Related Experiment Video
Updated: Jul 6, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Direct Spirocyclization of Tryptamines with Dearomatized Phenols Enables Catalyst-Free Access to C3-Spirocyclic
Rima Samanta1, Rina Mahato1, Vigneshwaran V2
1Department ofChemistry, Indian Institute ofTechnology Delhi, New Delhi 110016, India.
This study introduces a novel fluorinated alcohol method for synthesizing spirocyclic indolenines from tryptamines. This catalyst-free approach efficiently creates complex molecules with broad applicability and high yields.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Tryptamine derivatives are crucial scaffolds in medicinal chemistry.
- Efficient synthesis of complex spirocyclic structures remains a challenge.
Purpose of the Study:
- To develop a regioselective spirocyclization strategy for tryptamines.
- To synthesize C3-spirocyclic indolenines with all-carbon quaternary centers.
Main Methods:
- Fluorinated alcohol-mediated reaction of tryptamines.
- Catalyst-free protocol.
- Density functional theory (DFT) calculations for mechanistic insights.
Main Results:
- Achieved efficient synthesis of C3-spirocyclic indolenines.
- Demonstrated broad substrate scope and high functional-group tolerance.
- Identified ketimine intermediate and confirmed C3 cyclization preference via DFT.
Conclusions:
- The developed method offers a practical and versatile route to valuable spirocyclic indolenines.
- Gram-scale synthesis validates the methodology's utility for further transformations.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
07:12Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Related Concept Videos
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3