Unexpected Rearrangements of Bicyclic Pyrazolines Derived from 6,6-Diphenylpentafulvene

Djapa, Francis; Msaddek, Moncef; Ciamala, Kabula; Vebrel, J.; Riche, C.

doi:10.1002/1099-0690(200004)2000:7<1271::aid-ejoc1271>3.0.co;2-o

Cited by 5 publications

(1 citation statement)

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“…Except for a few isolated and unclear literature reports, the dipolar reactivity of diphenylnitrilimine with pentafulvenes was not studied prior to 2000 . In early 2000, Ciamala et al have demonstrated the [3+2] dipolar cycloaddition reactions of diphenylpentafulvene with various diarylnitrilimines 194 , leading to regioisomeric pyrazoline derivatives . They have also given the details of the acid promoted intramolecular rearrangement of the cycloadducts into substituted quinoline and pyrazole derivatives (Scheme ).…”

Section: Cycloaddition Chemistry Of Pentafulvenesmentioning

confidence: 99%

Recent Advances in the Chemistry of Pentafulvenes

et al. 2017

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Pentafulvenes are a unique class of compounds that originally attracted attention due to their propensity to display nonbenzenoid aromaticity. Subsequently, they were recognized as valuable synthons for the construction of a wide range of compounds by virtue of their ability to display multiple cycloaddition profiles. Naturally, this area of organic chemistry has experienced rapid growth over the last five decades, fueled by elegant work showcasing the unique reactivity of pentafulvenes in a plethora of cycloaddition reactions. In this Review, we have attempted to provide a systematic account of the methods for the generation of pentafulvenes, their rich and varied cycloaddition chemistry, organometallic reactions, and theoretical studies that support their versatility. Further, we have highlighted their applications in the synthesis of a variety of complex structural frameworks. It is our conviction that this Review will be useful to a wide range of chemists, and will spur further research in this promising area.

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Section: Cycloaddition Chemistry Of Pentafulvenesmentioning

confidence: 99%