Poly-yne Cyclization at Mild Temperatures

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Solution Overview

Problem

Current methods for preparing cyclic compounds, especially polycyclic ring systems, often require harsh conditions that can damage sensitive functionalities and are not efficient for highly substituted systems, limiting their application in fields like pharmaceuticals and electronics.

Innovation Solution

A mild method involving the cyclization of poly-yne compounds at temperatures below 300°C, allowing for the formation of polycyclic compounds through intermolecular cyclization of compounds with multiple alkyne groups, either directly or with the aid of a template, to create complex cyclic structures without damaging sensitive functionalities.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional cyclization methods are used to prepare cyclic compounds, then cyclic ring systems can be formed, but harsh conditions damage sensitive functionalities

Engineering Contradiction:
Improvecyclization method applicabilityVSAvoiddamage to sensitive functionalities
Core Design Contradiction:
Ease of manufactureVSObject-affected harmful factors

Solution Approach 1:

The patent changes the temperature parameter from conventional high temperatures to below 300°C, and modifies the chemical environment by using specific catalysts and solvents, enabling cyclization under milder conditions that preserve sensitive functional groups while still achieving effective ring formation

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces intermediates such as metal complexes and catalytic species that facilitate the cyclization process at lower temperatures, allowing the reaction to proceed through alternative pathways that avoid the harsh conditions normally required

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If conventional cyclization methods are used, then cyclic compounds can be prepared, but the conditions are not mild enough for complicated ring systems

Engineering Contradiction:
Improvepreparation efficiencyVSAvoidreaction temperature
Core Design Contradiction:
ProductivityVSTemperature

Solution Approach 1:

The patent replaces thermal energy input with catalytic mechanisms, where metal complexes and other catalysts lower the activation energy barrier, allowing cyclization to occur at below 300°C instead of requiring high temperatures, thus maintaining productivity while reducing thermal stress on the system

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

3Manufacturing precision

If conventional methods are used for highly substituted cyclic ring systems, then ring formation can occur, but the methods are not efficient

Engineering Contradiction:
Improvesubstitution pattern controlVSAvoidsynthesis efficiency
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent segments the cyclization process into controlled stages using modular building blocks with pre-positioned functional groups, allowing stepwise construction of highly substituted ring systems with precise control over substitution patterns while maintaining overall synthesis efficiency through the use of common intermediates

Inventive Principle:
Principle #1Segmentation

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

This method enables the efficient preparation of a wide array of cyclic compounds under mild conditions, preserving sensitive functionalities and allowing for the synthesis of complex polycyclic structures useful in various industries, including pharmaceuticals and electronics.

Implementation Method 1

cyclizing a tri-yne compound at a temperature below about 300° C. to provide a polycyclic compound

Methodology Applied
Scientific EffectThermal cyclization: Thermolysis

Data Source

PatentUS9505789B2Cyclization methods
Publication Date: 2016.11.29 REGENTS OF THE UNIVERSITY OF MINNESOTA
  • US9505789B2 patent drawing
  • US9505789B2 patent drawing
  • US9505789B2 patent drawing

AI summary

The invention provides methods for cyclizing poly-yne compounds under mild conditions to provide cyclic compounds.