Accessing Extended Fused Isoindolinones Via Sequential Anionic Intramolecular Cyclizations.

Area of Science:

• Organic Chemistry
• Heterocyclic Chemistry
• Synthetic Chemistry

Background:

• Fused heterocyclic frameworks are crucial in medicinal chemistry and materials science.
• Developing efficient synthetic routes to complex heterocyclic systems remains a significant challenge.

Purpose of the Study:

• To introduce a novel strategy for synthesizing unusual fused heterocyclic frameworks.
• To explore the scope and regioselectivity of sequential anionic intramolecular cyclizations.

Main Methods:

• Employed sequential anionic intramolecular cyclizations for framework construction.
• Utilized computational modelling to understand and predict reaction outcomes.
• Investigated 5-Exo-dig, 6-exo-dig, and 7-endo-dig cyclization pathways.

Main Results:

• Achieved excellent yields of target fused heterocyclic frameworks.
• Successfully synthesized isoindolinone, fused isoquinoline, and azepine motifs.
• Demonstrated regioselectivity control through stereoelectronic effects (n_C- →π*_(Ph) interactions).

Conclusions:

• Established a versatile and efficient method for accessing complex fused heterocycles.
• Highlighted the importance of stereoelectronic effects in directing cyclization regioselectivity.
• Computational modelling provided valuable insights into the reaction scope and mechanism.