Next Article in Journal
An Effective Microwave-Induced Iodine-Catalyzed Method for the Synthesis of Quinoxalines via Condensation of 1,2-Diamines with 1,2-Dicarbonyl Compounds
Previous Article in Journal
Rhodium-Catalyzed Linear Codimerization and Cycloaddition of Ketenes with Alkynes
Molecules 2010, 15(6), 4201-4206; doi:10.3390/molecules15064201
Article

Synthesis of 2-(9,10-Dihydro-9,10-propanoanthracen-9-yl)-N-methylethanamine via a [4+2] Cycloaddition

* , ,  and
Received: 19 May 2010 / Revised: 31 May 2010 / Accepted: 1 June 2010 / Published: 9 June 2010
Download PDF [126 KB, uploaded 18 June 2014]

Abstract

The synthesis of the tetracyclic molecule 2-(9,10-dihydro-9,10-propano-anthracen-9-yl)-N-methylethanamine(2)as a homologue of the antidepressant 1-(9,10-dihydro-9,10-ethanoanthracen-9-yl)-N-methylmethaneamine (1) was described. The key intermediate 9-(prop-2-en-1-yl)-9,10-dihydro-9,10-propanoanthracen-12-one (7)was successfully synthesized via a [4+2] cycloaddition of α-bromoacrolein and 9-allyl-anthracene, followed by ring expansion and samarium diiodide deoxygenation.
Keywords: benzoctamine; homologue; antidepressant; ring expansion; cycloaddition benzoctamine; homologue; antidepressant; ring expansion; cycloaddition
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote
MDPI and ACS Style

Karama, U.; Al-Saidey, A.; Al-Othman, Z.; Almansour, A.R. Synthesis of 2-(9,10-Dihydro-9,10-propanoanthracen-9-yl)-N-methylethanamine via a [4+2] Cycloaddition. Molecules 2010, 15, 4201-4206.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

Cited By

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert