Über Chlormethylverbindungen. I. Zur Synthese von Poly‐chlormethyl‐toluolen

Drechsler, Gerhard

doi:10.1002/prac.19630190507

J. Prakt. Chem.

1963

DOI: 10.1002/prac.19630190507

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Über Chlormethylverbindungen. I. Zur Synthese von Poly‐chlormethyl‐toluolen

Gerhard Drechsler

Abstract: Es wird über die Darstellung von 13 Poly‐chlormethyl‐toluolen berichtet, von denen 11 bisher unbekannt waren. Die Konstitutionen der neuen Verbindungen wurden, soweit möglich, aufgeklärt.

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Synthesis of 2,4‐diamino‐9H‐indeno[2,1‐d]pyrimidines

Rosowsky

Dey

Battaglia

et al. 1969

Journal of Heterocyclic Chem

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As part of a search for new antifolic, antimalarial, and antitumor agents, a series of 2,4-diamino-9H-indeno[2,1d]pyrimidines was prepared by condensation of guanidine with substituted 2-alkoxy-3-cyano-lKindenes. Base-catalyzed cyclization of 1,2-bis(cyanomethyl)benzenes afforded 2-amino-3-cyano-lH-indenes, which were converted into 3-cyano-2-methoxy-Uindenes by acid hydrolysis and treatment of the resultant 1-cyano-2-indanones with diazomethane. Alternatively, 2-amino-3-cyano-M-indenes could be transformed directly into 2-ethoxy-3-cyano-M-indenes by reaction with ethanol and sulfuric acid. The 2,4diamino-9H-indeno[2,1-d]pyrimidines represent a new type of planar, tricyclic pyrimethamine analog, in which free rotation of the phenyl and pyrimidine rings is prevented by means of a methylene bridge.As part of a larger chemical and biological program involving polycyclic 2,4-diaminopyrimidines (2), we recently reported the synthesis (3-5) and growth-inhibitory properties (6) of 1,3-diaminobenzolf ]quinazolines (I, X = -CH=CH-) and 1,3-diamino-5,6-dihydrobenzolflquinazolines (I, X = -CH2CH2-). These tricyclic systems are of considerable interest as structural analogs of pyrimethamine (11), a well-known antifolic agent which has been used clinically for a number of years in the treatment of malaria (7). Additional interest in these analogs was provided by the experimental antitumor activity reported for the closely related 2,4diamino-5-(3',4'-dichlorophenyl)-6-methylpyrimidine (111) (8). I 11 R = CH,, R = 4'43 111 R' = H, R = 3', 4'-C1,

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Synthesis of 2,4‐diamino‐9H‐indeno[2,1‐d]pyrimidines

Rosowsky

Dey

Battaglia

et al. 1969

Journal of Heterocyclic Chem

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Über Chlormethylverbindungen, III. Zur Papierchromatographie von Chlormethylverbindungen

Drechsler

1963

J. Prakt. Chem.

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Chlormethylverbindungen lassen sich nach Umsetzung mit Piperidin oder anderen entsprechenden sekundären Aminen papierchromatographisch trennen. Die Leistungsfähigkeit der Methode wird am Beispiel der Untersuchung von Reaktionsgemischen, die bei der Darstellung von Poly‐chlormethyl‐toluolen(1) erhalten wurden, dargelegt. Aus den RF‐Werten der Umsetzungsprodukte aller bekannten Chlormethyltoluole mit Piperidin ergeben sich interessante Beziehungen zwischen RF‐Wert und Konstitution.

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Über Chlormethylverbindungen. IV. Zur Synthese von Bis‐hydroxymethyl‐toluolen und ihren Derivaten

Drechsler

Zwintzscher

1964

J. Prakt. Chem.

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Über Chlormethylverbindungen. I. Zur Synthese von Poly‐chlormethyl‐toluolen

Abstract: Es wird über die Darstellung von 13 Poly‐chlormethyl‐toluolen berichtet, von denen 11 bisher unbekannt waren. Die Konstitutionen der neuen Verbindungen wurden, soweit möglich, aufgeklärt.

Cited by 4 publications

References 4 publications

Synthesis of 2,4‐diamino‐9H‐indeno[2,1‐d]pyrimidines

Synthesis of 2,4‐diamino‐9H‐indeno[2,1‐d]pyrimidines

Über Chlormethylverbindungen, III. Zur Papierchromatographie von Chlormethylverbindungen

Über Chlormethylverbindungen. IV. Zur Synthese von Bis‐hydroxymethyl‐toluolen und ihren Derivaten

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