Abstract
Condensation of sodium 3-oxo-3-(1-phenyl-1
H
-pyrazol-4-yl)prop-1-en-1-olate (
2
) with several heterocyclic amines, cyanoacetamide, cyanothioacetamide, and 2-cyanoacetohydrazide gives pyrazolo[1,5-
a
]pyrimidines (
5a–d
), pyrido[2′,3′:3,4]pyrazolo[1,5-
a
]pyrimidine (
9
), benzo[4,5]imidazo[1,2-
a
]pyrimidine (
10
), [1,2,4]triazolo[1,5-
a
]pyrimidine (
11
), and pyridine derivatives (
12–14
). Also, thieno[2,3-
b
]pyridines (
15–18
) were synthesized via pyridinethione (
13
) with
α
-halo ketones and
α
-halo ester. Structures of the newly synthesized compounds were elucidated by elemental analysis, spectral data, alternative synthetic routes, and chemical transformation whenever possible.