Synthesis and antimicrobial activity of 1H-1,2,3-triazole and carboxylate analogues of metronidazole

• Satya Kumar Avula,
• Syed Raza Shah,
• Khdija Al-Hosni,
• Muhammad U. Anwar,
• Rene Csuk,
• Biswanath Das and
• Ahmed Al-Harrasi

Beilstein J. Org. Chem. 2021, 17, 2377–2384, doi:10.3762/bjoc.17.154

• agents; carboxylate analogues; 1H-1,2,3-triazole analogues; metronidazole; synthesis; Introduction Metronidazole (1) is an important antimicrobial agent which has been clinically used successfully for a long time. It was originally used for the treatment of infections caused by Trichomonas varginalis

• + H)+ supported the structure of 1H-1,2,3-triazole compound 5c. Single crystals of 1H-1,2,3-triazole compound 5c were grown from slow evaporation of MeOH. The structure of 1H-1,2,3-triazole compound 5c was unambiguously confirmed by single crystal X-ray analysis (Figure 4). Synthesis of carboxylate

• analogues of metronidazole Compound 1 reacted with different acid chlorides (6a–e) in the presence of pyridine, a catalytic amount of DMAP and in dry DCM at room temperature. The reaction proceeded smoothly to give the desired metronidazole carboxylate derivatives 7a–e in 86–93% yields [21][22]. The

Recent advances in direct C–H arylation: Methodology, selectivity and mechanism in oxazole series

• Cécile Verrier,
• Pierrik Lassalas,
• Laure Théveau,
• Guy Quéguiner,
• François Trécourt,
• Francis Marsais and
• Christophe Hoarau

Beilstein J. Org. Chem. 2011, 7, 1584–1601, doi:10.3762/bjoc.7.187

• units that occur in natural products (Scheme 10). As an example of application in materials, Hoarau recently reported a novel, sequential, palladium-catalyzed, direct arylation of ethyl oxazole-4-carboxylate, giving a rapid access to DPO and POPOP (di)carboxylate analogues (Scheme 11). Two novel sensors