Since its discovery in 1968, the ring opening of 3,4-dinitrothiophene (1) with amines has represented the first step in a number of valuable synthetic pathways. As a matter of fact, the dinitrobutadienediamines (7 or 8) which smoothly form in ethanol at room temperature as a result of a clear example of the non-benzenoid behaviour of 1, are highly-functionalized unsaturated systems whose versatility as building-blocks has so far been exploited for the preparation of linear as well as of homo- and hetero-cyclic molecules. In particular, target heterocycles encompass pyrroles, pyrrolidines, isoxazolines, isoxazoles, oxadiazoles, triazoles: i.e. systems endowed with high potentialities both in synthesis and in pharmacology.
2,3-Dinitro-1,3-butadienes as versatile building-blocks from the ring-opening of 3,4-dinitrothiophene
BIANCHI, LARA;MACCAGNO, MASSIMO;PETRILLO, GIOVANNI;SANCASSAN, FERNANDO;TAVANI, CINZIA
2006-01-01
Abstract
Since its discovery in 1968, the ring opening of 3,4-dinitrothiophene (1) with amines has represented the first step in a number of valuable synthetic pathways. As a matter of fact, the dinitrobutadienediamines (7 or 8) which smoothly form in ethanol at room temperature as a result of a clear example of the non-benzenoid behaviour of 1, are highly-functionalized unsaturated systems whose versatility as building-blocks has so far been exploited for the preparation of linear as well as of homo- and hetero-cyclic molecules. In particular, target heterocycles encompass pyrroles, pyrrolidines, isoxazolines, isoxazoles, oxadiazoles, triazoles: i.e. systems endowed with high potentialities both in synthesis and in pharmacology.
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