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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.7K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.4K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

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Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
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Curcumin-based bioactive heterocycles derived via multicomponent reactions.

Amol A Nagargoje1,2, Mubarak H Shaikh1,3, Bapurao B Shingate1

  • 1Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, Maharashtra, India.

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Summary

This review explores multicomponent reactions (MCRs) using curcuminoids to synthesize novel curcumin-based heterocycles. These compounds exhibit diverse pharmacological activities, highlighting curcumin

Keywords:
Biginelli reactionHantzsch reactioncurcumin-based heterocyclesmulticomponent reactionspharmacological activities

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Natural Products Chemistry

Background:

  • Curcumin, a phytochemical from South Asia, is a versatile starting material.
  • Multicomponent reactions (MCRs) offer efficient pathways for synthesizing complex molecules.
  • Curcumin-based heterocycles are of significant interest in drug discovery.

Purpose of the Study:

  • To review recent advances (last 10 years) in synthesizing curcumin-based heterocycles using MCRs.
  • To highlight the role of curcuminoids as key reactants in these MCRs.
  • To discuss the pharmacological potential of the synthesized heterocyclic compounds.

Main Methods:

  • Focus on literature published within the last decade.
  • Analysis of MCRs employing curcuminoids.
  • Compilation of synthesized curcumin-based heterocycles and their reported activities.

Main Results:

  • Demonstration of MCRs as a powerful tool for generating diverse curcuminoid-derived heterocycles.
  • Identification of various pharmacological activities associated with these novel compounds.
  • Synthesis of complex heterocyclic scaffolds from readily available curcuminoids.

Conclusions:

  • MCRs provide an efficient and versatile strategy for accessing curcumin-based heterocycles.
  • These heterocycles hold promise for various therapeutic applications.
  • Further research into curcuminoid-based MCRs is warranted for drug development.