Phenanthrene: A Versatile Molecule; A Review

Abstract

Phenanthrene is a nucleus of the poly aromatic hydrocarbon family consisting of three fused benzene rings. They are of great importance in the field of medicine. They are mainly synthesized through Bardhan-Sengupta synthesis, Haworth synthesis and Pschorr synthesis of phenanthrene. Presently, many naturally existing drugs such as morphine, codeine halofantrine, among others bear the phenanthrene nucleus. Synthetic derivatives including dextromethorphan and other drugs also possess this nucleus. Phenanthrene derivates have many distinct therapeutic benefits including analgesic, antitussive, antimalarial, cytotoxic, and anticonstipation. This study was performed to highlight the various pharmacological uses of phenanthrene derivatives by reviewing experiments performed on its derivatives.

Radical-mediated sulfonylative/thiolative cyclization of biaryl enones to phenanthrone derivatives

“…Beyond the scalability, the synthetic potential could be further emphasised by the adaptable downstream conversions of the product into valuable structural motifs of bioactive natural products. 1 For instance, compound 4b could be easily decarbonylated to obtain 9,10-dihydrophenanthrene 7 (74%) using polymethyl-hydrosiloxane (PMHS) in the presence of B(C 6 F 5 ) 3 (Scheme 5b). 14 Reduction of 4b in the presence of NaBH 4 in MeOH provided the corresponding dihydrophenanthren-9-ol 8 in 83% yield (Scheme 5c).…”

“…1). 1 Additionally, they also serve as functional materials in organic light emitting devices (OLEDs), precisely phenanthrones bearing all carbon quaternary centers in which the ketone functionality is analogous to the carbonyl of fluorenone. 2 Given their significant potential, the direct construction of phenanthrones bearing a quaternary carbon is challenging and draws the attention of synthetic organic chemists.…”

Pd-catalyzed regioselective rollover dual C–H annulation cascade: facile approach to phenanthrene derivatives

“…10 a As a contribution to these cryptic reactive patterns of substituted phenols, we 11 herein showed an unprecedented reactivity of o -aryl phenols for the cascade regioselective rollover annulation with hydroxyl alkynoates for constructing phenanthrene cores with extended conjugation, a distinct class of polyaromatic hydrocarbons (PAHs) with remarkable application potential in the areas of medicinal and material chemistry. 12 Chelation of OH group with palladium was the key in controlling the regioselectivity.…”