Functionalised Cookson's Diketones in Chlorosulfonic Acid: Towards Polysubstituted D3-Trishomocubanes-Reference-Cited by-同舟云学术

Functionalised Cookson's Diketones in Chlorosulfonic Acid: Towards Polysubstituted D3-Trishomocubanes

Published:2017-12 Issue:12 Volume:41 Page:718-721
ISSN:1747-5198
Container-title:Journal of Chemical Research
language:en
Short-container-title:Journal of Chemical Research

Author:

Zhyhadlo Yevheniia Y.¹,Gaidai Alexander V.¹,Sharapa Dmitry I.²,Mitlenko Alena G.¹,Shishkin Oleg V.³,Shishkina Svitlana V.³,Levandovskiy Igor A.¹,Fokin Andrey A.¹

Affiliation:

1. Department of Organic Chemistry, Igor Sikorsky Kiev Polytechnic Institute, Prospekt Pobedy 37, 03056 Kiev, Ukraine

2. Computer-Chemie-Centrum and Interdisciplinary Center for Molecular Materials, University Erlangen-Nuremberg, Nagelsbachstrasse 25, 91052, Erlangen, Germany

3. Division of Functional Materials Chemistry, SSI ‘Institute for Single Crystals’, National Academy of Science of Ukraine, Lenina Avenue 60, Kharkov 61001, Ukraine

Abstract

A number of Cookson's diketone ( Cs-trishomocubane-8,11-dione) derivatives were synthesised and introduced into the reaction with chlorosulfonic acid to give previously unknown polysubstituted D3-trishomocubanes (pentacyclo[6.3.0.02,6.03,10.05,9]undecanes) – chiral analogues of the parent cubanes. In the case of 1,9-dibromo- Cs-trishomocubane-8,11-dione, the reaction proceeded with conservation of both carbonyl groups selectively affording 3-bromo-6-chloro- D3-trishomocubane-4,7-dione whose distinct substitution pattern was confirmed by means of X-ray structural analysis.

Publisher

SAGE Publications

Subject

General Chemistry

Link

http://journals.sagepub.com/doi/pdf/10.3184/174751917X15125690124264

Reference20 articles.

1. Pharmaceuticals that contain polycyclic hydrocarbon scaffolds

2. Application of the Bicyclo[1.1.1]pentane Motif as a Nonclassical Phenyl Ring Bioisostere in the Design of a Potent and Orally Active γ-Secretase Inhibitor

3. Cubanes: Starting Materials for the Chemistry of the 1990s and the New Century

4. Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success

5. The Lipophilic Bullet Hits the Targets: Medicinal Chemistry of Adamantane Derivatives

Cited by 3 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Design and Synthesis of Cage Molecules as High Energy Density Materials for Aerospace Applications;ChemCatChem;2020-11-19

2. Synthesis of functionalized cage propellanes and D3-Trishomocubanes via the ring-closing metathesis and acid-promoted rearrangement;Tetrahedron;2019-01

3. Molecular Acrobatics in Polycyclic Frames: Synthesis of Functionalized D3-Trishomocubanes via the Rearrangement Approach;The Journal of Organic Chemistry;2018-05-17