Beilstein J. Org. Chem.2024,20, 912–920, doi:10.3762/bjoc.20.81
and Heck cyclization reactions. The integration of the multicomponent and post-condensation reactions in one-pot maximizes the pot-, atom-, and step-economy (PASE).
Keywords: Heck reaction; one-pot; tetrahydroisoquinoline; tetrazolo-pyrazino[2,1-a]isoquinolin-6(5H)-ones; tetrazole; Ugi-azide reaction
and 13C NMR, and HRMS analysis. In addition, single crystals of compound 6d and 8c were obtained for X-ray analysis to confirm the structures (Figure 2).
Conclusion
In conclusion, we have developed a one-pot synthesis with two or three steps for making tetrazolo-pyrazino[2,1-a]isoquinolin-6(5H)-ones
-pyrazino[2,1-a]isoquinolin-6(5H)-ones 6c–k in 73–79% yields. The presence of electron-donating or electron-withdrawing groups on the aromatic ring did not show significant effects on the Heck reaction.
Products 6c–k were obtained in higher yields than products 6a,b. We believe that the secondary amine in
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Graphical Abstract
Figure 1:
Representative bioactive tetrazole- and tetrahydroisoquinoline-containing compounds.