Synthesis of dibenzo[a,d]cycloheptanoids via aryne insertion into 2-arylidene-1,3-indandiones
Nagaraju Payili1, Santhosh Reddy Rekula, Anjaiah Aitha
1Chemistry Services, GVK Biosciences Pvt. Ltd, Survey Nos: 125 (part) & 126, IDA Mallapur, Hyderabad 500076, Telangana, India. satya@gvkbio.com.
Abstract:
A novel and unexpected aryne insertion cascade reaction on 2-arylidene-1,3-indandiones via conjugate addition of fluoride followed by formal C-C insertion is developed to afford dibenzo[a,d]cycloheptanoid derivatives in good yields with a single isomer. This reaction represents a rare instance of cyclic enone C-C bond insertion (acyl-alkenylation) in aryne chemistry. Interestingly, 2-arylidene-1,3-indandiones bearing electron rich functional groups provided dibenz[a,c]anthracene-9,14-dione derivatives via [4 + 2] cycloaddition followed by ring expansion.
More Related Videos
14:11Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
11:45Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Cycloaddition Reactions: Overview
