Abstract
This paper reports details about the synthesis of a series of novel functionalized symmetrical bis-heterocyclic compounds containing a thieno[2,3-b]thiophene motif. Bis-thiazole derivatives 2, 3a-c and thiazolo[3,2-a]pyridine derivatives 4a-c are achieved. The hitherto unknown dihydrothiophene derivatives 6a-d via bis-pyridimium salt 5 are obtained. Additionally, the novel hydrazonothieno[2,3-b]thiophene derivatives 10a-c are obtained via bis-tosylacetylthieno[2,3-b]thiophene derivative 9. All compounds are characterized by 1H-, 13C-NMR, GCMS, IR, and UV-vis spectrometry. These compounds represent a new class of sulfur and nitrogen containing heterocycles that should also be of interest as new materials.
Highlights
Thienothiophene derivatives have been developed for different purposes in the pharmaceutical field and have been tested as potential antitumor, antiviral, antibiotic, and antiglaucoma drugs, or as inhibitors of platelet aggregation [1–5]
Compounds 3a-c were alternatively obtained by the reaction of the treatment of bis-2-bromoacetylthieno[2,3-b]thiophene derivative 1 with
Compounds 4a-c were alternatively obtained by reaction of the treatment of bis-thiazole derivative 2 with 2-cyano-2-arylmethylenethioacetamide derivatives in ethanol/DMF
Summary
Thienothiophene derivatives have been developed for different purposes in the pharmaceutical field and have been tested as potential antitumor, antiviral, antibiotic, and antiglaucoma drugs, or as inhibitors of platelet aggregation [1–5]. On the other hand thiophene derivatives represent a class of important and well-studied heterocycles [13,14]. Thiazoles and their derivatives have attracted continuing interest over the years because of their diverse biological activities [15,16]. They have found application in drug development for the treatment of allergies [15], hypertension, inflammation, schizophrenia, bacterial and HIV infections [17–21]. On the other hand substituted thiazolo pyridines represent an important class of annulated heterocycles with diverse types of pharmaceutical [22] and pesticide activity [23–28]. We have found that the bis-2-bromoacetylthieno[2,3b]thiophene derivative 1, is a versatile, readily accessible building block for the synthesis of several new heterocyclic compounds of biological potency
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