Ambident reactivity of enolizable 5-mercapto-1H-tetrazoles in trapping reactions with in situ-generated thiocarbonyl S-methanides derived from sterically crowded cycloaliphatic thioketones

• Grzegorz Mlostoń,
• Małgorzata Celeda,
• Marcin Palusiak,
• Heinz Heimgartner,
• Marta Denel-Bobrowska and
• Agnieszka B. Olejniczak

Beilstein J. Org. Chem. 2025, 21, 1508–1519, doi:10.3762/bjoc.21.113

• derived from 5-mercapto-1H-tetrazoles was also examined. Keywords: 2,5-dihydro-1,3,4-thiadiazoles; enolizable 5-mercapto-1H-tetrazoles; insertion reactions; thiiranes; thiocarbonyl ylides; X-ray analysis; Introduction Cycloaddition reactions, including 1,3-dipolar cycloadditions, are considered as one

• the substitution pattern of both substrates, i.e., substituent Ar in the starting cyclopropane 3 and the R–N(1) moiety in the tetrazole derivative 4 [15]. Taking into account the known and widely documented importance of enolizable 5-mercapto-1H-tetrazoles as important bioisosters [17][18][19][20][21

• situ-generated 1 towards enolizable 5-mercapto-1H-tetrazoles 4 bearing various aliphatic and aromatic substituents at the N(1) atom. Competition between the expected S–H and N–H insertion processes was of primary interest. In extension of the synthetically oriented study, bioactivity of selected