Research Article

Nanorod-Shaped Basic Catalyzed N,N-Diformylation of Bisuracil Derivatives: A Greener “NOSE” Approach

Table 1

Optimization of the reaction conditions for the N,N-diformylation of 1a (Scheme 1).

EntryCatalystSolventTemp. (°C)Time (h)Yield (%)b

1NoneSolvent-free409NRc
2NoneSolvent-free809NRc
3NoneH2O4012NRc
4NoneCH3CN4012NRc
5NoneMeOH4012NRc
6NoneEtOH4012NRc
7NoneTHF4012NRc
8NoneToluene4012NRc
9NoneDMSO4012NRc
10NoneXylene4012NRc
11NoneDMF4012NRc
12dK2CO3Solvent-free4012NRc
13dPPh3Solvent-free4012NRc
14dImidazoleSolvent-free4010Trace
15dNano-Al2 Solvent-free4045 min70
16dNano-MgOjSolvent-free40334
17dNano-Fe2 Solvent-free40512
18dNano-Ti Solvent-free 4048
19dNano-Al2 Solvent-free 80243
20eNano-Al2 Solvent-free 40325
21fNano-Al2 Solvent-free 40417
22gNano-Al2 Solvent-free4068

aReaction conditions: bisuracil 1a (1 mmol, 0.454 g), formic acid (6 mmol, 0.66 mL), and solvent (5 mL). bIsolated yields. cNo reaction was observed. d7 mol% catalyst was used. e5 mol% catalyst was used. f3 mol% catalyst was used. g10 mol% catalyst was used. h1 mol% catalyst was used. iParticles size (17.4–16.4 nm). jParticles size (<50 nm). kParticles size (12 nm). lParticles size (<80 nm).