'Synthesis of bistiadiazolines from D-glucose derived 3-deoxy-1,2-bis(thiosemicarbazone).

MARTINS ALHO MIRIAM A; D'ACCORSO NORMA B.; VARELA OSCAR

Curitiba - Brasil

Congreso; IX Brazilian Meeting on Organic Synthesis.; 2001

Socidad Brasilera de Química

Thiosemicarbazones are suitable starting materials for the synthesis of such heterocyclic compounds as 1,3,4-thiadiazoles and 1,3,4-thiadiazolines1,2. These heterocycles have displayed antifungical and antiviral activities. Furthermore, metal chelates of a 3-deoxyaldos-2-ulose bis(thiosemicarbazone) have also shown antiviral activity 3. We now report the bis-heterocyclization of the 3-deoxyaldos-2-ulose bis(thiosemicarbazone) derived from D-glucose to the corresponding bisthiadiazoline under acetylating conditions. From the reaction mixture was isolated crystalline the major component (1) in a 62 % yield. Compound (1) was fully charaterized by spectroscopic methods, except of the configuration of the C-1 and C-2 stereocenters. For this reason, the X-ray diffraction of a single crystal of 1 was performed and the configuration established as (1R, 2R).1,2. These heterocycles have displayed antifungical and antiviral activities. Furthermore, metal chelates of a 3-deoxyaldos-2-ulose bis(thiosemicarbazone) have also shown antiviral activity 3. We now report the bis-heterocyclization of the 3-deoxyaldos-2-ulose bis(thiosemicarbazone) derived from D-glucose to the corresponding bisthiadiazoline under acetylating conditions. From the reaction mixture was isolated crystalline the major component (1) in a 62 % yield. Compound (1) was fully charaterized by spectroscopic methods, except of the configuration of the C-1 and C-2 stereocenters. For this reason, the X-ray diffraction of a single crystal of 1 was performed and the configuration established as (1R, 2R).3. We now report the bis-heterocyclization of the 3-deoxyaldos-2-ulose bis(thiosemicarbazone) derived from D-glucose to the corresponding bisthiadiazoline under acetylating conditions. From the reaction mixture was isolated crystalline the major component (1) in a 62 % yield. Compound (1) was fully charaterized by spectroscopic methods, except of the configuration of the C-1 and C-2 stereocenters. For this reason, the X-ray diffraction of a single crystal of 1 was performed and the configuration established as (1R, 2R).1) in a 62 % yield. Compound (1) was fully charaterized by spectroscopic methods, except of the configuration of the C-1 and C-2 stereocenters. For this reason, the X-ray diffraction of a single crystal of 1 was performed and the configuration established as (1R, 2R).1 was performed and the configuration established as (1R, 2R).