Two robust, efficient syntheses of [phenyl ring-U-14C]indole through use of [phenyl ring-U-14C]aniline

Two robust, efficient syntheses of [phenyl ring‐U‐14C]indole are presented. In the first synthesis, we developed optimum reaction conditions for the Houben–Hoesch alkylation of chloro acetonitrile with aniline. This was found through the screening of several Lewis acids coupled with the use of Sugas...

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Bibliographic Details
Published in:Journal of labelled compounds & radiopharmaceuticals 2006-06, Vol.49 (7), p.615-622
Main Authors: Wager, Carrie A. B., Miller, Sandra A.
Format: Article
Language:English
Subjects:
aniline
Chemistry
directed acylation
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Houben-Hoesch
indole
microwave
Organic chemistry
Preparations and properties
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Summary:Two robust, efficient syntheses of [phenyl ring‐U‐14C]indole are presented. In the first synthesis, we developed optimum reaction conditions for the Houben–Hoesch alkylation of chloro acetonitrile with aniline. This was found through the screening of several Lewis acids coupled with the use of Sugasawa conditions for ortho direction. Following alkylation, the resultant imine was hydrolyzed to the phenone, and then thermal cyclization followed by reduction led to indole. In the second synthesis of [phenyl ring‐U‐14C]indole, we utilized microwave‐enhanced conditions for the key coupling. In this transformation, aniline was alkylated with the acetal of bromo acetaldehyde. The mono‐alkylated aniline was then transformed in a straightforward manner to indole. Copyright © 2006 John Wiley & Sons, Ltd.
ISSN:0362-4803
1099-1344
DOI:10.1002/jlcr.1067