Beilstein J. Org. Chem.2012,8, 2100–2105, doi:10.3762/bjoc.8.236
similar MCRs of numerous other aminoazoles, a change of direction of the heterocyclizations in the case of 4-amino-5-carboxamido-1,2,3-triazole was not observed when microwave or thermal heating was substituted by ultrasonication at ambient temperature.
Keywords: 4-amino-5-carboxamido-1,2,3-triazole
] and derivatives of carboxylic acids [25][26]. The only MCR involving this type of aminoazole was described in our previous publication [27].
In the case of 4-amino-5-carboxamido-1,2,3-triazole, heterocyclizations can proceed in two main ways: “classical” for α-aminoazole direction with participation
of the NH2-group and endocyclic NH (Figure 2, compound VII or its position isomer VIII), or an alternative pathway involving the NH2-group and carboxamide fragment [25][26] (compound IX).
Thus, there are several alternative directions for reactions between 4-amino-5-carboxamido-1,2,3-triazole
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Graphical Abstract
Figure 1:
Some MCRs of aminoazoles with controlled switching of the direction.