Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure
Open Access
- 7 October 2021
- journal article
- research article
- Published by Beilstein Institut in Beilstein Journal of Organic Chemistry
- Vol. 17 (1), 2511-2519
- https://doi.org/10.3762/bjoc.17.168
Abstract
A convenient and simple protocol has been developed for the synthesis of a series of new tetracyclic tetrahydroisoquinoline derivatives, 7,12-dihydro-6,12-methanodibenzo[c,f]-azocine-5-carboxylic acids by three component Petasis reaction with the use of aminoacetaldehyde acetals bearing substituted benzyl groups as the amine components followed by Pomeranz–Fritsch double cyclization reaction. By applying this method, several acids have been prepared in satisfactory yields. An unprecedented chemical behavior of a Petasis reaction product in diluted HCl solution leading to the formation of a phenylglycine derivative has been observed and the mechanism explaining such reactivity has been proposed.Keywords
Funding Information
- Narodowe Centrum Nauki (NCN) Polish National Science Centre (2011/01/D/ST5/06627)
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