Thiadiazoles, phosphorylated

Condensation of 3-amino-5-(l,2,3,4-tetrahydrocarbazol-9-ylmethyl)-l,3,4-thiadizole with chloroacetic acid affords compound 339 that on treatment with phosphoryl chloride cyclizes to 2-( 1,2,3,4-tetrahy drocarbazol-9-ylmethyl)-imidazo[2,l- ][l,3,4]thiadiazole-5-(67/)-one 340 (Equation 62) < 1998IJH231 >. 

Substituted 2-aniIino-l,3,4-thiadiazoles uncouple oxidative phosphorylation in rat liver mitochondria and photosynthetic phosphorylation in spinach chloroplasts (75ZN(C)183). 

Several important reactions of (diazoalkyl)phosphonic esters and related compounds are essentially 1,3-dipolar additions, either inter- or intra-molecular in nature, and as such are considered in Section V.D. The compound 187 (R = H) is unstable and, when prepared, cyclizes spontaneously to the phosphorylated triazole 188 but the same conversion with R = Me or Et is achieved by the action of KOBu The nitrosation of the aminoacetonitriles 189 with propyl nitrite does not have the disadvantages that other synthetic routes to the diazoacetonitriles 190 possess further reaction between 190 and H2S yields the phosphorylated thiadiazoles 191. ... 

Substituted 2-anilino-l,3,4-thiadiazoles inhibit oxidative phosphorylation (in rat liver mitochondria) and photosynthetic phosphorylation (in spinach chloroplasts). ... 

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