Abstract
We present a general efficient green method for the preparation of nitro N,N′-diaryl thioureas via a one-pot method using cyrene as a solvent with almost quantitative yields. This confirmed the viability of cyrene as a green alternative to THF in the synthesis of thiourea derivatives. After screening different reducing conditions, the nitro N,N′-diaryl thioureas were selectively reduced using Zn dust in the presence of water and acid to the corresponding amino N,N′-diaryl thioureas. These were then used to test the installation of the Boc-protected guanidine group with N,N′-bis-Boc protected pyrazole-1-carboxamidine as a guanidylating reagent not requiring mercury(II) activation. Finally, the TFA salts obtained after Boc-deprotection of two sample compounds were tested for their affinity towards DNA showing no binding.
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