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Synthesis of New 3-(Pyridin-6-yl)pyrazolo[1,5-a]pyrimidines

โœ Scribed by Nadia Sobhy Ibrahim; Mona Hassan Mohamed; Mohamed Hilmy Elnagdi


Publisher
John Wiley and Sons
Year
1987
Tongue
English
Weight
218 KB
Volume
320
Category
Article
ISSN
0365-6233

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โœฆ Synopsis


Eingegangen am 16. Juli 1986 New 3-(pyridin-6-yl)

pyraolo [ 1,5-u]pyrimidines were synthesized from (pyridin-6-y1)malonodinitrile 58, ethyl (pyridin-6-y1)cyanoacetate 5b and (pyridin-6-y1)benzoylacetonitrile 5c. Compounds 58-c were obtained from the 4,4,4-trichlorobut-2-enenitriles 2 and 1-pheny1ethylidene)malonodinitrile (1).

Syntbese neuer 3-(Pyridia-6-yl)pyrazoldlJ-a~yrirnidine

Neue Titelverbindungen wurden aus dem (Pyridin-6-y1)malonodinitril Sa, dem (Pyridin-6-y1)cyanessigsaureester 5b und dem (Pyridin-6-yl)benzoylacetonitril 5c synthetisiert. Die Verbindungen 58-5c wurden aus den 4,4,4-Trichlorbut-2-ennitrilen 2 und (1-Phenylethy1iden)malonodinitril gewonnen.

Schistosomiasis is considered to be one of the most diffcult diseases to treat'). Accordingly considerable attention has been directed toward the development of usefull chemotherapeutic agents. The observation that certain substituted pyrazolo[ 1,5-a]pyrimidines have considerable antischistosomiasis activity23 3) have prompted us to start a research project aiming to prepare some new pyrazoloI 1,5-alpyrimidines. Although plenty of substituted pyrazolo[ 1,5-alpyrimidines have been prepared4, 9, to our knowledge 3-(pyridin-6-yl)-pyraolo [ 1,5-alpyrimidines have not yet been prepared. As pyrazolo[ 1,5-alpyrimidines are prepared from 5-aminopyrazoles, we searched literature to find their preparation from 6-(5-aminopyrazol-4-yl)pyridines, we realized however that these compounds have not yet been prepared.


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m. p.=248-250GC (dec.; from methanol); [.ID= -129.' (DMSO, c = 1.00); 'H-NMR (D6-DMSO); t=4.13 and 4.18 (s, I-H+l'-H and s, 2 2-benzyl-H, or vice versa); MS: 520 (M+)]. The amino ketone ( 8 ) is probably first formed, being later aromatized by dimerization and air oxidation to yield ( 9 ) . The firs