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EnglishThe reaction of 1,2-diaza-1,3-butadienes with dialkyl phenylphosphonites under solvent-free conditions proceeds via zwitterionic intermediate and gives, by precipitation, the stable ylidic a-phosphanylidenehydrazones that, in turn, can be transformed into the corresponding 3-phenyl-2H-1,2,3lambda5-diazaphospholes. The latter compounds are converted by hydrolytic cleavage in methanol–water (95:5) into E-hydrazonophosphonates that are useful for the preparation of the corresponding b-ketophosphonates and 4-[alkoxy(phenyl)phosphoryl]-1,2-diaza-1,3-butadienes. These peculiar 1,2-diaza-1,3-butadienes, bearing an alkoxy(phenyl)phosphoryl group on the carbon atom in position 4 are also able to add different nucleophiles, such as methanol or thiourea, giving 2-[alkoxy(phenyl)phosphoryl]-2-methoxyhydrazones and 5-phosphinate-substituted thiazol-4-ones, respectively.
| Titolo: | Carbon–phosphorus bond formation and transformation in the reaction of 1,2-diaza-1,3-butadienes with alkyl phenylphosphonites | |
| Autore/i: | O. A. Attanasi; BACCOLINI, GRAZIANO; BOGA, CARLA; L. De Crescentini; P. Filippone; F. Mantellini | |
| Autore/i Unibo: | ||
| Anno: | 2008 | |
| Rivista: | ||
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/j.tet.2008.05.007 | |
| Abstract: | The reaction of 1,2-diaza-1,3-butadienes with dialkyl phenylphosphonites under solvent-free conditions proceeds via zwitterionic intermediate and gives, by precipitation, the stable ylidic a-phosphanylidenehydrazones that, in turn, can be transformed into the corresponding 3-phenyl-2H-1,2,3lambda5-diazaphospholes. The latter compounds are converted by hydrolytic cleavage in methanol–water (95:5) into E-hydrazonophosphonates that are useful for the preparation of the corresponding b-ketophosphonates and 4-[alkoxy(phenyl)phosphoryl]-1,2-diaza-1,3-butadienes. These peculiar 1,2-diaza-1,3-butadienes, bearing an alkoxy(phenyl)phosphoryl group on the carbon atom in position 4 are also able to add different nucleophiles, such as methanol or thiourea, giving 2-[alkoxy(phenyl)phosphoryl]-2-methoxyhydrazones and 5-phosphinate-substituted thiazol-4-ones, respectively. | |
| Data prodotto definitivo in UGOV: | 2008-06-26 13:57:42 | |
| Appare nelle tipologie: | 1.01 Articolo in rivista |
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http://hdl.handle.net/11585/61191
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