Heterocyclization of 2-thiophenamine: Design of novel thiophene with azole and azine moieties

Hamed, Eman O.; Assy, Mohamed G.; El-Said, Eman; Shehta, Wael

doi:10.21608/bfszu.2022.130929.1123

	Heterocyclization of 2-thiophenamine: Design of novel thiophene with azole and azine moieties
Bulletin of Faculty of Science, Zagazig University
Article 5, Volume 2022, Issue 2, July 2022, Page 47-56 PDF (1.12 MB)
Document Type: Original Article
DOI: 10.21608/bfszu.2022.130929.1123
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Authors
Eman O. Hamed¹; Mohamed G. Assy²; Eman El-Said ²; Wael Shehta²
¹Department of chemistry, Faculty of Science, Zagazig University, Zagazig44519, Egypt
²Department of chemistry, Faculty of Science, Zagazig University, Zagazig, 44519, Egypt
Abstract
Thiophenamine of type 1 undergo several functionalization and heterocyclization, thus reaction of target 1 with diethyl succinate furnished benzothiophene derivative 4 through condensation followed by intramolecular cyclocondensation and subsequent evolution of 3 H2. Keeping diethyl malonate and amino derivative 1 provide hydroxypyridine derivative 7, may be via 3 °r amine 5 that added the active methylene to the ester group followed by hydrolysis and subsequent decarboxylation. Also, Target 1 undergo cyclocondensation with ethyl acetoacetate to produce acetyl pyridine of type 10. Alkylation of 1 with N-phenyl chloroacetamide provided alkylation derivative 11. Acylation of compound 1 with chloroacetyl chloride followed by cyclization leads to chloropyrrole derivative 14. Compound 14 reacted with NH4SCN to give non isolable pyrrole 15 followed by enolization and subsequent intramolecular cycloaddition providing fused pyrrole 16. Compound 1 reacted with succinic anhydride and ethyl cyanoacetate to provide acylated derivative 17 and aminocyanopyridine 19, respectively. Compound 19 undergo azidolysis and acetylation producing pyridine derivatives 20 and 21, respectively. Compound 19 added its amino group to heteroallene electrophilic carbon of benzoyl isothiocyanate followed by intramolecular heterocyclization producing pyridopyrimidine derivative 23.
Keywords
Thiophene amine; Pyridine; Pyrrole; Pyridopyrimidines


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