An efficient copper-catalyzed synthesis of substituted 2,4-diamino-1,3,5-triazines from 1,1-dibromoalkenes and biguanides under mild conditions has been developed. The reaction occurred in moderate to good yields and tolerated alkyl-, heterocyclic-, or aryl-substituted 1,1-dibromoalkenes containing functionalities such as nitriles, ethers, and halogens. Monosubstituted to tetrasubstituted biguanidines also afforded the desired products.

We have developed a useful and simple process for the NaOH-promoted reaction of 1,1-dihaloalkenes and 1H-azoles to afford dipyrazolyl alkenes under mild and transition-metal-free conditions.

The timing of operation for acquired rectourethral or urethrovaginal fistula is appropriate at least 6 months after the last procedure. The 1-stage York-Mason procedure for the repair of the fistula is feasible and effective.

Copper-catalyzed intermolecular annulation of 2-amine-[1,3,5]­triazines and aryl nitriles for the synthesis of [1,2,4]­triazolo­[1,5-a]­[1,3,5]­triazines via N–C bond formation and oxidative N–N coupling [oxidative 3 + 2 cyclization] is presented. A wide range of aryl nitriles, including electron-rich benzonitriles, electron-poor benzonitriles, 2-cyanothiophene, and 4-cyanopyridine, were all functionalized with 2-amine-[1,3,5]­triazines. Furthermore, amidation of 2-amine-[1,3,5]­triazines via Cu-catalyzed C–CN bond cleavage of phenylacetonitriles is also demonstrated. The reaction occurred in moderate to satisfactory yields and tolerated alkyl- or aryl-substituted 2-amine-[1,3,5]­triazines. Aniline, aminopyridine, and aminopyrimidine also afforded the desired products.