A Facile Synthesis of Substituted Indenones and Piperidine‐2,6‐diones from the Baylis–Hillman Acetates

Abstract

Baylis–Hillman acetates were conveniently transformed into substituted indenone and piperidine‐2,6‐dione frameworks by treatment with (di)phenylacetonitrile followed by Friedel–Crafts cyclization or imide formation.

Baylis–Hillmanadducts as an important synthon for the synthesis of α‐carbolinone and α‐carboline derivatives

“…The presented protocol involves three step reactions, that is (1) monoalkylation of 2‐nitrobenzylcyanide, (2) imide formation/Friedel–Crafts cyclization, and (3) reduction of nitro group followed by cyclization to the formation of tricyclic‐heterocyclic compounds, α‐carbolinone derivatives or tetra/pentacyclic‐heterocyclic compounds, α‐carboline derivatives (Scheme 1). Basavaiah et al [8a] successfully used B‐H adducts 1 ( tert ‐butyl 3‐acetoxy 2‐methylene‐3‐arylpropanoates) for the synthesis of substituted imide derivatives. They extended the methodology for the synthesis of substituted indenone derivatives via Friedel–Craft cyclization reaction.…”

“…They extended the methodology for the synthesis of substituted indenone derivatives via Friedel–Craft cyclization reaction. They also reported, Johnson–Claisen rearrangement product of 3‐(2‐nitroaryl)‐3‐hydroxy‐2‐methylenepropanenitrile (B‐H adducts) through reductive cyclization protocol of nitro, nitryl, and ester groups for the synthesis of tricyclic compouds [8b]. Having this background we envisioned that mono‐alkylated B‐H adduct ( 2 ) containing nitro, nitryl, and ester groups can be transformed into α‐carbolinone ( 5 ) derivatives.…”

High throughput selection of organic cathode materials

“…In general, these systems lack stability, and their reduction potential can go up to 5.88 V for the molecule 39. Among them, 2-indenone derivatives are the most stable isomers 120,121 due aromatic stabilization 81 Again, the absence of the (thio)carbonyl group reduces the reduction potential from 5.20 (40) to 3.92 V of the corresponding purine (41). Both 42 and 43 are expected to be stable, 122,123 although the increase in molecular weight yield lower energy densities.…”

The Solid-State Structures of Cyclic NH Carboximides

“…Seven structures have been reported for tetra-and penta-substituted glutarimides. Five structures-compounds 226 [194], 227 [195], 228 [180], 229 [196] and 230 [196] (Figure 69) exist as simple R 2 2 (8) dimers of category A. The compounds 231 [196] and 232 [196] exist as linear C( 6) chains of imide NH to remote CN nitrogen hydrogen bonding of pattern E.…”