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Synthesis of a new series of pyrazolo[1,5-a]pyrimidines structurally related to zaleplon

✍ Scribed by Pier Giovanni Baraldi; Francesca Fruttarolo; Mojgan Aghazadeh Tabrizi; Romeo Romagnoli; Delia Preti; Ennio Ongini; Hussein El-Kashef; María Dora Carrión; Pier Andrea Borea

Publisher
Journal of Heterocyclic Chemistry
Year
2007
Tongue
English
Weight
371 KB
Volume
44
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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The reaction between 3‐(dimethylamino)/3,3‐bis(methylthio)‐1‐(substituted)prop‐2‐en‐1‐ones and 4‐substituted‐5‐amino‐1__H__‐pyrazoles afforded new pyrazole[1,5‐a]pyrimidines structurally related to Zaleplon. The chemical modifications introduced at the 3‐, 5‐, and 7‐positions of the bicyclic structure revealed new promising candidates for the treatment of sleep disorders.

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Synthesis of new pyrazolo[1,5-a]pyrimidi
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## Abstract While 3(5)‐aminopyrazole reacts with enaminonitrile to yield pyrazolo[1,5‐__a__]pyrimidines, 3‐amino‐5‐pyrazolone reacts with the same reagents to yields pyrazolo[3,4‐__b__]pyridines.

Synthesis of New 3-(Pyridin-6-yl)pyrazol
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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-pheny1et