Synthesis and antibacterial activity of some novel thieno[2,3-c]pyridazines using 3-amino-5-phenyl-2-ethoxycarbonylthieno[2,3-c]pyridazine as a starting material
3-Amino-5-phenyl-2-ethoxycarbonylthieno[2,3-c]pyridazine (6) was prepared by reaction of 4-cyano-6-phenylpyridazine-3(2H)-thione (4) with ethyl chloroacetate in the presence of sodium ethoxide. Hydrazinolysis of compound 6 yielded the corresponding carbohydrazide, (9) which on treatment with acetyla...
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doaj-67eb42d2bc55499dbef0df6acb3513ee2020-11-25T00:49:09ZengElsevierArabian Journal of Chemistry1878-53522014-11-017577578010.1016/j.arabjc.2010.12.020Synthesis and antibacterial activity of some novel thieno[2,3-c]pyridazines using 3-amino-5-phenyl-2-ethoxycarbonylthieno[2,3-c]pyridazine as a starting materialAhmed S.N. Al-Kamali0Ahmed A. Al-Hazmi1Mohammed H.M. Alhousami2Mokhtar A. Al-Masany3Chemistry Department, Faculty of Applied Science, Taiz-University, YemenChemistry Department, Faculty of Science, Ibb University, Ibb 70270, YemenChemistry Department, Faculty of Applied Science, Taiz-University, YemenChemistry Department, Faculty of Applied Science, Taiz-University, Yemen3-Amino-5-phenyl-2-ethoxycarbonylthieno[2,3-c]pyridazine (6) was prepared by reaction of 4-cyano-6-phenylpyridazine-3(2H)-thione (4) with ethyl chloroacetate in the presence of sodium ethoxide. Hydrazinolysis of compound 6 yielded the corresponding carbohydrazide, (9) which on treatment with acetylacetone and ethyl acetoacetate produced the novel thieno[2,3-c]pyridazines (10 and 11). Treatment of compound 9 with nitrous acid yielded the corresponding carboazide (13), which upon boiling in toluene furnished imidazo[4′,5′:4,5]thieno[2,3-c]pyridazine (15). Pyrimidothienopyridazines (16–18) were achieved by cyclocondensation of compound 9 with some reagents, namely acetic anhydride, formic acid, and triethyl orthoformate. The newly synthesized compounds were confirmed by elemental analyses and spectral data. The antibacterial activities of the new compounds were also evaluated.http://www.sciencedirect.com/science/article/pii/S1878535210002844PyridazineThienopyridazinesPyrimidothienopyridazinesAntibacterial activity |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Ahmed S.N. Al-Kamali Ahmed A. Al-Hazmi Mohammed H.M. Alhousami Mokhtar A. Al-Masany |
spellingShingle |
Ahmed S.N. Al-Kamali Ahmed A. Al-Hazmi Mohammed H.M. Alhousami Mokhtar A. Al-Masany Synthesis and antibacterial activity of some novel thieno[2,3-c]pyridazines using 3-amino-5-phenyl-2-ethoxycarbonylthieno[2,3-c]pyridazine as a starting material Arabian Journal of Chemistry Pyridazine Thienopyridazines Pyrimidothienopyridazines Antibacterial activity |
author_facet |
Ahmed S.N. Al-Kamali Ahmed A. Al-Hazmi Mohammed H.M. Alhousami Mokhtar A. Al-Masany |
author_sort |
Ahmed S.N. Al-Kamali |
title |
Synthesis and antibacterial activity of some novel thieno[2,3-c]pyridazines using 3-amino-5-phenyl-2-ethoxycarbonylthieno[2,3-c]pyridazine as a starting material |
title_short |
Synthesis and antibacterial activity of some novel thieno[2,3-c]pyridazines using 3-amino-5-phenyl-2-ethoxycarbonylthieno[2,3-c]pyridazine as a starting material |
title_full |
Synthesis and antibacterial activity of some novel thieno[2,3-c]pyridazines using 3-amino-5-phenyl-2-ethoxycarbonylthieno[2,3-c]pyridazine as a starting material |
title_fullStr |
Synthesis and antibacterial activity of some novel thieno[2,3-c]pyridazines using 3-amino-5-phenyl-2-ethoxycarbonylthieno[2,3-c]pyridazine as a starting material |
title_full_unstemmed |
Synthesis and antibacterial activity of some novel thieno[2,3-c]pyridazines using 3-amino-5-phenyl-2-ethoxycarbonylthieno[2,3-c]pyridazine as a starting material |
title_sort |
synthesis and antibacterial activity of some novel thieno[2,3-c]pyridazines using 3-amino-5-phenyl-2-ethoxycarbonylthieno[2,3-c]pyridazine as a starting material |
publisher |
Elsevier |
series |
Arabian Journal of Chemistry |
issn |
1878-5352 |
publishDate |
2014-11-01 |
description |
3-Amino-5-phenyl-2-ethoxycarbonylthieno[2,3-c]pyridazine (6) was prepared by reaction of 4-cyano-6-phenylpyridazine-3(2H)-thione (4) with ethyl chloroacetate in the presence of sodium ethoxide. Hydrazinolysis of compound 6 yielded the corresponding carbohydrazide, (9) which on treatment with acetylacetone and ethyl acetoacetate produced the novel thieno[2,3-c]pyridazines (10 and 11). Treatment of compound 9 with nitrous acid yielded the corresponding carboazide (13), which upon boiling in toluene furnished imidazo[4′,5′:4,5]thieno[2,3-c]pyridazine (15). Pyrimidothienopyridazines (16–18) were achieved by cyclocondensation of compound 9 with some reagents, namely acetic anhydride, formic acid, and triethyl orthoformate. The newly synthesized compounds were confirmed by elemental analyses and spectral data. The antibacterial activities of the new compounds were also evaluated. |
topic |
Pyridazine Thienopyridazines Pyrimidothienopyridazines Antibacterial activity |
url |
http://www.sciencedirect.com/science/article/pii/S1878535210002844 |
work_keys_str_mv |
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