Related Experiment Video
Updated: Sep 12, 2025
![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
Copper(I)-Catalyzed Skeletal Rearrangement-Driven Cycloisomerization of 1,11-Diynes
Jin-Qi Zhang1, Qing-Mei Li1, Shi-Lang Chen1
1Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Guangxi Key Laboratory of Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, China.
Abstract:
Herein, we report a copper(I)-catalyzed skeletal rearrangement-driven cycloisomerization of 1,11-diynes under a mild reaction. This method adopts O-propargyl oxime-containing 1,11-diynes and provides efficient access to functionalized chromeno[4,3-b]pyrroles in high yields and high regioselectivity. Mechanistic studies revealed that the cycloisomerization of 1,11-dynes underwent copper-catalyzed [2,3] rearrangement, sequential [3 + 2] cycloaddition, and [3,3] rearrangement in a one-pot reaction. Diverse derivations of the cycloisomerization products have also been demonstrated. The present method features a broad substrate scope and good functional group tolerance, two ring and five C-C/C-N/C-O bond formation, and the first example of cycloisomerization of 1,11-diynes.
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
07:56Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
Published on: August 12, 2019
Related Concept Videos
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: Overview
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Thermal Electrocyclic Reactions: Stereochemistry
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.