Synthesis and Characterization of 1,3,4-Oxadiazoles Derived From 9-Fluorenone
In the present work, 9-fluorenone-2-carboxylic acid methyl ester (1) was prepared from 9-fluorenone-2-carboxylic acid and then converted into the acid hydrazide (2). Compound (2), is the key intermediate for the synthesis of several series of new compounds such as substituted 1,3,4-oxadiazole deriva...
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University of Baghdad, College of Science for Women
2013-06-01
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| Series: | مجلة بغداد للعلوم |
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| Online Access: | http://bsj.uobaghdad.edu.iq/index.php/BSJ/article/view/1468 |
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| description | In the present work, 9-fluorenone-2-carboxylic acid methyl ester (1) was prepared from 9-fluorenone-2-carboxylic acid and then converted into the acid hydrazide (2). Compound (2), is the key intermediate for the synthesis of several series of new compounds such as substituted 1,3,4-oxadiazole derivatives (3-6) were synthesized from the condensation of different substituted benzoic acids with compound (2) using POCl3 as condensing agent. Treatment of compound (2) with formic acid gave the N-formyl hydrazide (7), which upon refluxing with phosphorous pentoxide in benzene yielded the corresponding 5-(9-fluorenone-2-yl)-1,3,4-oxadiazole (8). Reaction of hydrazide (2) with phenyl isocyanate to give N-phenyl semicarbazide derivative (9), then this compound (9) convert to 5-(9-fluorenone-2-yl)-N-phenyl-1,3,4-oxadiazole-2-amine (10) via intramolecular cyclization by syrup H3PO4. Also the hydrazide (2) was treated with CS2/KOH afforded 5-(9-fluorenone-2-yl)-1,3,4-oxadiazole-2-thiol (11). Compound (11) was used to react with various alkyl halides and secondary amines to give 5-(9-fluorenone-2-yl)-1,3,4-oxadiazole-2-alkyl thiol (12-15) and 5-(9-fluorenone-2-yl)-1,3,4-oxadiazole-2-N-alkyl (16-19) derivatives respectively. |
| format | Article |
| id | doaj-art-93edb2efaa124a7c9099168529b5c38a |
| institution | Kabale University |
| issn | 2078-8665 2411-7986 |
| language | English |
| publishDate | 2013-06-01 |
| publisher | University of Baghdad, College of Science for Women |
| record_format | Article |
| series | مجلة بغداد للعلوم |
| spelling | doaj-art-93edb2efaa124a7c9099168529b5c38a2025-08-20T03:57:08ZengUniversity of Baghdad, College of Science for Womenمجلة بغداد للعلوم2078-86652411-79862013-06-0110210.21123/bsj.10.2.449-461Synthesis and Characterization of 1,3,4-Oxadiazoles Derived From 9-FluorenoneBaghdad Science JournalIn the present work, 9-fluorenone-2-carboxylic acid methyl ester (1) was prepared from 9-fluorenone-2-carboxylic acid and then converted into the acid hydrazide (2). Compound (2), is the key intermediate for the synthesis of several series of new compounds such as substituted 1,3,4-oxadiazole derivatives (3-6) were synthesized from the condensation of different substituted benzoic acids with compound (2) using POCl3 as condensing agent. Treatment of compound (2) with formic acid gave the N-formyl hydrazide (7), which upon refluxing with phosphorous pentoxide in benzene yielded the corresponding 5-(9-fluorenone-2-yl)-1,3,4-oxadiazole (8). Reaction of hydrazide (2) with phenyl isocyanate to give N-phenyl semicarbazide derivative (9), then this compound (9) convert to 5-(9-fluorenone-2-yl)-N-phenyl-1,3,4-oxadiazole-2-amine (10) via intramolecular cyclization by syrup H3PO4. Also the hydrazide (2) was treated with CS2/KOH afforded 5-(9-fluorenone-2-yl)-1,3,4-oxadiazole-2-thiol (11). Compound (11) was used to react with various alkyl halides and secondary amines to give 5-(9-fluorenone-2-yl)-1,3,4-oxadiazole-2-alkyl thiol (12-15) and 5-(9-fluorenone-2-yl)-1,3,4-oxadiazole-2-N-alkyl (16-19) derivatives respectively.http://bsj.uobaghdad.edu.iq/index.php/BSJ/article/view/14689-Fluorenone, Acid hydrazide derivatives, 1,3,4-Oxadiazole |
| spellingShingle | Baghdad Science Journal Synthesis and Characterization of 1,3,4-Oxadiazoles Derived From 9-Fluorenone مجلة بغداد للعلوم 9-Fluorenone, Acid hydrazide derivatives, 1,3,4-Oxadiazole |
| title | Synthesis and Characterization of 1,3,4-Oxadiazoles Derived From 9-Fluorenone |
| title_full | Synthesis and Characterization of 1,3,4-Oxadiazoles Derived From 9-Fluorenone |
| title_fullStr | Synthesis and Characterization of 1,3,4-Oxadiazoles Derived From 9-Fluorenone |
| title_full_unstemmed | Synthesis and Characterization of 1,3,4-Oxadiazoles Derived From 9-Fluorenone |
| title_short | Synthesis and Characterization of 1,3,4-Oxadiazoles Derived From 9-Fluorenone |
| title_sort | synthesis and characterization of 1 3 4 oxadiazoles derived from 9 fluorenone |
| topic | 9-Fluorenone, Acid hydrazide derivatives, 1,3,4-Oxadiazole |
| url | http://bsj.uobaghdad.edu.iq/index.php/BSJ/article/view/1468 |
| work_keys_str_mv | AT baghdadsciencejournal synthesisandcharacterizationof134oxadiazolesderivedfrom9fluorenone |