Regioselective Access to 1, 2‐Diarylhistidines through the Copper‐Catalyzed N1‐Arylation of 2‐Arylhistidines. Issue 5 (6th February 2017)

• Record Type: Journal Article
• Authors: Sharma, Krishna K.; Mandloi, Meenakshi; Jain, Rahul
• Is Part Of: European journal of organic chemistry. Issue 5(2017)
• Page Start: 984
• Page End: 988
• Publication Date: 2017-02-06
• Subjects: Amino acids -- Arylation -- Copper -- Cross‐coupling -- Microwave chemistry; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601566
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : We report the copper(I)‐catalyzed synthesis of 1, 2‐diarylhistidines through the N1‐arylation of protected 2‐arylhistidines in the presence of 8‐hydroxyquinoline as a ligand and aryl iodides as electrophilic coupling partners under microwave irradiation at 140 °C. This method provides regioselective access to previously inaccessible multisubstituted histidines with intact chirality in high yields. The synthesized 1, 2‐diarylated histidines are a hitherto unknown class of derivatives with untapped potential in modified amino acid based peptide and peptidomimetic drug discovery. Abstract : The Cu I ‐catalyzed synthesis of 1, 2‐diarylhistidines through the N1‐arylation of protected 2‐arylhistidines in the presence of 8‐hydroxyquinoline as a ligand and aryl iodides as electrophilic coupling partners under microwave irradiation at 140 °C is presented. This method provides regioselective access to previously inaccessible multisubstituted histidines with intact chirality in high yields.