Synthesis and antimalarial effects of 2‐(3,4‐dichloroanilino)‐7‐[[[(dialkylamino)alkyl]amino]]‐5‐methyl‐ s ‐triazolo[1,5‐ a ]pyrimidines | Zendy

Werbel Leslie M. | Zendy; Elslager Edward F. | Zendy; Chu Vera P. | Zendy

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Synthesis and antimalarial effects of 2‐(3,4‐dichloroanilino)‐7‐[[[(dialkylamino)alkyl]amino]]‐5‐methyl‐ s ‐triazolo[1,5‐ a ]pyrimidines

Author(s) -

Werbel Leslie M.,

Elslager Edward F.,

Chu Vera P.

Publication year - 1973

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570100435

Subject(s) - chemistry , ring (chemistry) , pyrimidine , hydrazine (antidepressant) , yield (engineering) , alkyl , acetic acid , nuclear magnetic resonance spectroscopy , 1,2,4 triazole , bicyclic molecule , medicinal chemistry , stereochemistry , organic chemistry , materials science , chromatography , metallurgy

3,4‐Dichlorophenylisothioeyanate ( 10 ) was allowed to react with 2‐methy1‐2‐thiopseudourea to give methyl 4‐(3,4‐dichlorophenyl)(dithioaltophanimidate ( 11 ) (41%), which upon treatment with hydrazine afforded 3‐amino‐5‐(3,4‐dichloroanilino)‐ s ‐triazole ( 12 ) (54‐91%). Ring‐closure with ethyl acetoacetale in acetic acid afforded 2‐(3,4‐dichloroanilino)‐5‐methyl‐ s ‐triazolo[ 1,5‐α ]‐pyrimidin‐7‐ol ( 13 ) (81%). Chlorination with phosphorus oxychloride gave 7‐chloro‐2‐(3,4‐dichloroanilino)‐5‐methyl‐ s ‐triazolo[1,5‐α ]pyrimidine ( 14 ) (98%), which was condensed with various amines to yield the desired 2‐(3,4‐diehloroanilino)‐7‐¶[(dialkylamino)alkyl]arnino¶‐5‐methyl‐ s ‐triazolo[ 1,5‐α]pyrimidines ( 6 a‐d). The structures of the s ‐triazolo[ 1,5‐α ]pyrimidines were based on nmr spectroscopy and ring stability considerations. Several of the amino‐ s ‐triazolo[ 1,5‐α ]pyrimidines possessed antimalarial activity against P. berghei in mice.

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