Abstract
Thienopyrazole 2, 3, 5, or 6 and thienopyrazolothiazepine 7, 9, and 11 derivatives were prepared via the reaction of the 3โaminopyrazolineโ5โone 1 with CS~2~ and different molar ratio of a variety of halo compounds having an active methylene under PTC conditions. Also, treatment of 1 with CS~2~ and alcoholic KOH in 2:1:1 molar ratio afforded dipyrazolopyridine derivatives 12 and 14. On other hand, the pyrazolothiadiazineone derivative 13 was obtained by treating compound 1 with CS~2~ and alcoholic KOH in 1:2:2 molar ratio. Under PTC conditions, compound 1, CS~2~, and ethyl cyanoacetate or malononitrile to gave the pyrazolopyridine derivatives 16 and 17. Coupling of compound 1 with diazonium acetates afforded the hydrazone derivatives 18a,b, which were oxidized with bromine to give pyrazolotriazoles 19a,b or cyclized with aldehydes to give pyrazolotriazine derivatives 20aโe. Bromination of compound 1 afforded monobromopyrazole derivative 21, which could be condensed to a dipyrazolopyrazindione 23. Finally, the dibromopyrazole derivative 22 was cyclized with 2โmercaptoethanol or oโphenylenediamine to give the spiropyrazoles 24a,b. ยฉ 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:211โ217, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10129