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Synthesis of Bis-heterocyclic phenyl containing -4 – oxo – 1,3 – thiazolidine, 2,3 – dihydrothiazole, 1, 2,4 – triazolo [3, 4b ] – 1,3,4 – thiadiazine and pyrazol derivatives | ||
| Journal of Al-Nahrain University - Science | ||
| Article 1, Volume 14, Issue 2, 2011, Pages 67-74 | ||
| Author | ||
| Yasmeen A. Al-Daeif | ||
| Abstract | ||
| Abstract This research describes the synthesis of some new different substituted bicyclic phenyl derivatives. To obtain the target compounds, the reaction steps shown in scheme (I) and (II) were of a feasible strategy. The synthon terphthalic acid hydrazide [2] which was prepared from methyl terphthalate [1] with hydrazine hydrate, was used for the preparation of six types of new heterocyclic derivatives. Acid hydrazide [2] reacts with carbon disulfide in the presence of potassium hydroxide and p–hydroxy benzaldehyde to give the corresponding potassium carbodithioate salt [3] and shiff’s base [5] derivatives respectively. Treatment of the latter salt with p- bromophenacyl bromide afforded thiazolidine -2- thione[4], cyclization of shiff’s base [5] using mercapto acetic acid resulted in the formation of -4- oxo-1,3 - thiazolidne [6]. 1,2,4 – triazolo [3, 4b] - 1,3,4 – thiadiazine [9] was synthesized from basic cyclization of the intermediate product [8] which was obtained from the reaction between 2 – mercapto – 1,3,4 – oxadiazole [7] and p-bromo phenacyl bromide. Furthermore, the hydrazino – 1,3,4 – oxadiazole [10], which was obtained from the reaction between of compound [7] with hydrazine hydrate, was then reacted with CS2 / pyridine and acetyl aceton to give the corresponding 1,3,4 – triazolo [5,1b] oxadiazole [11] and pyrazole [12] derivatives respectively, scheme (II). All synthesized compounds structures were characterized by measurements some of its physical proprieties and some specific reactions and spectral methods FTIR, 1H NMR for compound [6] and [8]. | ||
| Keywords | ||
| oxadiazole; thiazolidine; fused heterocyclic ring; pyrazol | ||
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