Ring transformations of heterocyclic compounds. XVI. Spiro[cyclohexadiene‐dihydroacridines]. A novel class of spirodihydroacridines by ring transformation of pyrylium salts with 9‐methylacridine and its quaternary salts
- 1 July 1998
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 35 (4), 787-793
- https://doi.org/10.1002/jhet.5570350403
Abstract
2,4,6‐Triarylpyrylium salts 1 react with the in situ generated anhydrobase of 9,10‐dimethylacridinium methosulfate (2a) in the presence of anhydrous sodium acetate in ethanol by a 2,5‐[C4+C2] pyrylium ring transformation to give the hitherto unknown 6‐aroyl‐3,5‐diaryl‐10′‐methylspiro[cyclohexa‐2,4‐diene‐1,9′‐9′,10′‐dihydro‐acridines] 3. When the pyrylium perchlorate 1a is treated under the same conditions with the N‐ethyl, N‐allyl or N‐benzyl substituted acridinium salts 2b‐d a dealkylation of these salts occurs and the N‐unsubstituted spiro[cyclohexadiene‐dihydroacridine] 4a is formed. The same compounds 4 can also be obtained by transformation of the pyrylium salts 1 with 9‐methylacridine (7) and triefhylamine/acetic acid in ethanol. Structure elucidation is performed by an X‐ray crystal structure determination of the spiro[cyclohexadiene‐dihydroacridine] 3a. Spectroscopic data of the transformation products and their mode of formation are discussed.This publication has 25 references indexed in Scilit:
- Photochromism of a Novel Class of Spiroindolines: 6-Aroyl-3,5-diarylspiro[cyclohexa-2,4-diene-1,2‘-indolines]The Journal of Physical Chemistry A, 1997
- Ring transformations of heterocyclic compounds. XIV. Ring transformations of pyrylium and thiopyrylium salts with anhydro‐bases derived from 1H‐benzimidazolium and benzothiazolium salts: An easy access to 2‐(2,4,6‐triarylphenyl) 1H‐benzimidazolium and benzothiazolium derivativesJournal of Heterocyclic Chemistry, 1996
- Ring transformations of heterocyclic compounds. XIII. Bis(2,4,6‐triarylphenyl) substituted bispyridinium salts from methyl derivatives by double pyrylium and thiopyrylium ring transformationsJournal of Heterocyclic Chemistry, 1996
- Ring transformations of heterocyclic compounds. XI. 2,4,6‐triarylphenylquinolinium salts from methyl substituted derivatives via (thio)pyrylium ring transformationsJournal of Heterocyclic Chemistry, 1995
- Ring transformations of heterocyclic compounds. X. A simple method for the conversion of methyl substituted pyridinium salts into 2,4,6‐triarylphenyl derivatives: The first (thio)pyrylium ring transformations with heterocyclic anhydrobases as carbon nucleophilesJournal of Heterocyclic Chemistry, 1995
- Ringtransformationen heterocyclischer Verbindungen. XII. Neuartige Spiroindoline via Ringtransformation von 2,4,6-Triaryl-pyryliumsalzen mit 2-Methylen-indolinenAdvanced Synthesis & Catalysis, 1995
- Reactions of Lucigenin in protic solvents in the presence of aminesAdvanced Synthesis & Catalysis, 1994
- The Reaction of a 10-Methylacridinium Salt with Tertiary AminesBulletin of the Chemical Society of Japan, 1992
- Pyryliumverbindungen. XXI. Struktur und Tautomerie von Pseudobasen unsymmetrisch substituierter 2,4,6‐TriarylpyryliumsalzeJournal für Praktische Chemie, 1984
- Über ein einfaches Verfahren zur Darstellung von TriarylpyryliumsalzenHelvetica Chimica Acta, 1956