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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Published on: February 6, 2019

Trezimides and tennimides: new imide-based macrocycles.

Pavle Mocilac¹, John F Gallagher

¹School of Chemical Sciences, Dublin City University, Dublin 9, Ireland.

The Journal of Organic Chemistry

|February 5, 2013

Summary

Researchers synthesized novel macrocyclic imides, specifically "3 + 3" cyclic trimers (trezimides) and tetramers (tennimides), from isophthaloyl dichloride and aminopyridines/aminopyrimidines. These molecules exhibit distinct asymmetric conformations and channel dynamics in the solid state.

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Area of Science:

Supramolecular Chemistry
Organic Synthesis
Crystal Engineering

Background:

Macrocyclic compounds are crucial in supramolecular chemistry, with applications in host-guest chemistry and materials science.
Imide-based macrocycles offer unique structural and functional properties due to their rigid framework and hydrogen bonding capabilities.

Purpose of the Study:

To synthesize and characterize new imide-based macrocyclic trimers (trezimides) and tetramers (tennimides).
To investigate the conformational behavior and solid-state structures of these novel macrocycles.

Main Methods:

Reaction of isophthaloyl dichloride with 2-aminopyridine and 2-aminopyrimidine.
Single-crystal X-ray diffraction analysis to determine solid-state structures and conformations.
Analysis of conformational flexibility and pore dynamics in the solid state.

Main Results:

Successful synthesis of a new class of "3 + 3" macrocyclic trimers (trezimides) alongside known tetramers (tennimides).
Trezimides adopt distinct asymmetric conformations ((P) and (R)) in the solid state.
Tennimide structures reveal multiple conformational states with varying channel (pore) openness (cc/oc/oo).

Conclusions:

Macrocycle formation is influenced by the nucleophilicity of the aminopyridine/pyrimidine, the preorganized imide hinge, and isophthaloyl group flexibility.
The study highlights the conformational diversity and dynamic behavior of imide-based macrocycles in the solid state.