title: Direct Substitution of Arylalkynyl Carbinols Provides Access to Diverse Terminal Acetylene Building Blocks.
abstract: To develop next generation antifolates for the treatment of trimethoprim-resistant bacteria, synthetic methods were needed to prepare a diverse array of 3-aryl-propynes with various substitutions at the propargyl position. A direct route was sought whereby nucleophilic addition of acetylene to aryl carboxaldehydes would be followed by reduction or substitution of the resulting propargyl alcohol. The direct reduction, methylation, and dimethylation of these readily available alcohols provide efficient access to this uncommon functional array. In addition, an unusual silane exchange reaction was observed in the reduction of the propargylic alcohols.
authors.affiliation: Department of Pharmaceutical Sciences, University of Connecticut , Storrs, Connecticut 06269, United States.
authors.forename: Narendran
authors.identifier: 0000-0002-8922-4339
authors.initials: N
authors.lastname: G-Dayanandan
authors.affiliation: Department of Pharmaceutical Sciences, University of Connecticut , Storrs, Connecticut 06269, United States.
authors.forename: Eric W
authors.initials: EW
authors.lastname: Scocchera
authors.affiliation: Department of Pharmaceutical Sciences, University of Connecticut , Storrs, Connecticut 06269, United States.
authors.forename: Santosh
authors.initials: S
authors.lastname: Keshipeddy
authors.affiliation: Department of Pharmaceutical Sciences, University of Connecticut , Storrs, Connecticut 06269, United States.
authors.forename: Heather F
authors.initials: HF
authors.lastname: Jones
authors.affiliation: Department of Pharmaceutical Sciences, University of Connecticut , Storrs, Connecticut 06269, United States.
authors.forename: Amy C
authors.initials: AC
authors.lastname: Anderson
authors.affiliation: Department of Pharmaceutical Sciences, University of Connecticut , Storrs, Connecticut 06269, United States.|Department of Chemistry, University of Connecticut , Storrs, Connecticut 06269, United States.
authors.forename: Dennis L
authors.identifier: 0000-0003-4634-3351
authors.initials: DL
authors.lastname: Wright
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis*; D000447:Aldehydes / Q000737:chemistry; D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry*; D015195:Drug Design; D024881:Drug Resistance, Bacterial; D005493:Folic Acid Antagonists / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D008745:Methylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014295:Trimethoprim / Q000494:pharmacology
chemical_list: D000438:Alcohols; D000447:Aldehydes; D000480:Alkynes; D000900:Anti-Bacterial Agents; D005493:Folic Acid Antagonists; D014295:Trimethoprim