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Volumn 35, Issue 4, 1998, Pages 787-793

Ring Transformations of Heterocyclic Compounds. XVI [1]. Spiro[cyclohexadiene-dihydroacridines]. A Novel Class of Spirodihydroacridines by Ring Transformation of Pyrylium Salts with 9-Methylacridine and its Quaternary Salts

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EID: 0000667738     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570350403     Document Type: Article
Times cited : (2)

References (49)
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    • For the classification of pyrylium ring transformations see reference [2a].
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    • note
    • A careful analysis of the crude products obtained in the transformation 1 + 2a → 3 by thin layer chromatography (Silufol® tlc-plates, eluent: n-hexane:acetone = 2:1 [v:v]) showed that in all reactions traces of N-demethylated spiro[cyclohexadiene-dihydroacridines] were formed as by-products; they could easily be removed by recrystallization from ethanol/toluene.
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    • For other dealkylations of acridinium salts of the type 2 by melting or during reactions see: A. Bernthsen, Liebigs Ann. Chem., 224, 20 (1884); T. V. Stupnikova, B. P. Zemskii, Yu. B. Vysotskii, R. S. Sagitullin, and Kh. Ya. Lopatinskaya, Khim. Geterotsikl Soedin., 7, 959 (1980); S. Tamagaki, M. Ueno, and W. Tagaki, Bull. Soc. Chim. Japan, 65, 55 (1992); K. Papadopoulos, J. Nikokovonras, and D. Dimotikali, J. Prakt. Chem./Chem.-Ztg, 336, 506 (1994).
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    • For other dealkylations of acridinium salts of the type 2 by melting or during reactions see: A. Bernthsen, Liebigs Ann. Chem., 224, 20 (1884); T. V. Stupnikova, B. P. Zemskii, Yu. B. Vysotskii, R. S. Sagitullin, and Kh. Ya. Lopatinskaya, Khim. Geterotsikl Soedin., 7, 959 (1980); S. Tamagaki, M. Ueno, and W. Tagaki, Bull. Soc. Chim. Japan, 65, 55 (1992); K. Papadopoulos, J. Nikokovonras, and D. Dimotikali, J. Prakt. Chem./Chem.-Ztg, 336, 506 (1994).
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