Issue 0, 1971
From the journal:

Journal of the Chemical Society C: Organic

Quinoline alkaloids. Part XI. A study of the Claisen rearrangement of the 3,3-dimethylallyl ether of 4-hydroxy-1-methyl-2-quinolone. Synthesis of ifflaiamine and the identification of a new alkaloid from Flindersia ifflaiana F. Muell

T. R. Chamberlain  and  M. F. Grundon  

Abstract

Claisen rearrangement of 1-methyl-4-(3-methylbut-2-enyloxy)2-quinolone resulted mainly in abnormal reaction to give a 1,2-dimethylallylquinoline and its linear and angular cyclisation products. The intermediate 1,1-dimethylallylquinoline was trapped as its acetate which was cyclised to ifflaiamine with hydrobromic acid. An isomeric furanoquinoline alkaloid is shown to occur with ifflaiamine in Flindersia ifflaiana and the biogenesis of the two alkaloids is discussed.

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/J39710000910
Article type
Paper

J. Chem. Soc. C, 1971, 910-914

Permissions

Request permissions

Quinoline alkaloids. Part XI. A study of the Claisen rearrangement of the 3,3-dimethylallyl ether of 4-hydroxy-1-methyl-2-quinolone. Synthesis of ifflaiamine and the identification of a new alkaloid from Flindersia ifflaiana F. Muell

T. R. Chamberlain and M. F. Grundon, J. Chem. Soc. C, 1971, 910 DOI: 10.1039/J39710000910

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements