboxylic acids and N-formylation of amines promoted by 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-hexachloride (TAPC)

被引:27
作者
Bahrami, Kiumars [1 ,2 ]
Khodaei, Mohammad M. [1 ]
Targhan, Homa [1 ]
Arabi, Mehdi Sheikh [1 ]
机构
[1] Razi Univ, Dept Organ Chem, Fac Chem, Kermanshah 6714967346, Iran
[2] Razi Univ, NNRC, Kermanshah 6714967346, Iran
关键词
Organic esters; Carboxamides; N-formylation; Grinding technique; Carboxylic acids; Protection of functional groups; ROOM-TEMPERATURE; EFFICIENT PROCEDURE; SECONDARY-AMINES; USEFUL REAGENT; FACILE METHOD; FORMIC-ACID; CATALYST; MILD; DERIVATIVES; AMIDATION;
D O I
10.1016/j.tetlet.2013.07.033
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method is described for the preparation of esters and amides promoted by TAPC from carboxylic acids using a solvent-free grinding technique. The solvent-free N-formylation of amines is also reported. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5064 / 5068
页数:5
相关论文
共 59 条
  • [1] Silica supported perchloric acid catalyzed rapid N-formylation under solvent-free conditions
    Ansari, Mohd Imran
    Hussain, Mohd Kamil
    Yadav, Nisha
    Gupta, Puneet K.
    Hajela, K.
    [J]. TETRAHEDRON LETTERS, 2012, 53 (16) : 2063 - 2065
  • [2] Supported p-Toluenesulfonic Acid as a Highly Robust and Eco-Friendly Isocyanide Scavenger
    Azuaje, Jhonny
    Coelho, Alberto
    El Maatougui, Abdelaziz
    Manuel Blanco, Jose
    Sotelo, Eddy
    [J]. ACS COMBINATORIAL SCIENCE, 2011, 13 (01) : 89 - 95
  • [3] Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles
    Bahrami, Kiumars
    Khodaei, M. Mehdi
    Naali, Fardin
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) : 6835 - 6837
  • [4] TAPC-Promoted Synthesis of Sulfonyl Chlorides from Sulfonic Acids
    Bahrami, Kiumars
    [J]. SYNLETT, 2011, (18) : 2671 - 2674
  • [5] TAPC-Catalyzed Synthesis of Thioethers from Thiols and Alcohols
    Bahrami, Kiumars
    Khodaei, Mohammad Mehdi
    Khodadoustan, Nayere
    [J]. SYNLETT, 2011, (15) : 2206 - 2210
  • [6] TAPC-Promoted Oxidation of Sulfides and Deoxygenation of Sulfoxides
    Bahrami, Kiumars
    Khodaei, Mohammad M.
    Arabi, Mehdi Sheikh
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (18) : 6208 - 6213
  • [7] H2O2/SOCl2: a useful reagent system for the conversion of thiocarbonyls to carbonyl compounds
    Bahrami, Kiumars
    Khodaei, Mohammad M.
    Farrokhi, Azita
    [J]. TETRAHEDRON, 2009, 65 (36) : 7658 - 7661
  • [8] H2O2/Fe(NO3)3-Promoted Synthesis of 2-Arylbenzimidazoles and 2-Arylbenzothiazoles
    Bahrami, Kiumars
    Khodaei, Mohammad Mehdi
    Naali, Fardin
    [J]. SYNLETT, 2009, (04) : 569 - 572
  • [9] REACTION OF 1,1-DINITROETHANE WITH ITS SALTS
    BELEW, JS
    GRABIEL, CE
    CLAPP, LB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (05) : 1110 - 1114
  • [10] Amberlite IR-120: A Reusable Catalyst for N-Formylation of Amines with Formic Acid Using Microwaves
    Bhojegowd, Madhusudana Reddy Mvthukur
    Nizam, Aatika
    Pasha, Mohamed Afzal
    [J]. CHINESE JOURNAL OF CATALYSIS, 2010, 31 (05) : 518 - 520