Déplacements homolytiques intramoléculaires 28. Décompositions induites de derivés peroxydiques 4,5- et 5,6-insaturés à double liaison activée

Ramon, Fabienne; Degueil-Castaing, Marie; Maillard, B.

doi:10.1016/s0014-3057(99)00076-2

Cited by 2 publications

(1 citation statement)

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“…14 The reaction of α-chlorohydrazone 2 with triethylamine results in the in situ generation of the corresponding nitrile imine 6h,i,8a which combines with 1 in a 1,3-dipolar fashion to afford the highly functionalized 5,5-disubstituted pyrazoline in moderate to good yields as a single regioisomer. 15 (Scheme 1) The 1,3-dipolar cycloaddition of 1 with a variety of substituted aromatic nitrile imines was then pursued in order to investigate the scope and limitations of 5,5-disubstituted pyrazolines as precursors to spiropyazolines via the intramolecular cyclization/methylation synthetic methodology.…”

Section: Resultsmentioning

confidence: 99%

One pot spiropyrazoline synthesis via intramolecular cyclization/methylation

Dadiboyena

Hamme

2011

Tetrahedron Letters

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Regioisomeric spiropyrazolines were synthesized through a tandem intramolecular cyclization/methylation reaction of a functionalized 5,5-disubstituted pyrazoline in one reaction vessel. The 5,5-pyrazolines were constructed through a 1,3-dipolar cycloaddition reaction of aromatic ring containing nitrile imines and a disubstituted geminal alkene. An evaluation of the relative location of the nucleophilic and electrophilic functional groups on the pyrazoline was performed in order to ascertain the best pyrazoline system for the intramolecular cyclization/methylation reaction. Higher spiropyrazoline isolated yields were realized from pyrazolines with the electrophilic ester located further away from the pyrazoline when compared to pyrazolines with a directly bonded ester.

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Section: Resultsmentioning

confidence: 99%