Abstract
A comprehensive and facile method for the synthesis of new functionalized bis-heterocyclic compounds containing a thieno[2,3-b]thiophene motif is described. The hitherto unknown bis-pyrazolothieno[2,3-b]thiophene derivatives 2a–c, bis-pyridazin othieno[2,3-b]thiophene derivatives 4, bis-pyridinothieno[2,3-b]thiophene derivatives 6a,b, and to an analogous bis-pyridinothieno[2,3-b]thiophene nitrile derivatives 7 are obtained. Additionally, the novel bis-pyradazinonothieno[2,3-b]thiophene derivatives 9, and nicotinic acid derivatives 10, 11 are obtained via bis-dienamide 8. The structures of all newly synthesized compounds have been elucidated by 1H, 13C NMR, GCMS, and IR spectrometry. These compounds represent a new class of sulfur and Nitrogen containing heterocycles that should also be of interest as new materials.
Highlights
Heterocycles are well known for displaying a wide range of biological properties [1]
Keeping the above facts in mind and in continuation of our interest in the synthesis of bis(hetrocycles) [28,29,30,31], we describe a simple and efficient route for the synthesis of novel bis(enaminones) and studied their synthetic utilities as key intermediates for the synthesis of novel bis-heterocycles pyrazoles, pryridines, and pyridazine derivatives
Enaminones 1 were prepared by different synthetic approaches and their use as building blocks for the synthesis of a wide variety of heterocycles has been investigated [3,32,33,34,35]
Summary
Heterocycles are well known for displaying a wide range of biological properties [1]. The structural diversity and biological importance of N-containing heterocycles have made them attractive synthetic targets over many years. Compounds with pyrazole ring are of interest due to their broad spectrum of biological activities as NOS inhibitors [4], monoamine oxidase inhibitor [5], Int. J. A number of pyridine and pyridazine derivatives are gaining synthetic interest in recent years due to their broad spectrum of biological activities [11]. Keeping the above facts in mind and in continuation of our interest in the synthesis of bis(hetrocycles) [28,29,30,31], we describe a simple and efficient route for the synthesis of novel bis(enaminones) and studied their synthetic utilities as key intermediates for the synthesis of novel bis-heterocycles pyrazoles, pryridines, and pyridazine derivatives
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