A new flexible strategy for the synthesis of diversely functionalized pyridazines from 4-chloro-1,2-diaza-1,3-butadienes and active methylene compounds is reported. The high chemoselectivity of this approach offers access to structural precursors of GABA-A antagonist analogues.
This paper reviews our nearly twenty-five years' activity on 1,2-diaza-1,3-butadienes and shows that these compounds are powerful tools in organic chemistry. In fact, α-substituted-, α-oxo-, and α,β-unsaturated-hydrazones, have been obtained from 1,2-diaza-1,3-butadienes, as have pyrroles,
A new and efficient synthesis of polysubstituted pyrroles by a sequential one-pot three-component reaction between primary aliphatic amines, active methylene compounds, and 1,2-diaza-1,3-dienes (DDs) is reported. The reactions were performed without catalyst and under solvent-free conditions with complete control of pathway selectivity. Notably, the ready availability of the starting materials and the high level of practicability of the reaction and work up make this approach an attractive complementary method for access to unknown polysubstituted pyrroles.
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