Microwave-assisted cycloaddition of diisopropyl diazomethylphosphonate to electron-deficient alkenes: synthesis of multifunctionalized phosphonopyrazolynes and phosphonopyrazoles

An efficient method for the synthesis of functionalized phosphonopyrazolines has been developed. The procedure involved the microwave-assisted cycloaddition of diisopropyl diazomethylphosphonate to dipolarophiles, such as α,β-unsaturated-nitriles and -esters, performed in neat conditions. By oxidati...

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Bibliographic Details
Published in:Tetrahedron 2014-12, Vol.70 (50), p.9485-9491
Main Authors: Marinozzi, Maura, Tondi, Silvia, Marcelli, Gloria, Giorgi, Gianluca
Format: Article
Language:English
Subjects:
1,3-Dipolar cycloaddition
Alkenes
Cycloaddition
Phosphonopyrazoles
Phosphonopyrazolines
Phosphorous-containing diazo compounds
Privileged structures
Spectroscopy
Synthesis (chemistry)
Tetrahedrons
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Summary:An efficient method for the synthesis of functionalized phosphonopyrazolines has been developed. The procedure involved the microwave-assisted cycloaddition of diisopropyl diazomethylphosphonate to dipolarophiles, such as α,β-unsaturated-nitriles and -esters, performed in neat conditions. By oxidative aromatization the phosphonopyrazolines, thus obtained, were converted into the corresponding phosphonopyazoles. Alternatively, phosphonopyazoles could be obtained by a one-pot, two step procedure directly from dipolarophiles, thus avoiding the isolation of the intermediate pyrazolines. Full spectroscopic characterization of the compounds has been also reported. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.10.069