Divergent and Chemoselective Transformations of Thioamides with Designed Carbene Equivalents

• 小林, 祐輔

  Graduate School of Pharmaceutical Sciences, Kyoto University

• 竹本, 佳司

  Graduate School of Pharmaceutical Sciences, Kyoto University

• Takemoto, Yoshiji

  Graduate School of Pharmaceutical Sciences, Kyoto University

抄録

The reactions of thioamides with ortho‐nitro‐substituted iodonium ylides proceeded under mild conditions to give enaminones or thiazoles, depending on the iodonium ylide used. This protocol allowed the use of protic solvents, including aqueous solutions, and therefore coupling reactions with complex molecules such as peptides or steroids were possible. A mild and efficient method for the synthesis of various iodonium ylides was established. DFT calculations suggested that the halogen bonding between a thioamide and iodonium ylide was important in this chemoselective coupling reaction. The potential use of enaminones conjugated with pharmaceuticals as prodrugs was also demonstrated.

収録刊行物

• Chemistry - A European Journal

  Chemistry - A European Journal 25 (44), 10314-10318, 2019-08-06

  Wiley

キーワード

• chemoselectivity
• enaminones
• halogen bonding
• hypervalent compounds
• thiazoles

詳細情報

• CRID: 1050845763351185152
• NII論文ID: 120006712297
• NII書誌ID: AA11076269
• ISSN: 09476539
• ISSN: 15213765
• DOI: 10.1002/chem.201902699
• HANDLE: 2433/243264
• Web Site: https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.201902699
• Web Site: https://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.201902699
• Web Site: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chem.201902699
• 本文言語コード: en
• 資料種別: journal article
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