Three component condensation of N,N-dimethylurea, paraformaldehyde and primary amines using montmorillonite K-10 in dry media under microwave irradiation leads to triazones 5a-f in high yields.
References
1.
AbramovitchR. A., Org. Prep. Proc. Int., 1991, 23, 683; MingosD. M. P. and BaghurstD. R., Chem. Soc. Rev., 1991, 20, 1; S. Caddick, Tetrahedron, 1995, 51, 10403; C. R. Strauss and R. W. Trainer, Aust. J. Chem., 1995, 48, 1665.
2.
DeloudeL. and LaszloP., J. org. Chem., 1996, 61, 6360; VarmaR. S. and DahiyaR., SynLett, 1997, 857; VarmaR. S. and MeshramH. M., Tetrahedron Lett., 1997, 38, 7973.
3.
AugustineR. L., Heterogenous Catalysis for the Synthetic Chemist, Marcell Decker Inc., New York, 1996, pp. 579-584; SmithK., Solid Supports and Catalysts in Organic Synthesis, Ellis Harwood, Chichester, 1992; PerioB., DoziasM. J., JacquaultP. and HamelinJ., Tetrahedron Lett., 1997, 38, 7867; Jolivet-FauchetS., HamelinJ., Texier-BoulletF., ToupetL. and JacquaultP., Tetrahedron, 1998, 54, 4561; ToshimaK., UshilciY., MatsuoG. and MatsumuraS., Tetrahedron Lett., 1997, 38, 7375.
4.
PetersonH., Synthesis, 1973, 243.
5.
HardiesD. E. and KrassD. K., US Pat., 4150220, 1979 (Chem. Abstr., 1979, 91, P57062e).
6.
HardiesD. E., US Pat., 4152516, 1979 (Chem. Abstr., 1979, 91, P57063f).
7.
KnappS., HaleJ. J., BastosM., MolinaA. and YuK., J. Org. Chem., 1992, 57, 6239.