Categories: Synthesis of N-Heterocycles, Synthesis of S-Heterocycles >
Synthesis of 1,2,4-thiadiazoles
An electro-oxidative intramolecular dehydrogenative N-S bond formation of
imidoyl thioureas provides a broad range of 3-substituted
5-amino-1,2,4-thiadiazoles derivatives in good to excellent yields with
excellent functional group tolerance under catalyst- and oxidant-free conditions
at room temperature.
Z. Yang, J. Zhang, L. Hu, L. Li, K. Liu, T. Yang, C. Zhou, J. Org. Chem., 2020, 85,
3358-3363.
I2-mediated oxidative C-N and N-S bond formations in water enable a
metal-free, environmentally benign and convenient strategy for the synthesis of
4,5-disubstituted/N-fused 3-amino-1,2,4-triazoles and 3-substituted
5-amino-1,2,4-thiadiazoles from isothiocyanates. The scalable protocols
exhibited excellent substrate tolerance.
N. Jatangi, N. Tumula, R. K. Palakodety, M. Nakka, J. Org. Chem., 2018, 83,
5715-5723.
An intramolecular oxidative S-N bond formation of imidoyl thioureas mediated by
phenyliodine(III) bis(trifluoroacetate) enables an efficient, metal-free
synthesis of 3-substituted-5-arylamino-1,2,4-thiadiazoles. The protocol offers
broad substrate scope, very short reaction times and very good yields.
A. Mariappan, K. Rajaguru, N. M. Chola, S. Muthusubramanian, N. Bhuvanesh, J. Org. Chem.,
2016, 81, 6573-6579.
