Synthetic routes to benzosuberone-based fused- and spiro-heterocyclic ring systems

Abstract

Benzosuberones are an important class of medicinal and pharmaceutical compounds and have recently attracted considerable attention. The present review highlights the progress in the synthesis of benzosuberones and their fused and spiro ring systems up to 2015.

Palladium‐catalyzed domino reaction for the synthesis of benzo‐cyclohepta‐quinolinone analogues from Cedrus deodara oil

“…Silica gel (60-120 mesh size) for column chromatography was procured from Sd Finechem Ltd. Commercial reagents and solvents were of analytical grade and were purified by standard procedures prior to use. All the reactants were prepared by F I G U R E 1 Some biologically significant benzocycloheptene analogues 1 S C H E M E 1 Outline of previous and present approaches 11,12 using Anton Paar monomode microwave 200 instruments. Reactions were monitored by thin-layer chromatography (TLC) plates coated with 0.2 mm silica gel 60 F 254 .…”

“…The viscous liquid obtained was purified by column chromatography on silica gel (mesh 60-120) using the mixture of Hexane: EtOAc (80:20) to obtained the desired product 5a as semisolid (25 mg, 60%). 1…”

“…Benzocycloheptene is an important structural motif embedded in several natural products such as Colchicine, Allocolchicine, and Bussealine E that are clinically reported to exhibit anti‐tumor activity (Figure 1). 1 Over the years, the various structural analogues of benzocycloheptene have attracted considerable attention from chemists owing to their remarkable properties as biologically potent compounds as well as in material and medicinal chemistry 3 . Quinolone class of compounds is also well known for their therapeutic applications such as anti‐bacterial, anti‐virulence, anti‐biofilm, and anti‐viral activities 2 .…”

Bis‐thiourea Derivatives and Their Utility in Synthesis of Mono‐heterocyclic, Bis‐heterocyclic, and Fused Heterocyclic Systems

“…Some bis‐thiourea derivatives were also applied as anion selective fluorescent chemosensors , and some had enantiomeric recognition ability . As part of our research work towards utilization of thiourea derivatives in synthesis of various heterocycles with broad biological activities , in this review article, the synthetic routes towards bis‐thiourea as well as their applications in synthesis of various classes of heterocyclic systems are extensively surveyed.…”

Synthesis of Benzo-Fused Cyclic Ketones via Metal-Free Ring Expansion of Cyclopropanols Enabled by Proton-Coupled Electron Transfer

“…1-Tetralones and 1-benzosuberones are broadly found in natural products such as Hamigeran A, Merochlorin B, and Parviflorol (Figure a) . In addition, they have been used as versatile building blocks in the synthesis of complex molecules . Accordingly, considerable effort has been devoted to achieve efficient construction of these benzo-fused ketone frameworks. − However, metal-free catalytic methods for the synthesis of 1-tetralones and 1-benzosuberones bearing substituents at the benzylic position are underdeveloped …”