Related Experiment Video
Updated: May 23, 2025

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
Expanding Diversity of Fused Steroid-Quinoline Hybrids by Sequential Amination/Annulation/Aromatization Reactions
Caterina Momoli1, Antonio Arcadi1, Marco Chiarini2
1Dipartimento di Scienze Fisiche e Chimiche, Università degli studi dell'Aquila, Via Vetoio, Coppito (AQ), 67100 L'Aquila,Italy.
Abstract:
Viable alternative approaches to a variety of ring A and ring D-fused steroid-quinoline hybrids, along with ring A, D-fused, and/or ring A-fused, side chain-substituted steroid-bis-quinolines were explored by means of sequential amination/annulation/aromatization reactions of suitable ketosteroids with 2-acyl-substituted anilines. Key factors directing the chemoselective behavior of polyfunctionalized substrates were investigated. Remarkably, the use of TMSOTf as an alternative promoter/catalyst enabled the direct synthesis of the desired hybrids, avoiding the protection/deprotection steps of the conventional procedures when the starting substrates contained labile functional groups.
Related Concept Videos
Cycloaddition Reactions: Overview
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nucleophilic Aromatic Substitution: Elimination–Addition
Preparation of Amines: Alkylation of Ammonia and Amines
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

![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)