‘Green’ methodology for efficient and selective benzoylation of nucleosides using benzoyl cyanide in an ionic liquid

• Published in: Bioorganic & medicinal chemistry 2005-07, Vol.13 (14), p.4467-4472
• Main Authors: Prasad, Ashok K., Kumar, Vineet, Malhotra, Shashwat, Ravikumar, Vasulinga T., Sanghvi, Yogesh S., Parmar, Virinder S.
• Format: Article
• Language: English
• Subjects: Antigene; Antisense; Benzoates - chemistry; Benzoylation; Carbohydrates. Nucleosides and nucleotides; Chemistry; Cyanides - chemistry; Exact sciences and technology; Ionic liquids; Ions; Magnetic Resonance Spectroscopy; Nucleosides; Nucleosides - chemistry; Nucleosides, nucleotides and oligonucleotides; Organic chemistry; Preparations and properties
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2005.04.038

Efficient benzoylation of various nucleosides (both ribo- and 2′-deoxyribo), phenols, aromatic amines, benzyl alcohol, aliphatic diols, 3-aminophenol and 2-aminobenzylalcohol has been accomplished using benzoyl cyanide in ionic liquid 1-methoxyethyl-3-methylimidazolium methanesulfonate with catalytic amount of DMAP under ambient conditions. Benzoyl cyanide in the ionic liquid 1-methoxyethyl-3-methylimidazolium methanesulfonate has been employed as a ‘green’ alternative and mild reaction condition protocol to conventional pyridine–benzoyl chloride system for efficient and selective benzoylation of nucleosides (of both the ribo- and deoxyribo-series) at ambient temperatures. The use of benzoyl cyanide–ionic liquid combination has been successfully extended for highly efficient benzoylation of phenols, aromatic amines, benzyl alcohol, aliphatic diols, 3-aminophenol and 2-aminobenzylalcohol, which indicates the versatility of this benzoylating system.