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Collect. Czech. Chem. Commun. 2000, 65, 621-630
https://doi.org/10.1135/cccc20000621

A Facile Synthesis of Carboxamides by Dehydration Condensation Between Free Carboxylic Acids and Amines Using O,O'-Di(2-pyridyl) Thiocarbonate as a Coupling Reagent

Isamu Shiina, Katsuyuki Saitoh, Masakazu Nakano, Yoshihito Suenaga and Teruaki Mukaiyama*

Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan

Crossref Cited-by Linking

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  • Rouhi-Saadabad Hamed, Akhlaghinia Batool: A One-Pot, fast, and efficient amidation of carboxylic acids, α-amino acids and sulfonic acids using pph3/n-chlorobenzotriazole system. Phosphorus, Sulfur, and Silicon and the Related Elements 2015, 190, 1703. <https://doi.org/10.1080/10426507.2015.1024313>
  • Valeur Eric, Bradley Mark: Amide bond formation: beyond the myth of coupling reagents. Chem. Soc. Rev. 2009, 38, 606. <https://doi.org/10.1039/B701677H>
  • Shiina Isamu, Ushiyama Hisaya, Yamada Yo-ko, Kawakita Yo-ichi, Nakata Kenya: 4-(Dimethylamino)pyridineN-oxide (DMAPO): An Effective Nucleophilic Catalyst in the Peptide Coupling Reaction with 2-Methyl-6-nitrobenzoic Anhydride. Chem. Asian J. 2008, 3, 454. <https://doi.org/10.1002/asia.200700305>
  • Tozawa Takashi, Yamane Yoshinobu, Mukaiyama Teruaki: An Effective Method for the Synthesis of Carboxamides by Using Tetrakis(pyridine-2-yloxy)silane as a Mild Coupling Reagent. Chem. Lett. 2005, 34, 1334. <https://doi.org/10.1246/cl.2005.1334>
  • Shiina Isamu, Kawakita Yo-ichi: The effective use of substituted benzoic anhydrides for the synthesis of carboxamides. Tetrahedron 2004, 60, 4729. <https://doi.org/10.1016/j.tet.2004.03.066>
  • Wakasugi Kazunori, Nakamura Atsushi, Iida Akira, Nishii Yoshinori, Nakatani Nobuji, Fukushima Shoji, Tanabe Yoo: Novel and efficient method for esterification, amidation between carboxylic acids and equimolar amounts of alcohols, and amines utilizing Me2NSO2Cl and N,N-dimethylamines; its application to the synthesis of coumaperine, a natural chemopreventive dieneamide. Tetrahedron 2003, 59, 5337. <https://doi.org/10.1016/S0040-4020(03)00734-8>
  • Shiina Isamu, Saitoh Katsuyuki, Nakano Masakazu, Suenaga Yoshihito, Mukaiyama Teruaki: ChemInform Abstract: A Facile Synthesis of Carboxamides by Dehydration Condensation Between Free Carboxylic Acids and Amines Using O,O′-Di(2-pyridyl) Thiocarbonate as a Coupling Reagent. ChemInform 2000, 31, no. <https://doi.org/10.1002/chin.200038073>
  • Shiina Isamu, Suenaga Yoshihito, Nakano Masakazu, Mukaiyama Teruaki: A Convenient Method for the Preparations of Carboxamides and Peptides by Using Di(2-pyridyl) Carbonate and O,O′-Di(2-pyridyl) Thiocarbonate as Dehydrating Reagents. BCSJ 2000, 73, 2811. <https://doi.org/10.1246/bcsj.73.2811>