Environmentally Benign Synthesis of 2-Pyrazolines and Cyclohexenones Incorporating Naphthalene Moiety and Their Antimicrobial Evaluation

doi:10.1007/s40242-013-3290-5

高等学校化学研究 ›› 2014, Vol. 30 ›› Issue (1): 68-74.doi: 10.1007/s40242-013-3290-5

Environmentally Benign Synthesis of 2-Pyrazolines and Cyclohexenones Incorporating Naphthalene Moiety and Their Antimicrobial Evaluation

Al-Bogami Abdullah Saad

Department of Chemistry, Faculty of Science, King Abdulaziz University, North Jeddah, Jeddah 21589, Saudi Arabia

收稿日期:2013-07-10 修回日期:2013-09-13 出版日期:2014-02-01 发布日期:2013-10-11
通讯作者: Al-Bogami Abdullah Saad,E-mail:chem_org@hotmail.com E-mail:chem_org@hotmail.com
基金资助:
Supported by the Project of the Green Chemistry Research Laboratory, Faculty of Science, King Abdulaziz Univeristy, North Jeddah, Saudi Arabia.

Environmentally Benign Synthesis of 2-Pyrazolines and Cyclohexenones Incorporating Naphthalene Moiety and Their Antimicrobial Evaluation

Al-Bogami Abdullah Saad

Department of Chemistry, Faculty of Science, King Abdulaziz University, North Jeddah, Jeddah 21589, Saudi Arabia

Received:2013-07-10 Revised:2013-09-13 Online:2014-02-01 Published:2013-10-11
Contact: Al-Bogami Abdullah Saad,E-mail:chem_org@hotmail.com E-mail:chem_org@hotmail.com
Supported by:
Supported by the Project of the Green Chemistry Research Laboratory, Faculty of Science, King Abdulaziz Univeristy, North Jeddah, Saudi Arabia.

摘要/Abstract

摘要：

We reported the environmental benign synthesis of chalcones, 2-pyrazolines and cyclohexanones under microwave irradiation. Chalcones were obtained by the condensation of each of 2-hydroxyacetophenone derivatives with α-naphthaldehyde under microwave irradiation. The condensation reactions of each of synthesized chalcones with phenyl hydrazine under microwave irradiation in the presence of dry acetic acid as a cyclizing agent gave 2-pyrazolines. Also, the new cyclohexenone derivatives, valuable intermediates to synthesize fused heterocycles, have been prepared by the cyclocondensation of each of hydroxychalcones with ethyl acetoacetate. The structures of the synthesized compounds were elucidated by infrared(IR) spectrometry, nuclear magnetic resonance(NMR), mass spectrometry(MS) and elmental analysis. The results indicate that unlike classical heating, microwave irradiation results in higher yields with shorter and cleaner reactions. The synthesized compounds were screened for antimicrobial activity against Staphylococcus aureus, Escherichia coli, Candida Albicans and Aspergillus niger. We clarified the effects of different substituents in the tested compounds on the obtaind antibacterial activities and antifungal activities .

关键词: Microwave irradiation, 2-Hydroxyacetophenone, α-Naphthaldehyde, Pyrazoline, Cyclohexenone, Anti-microbial activity

Abstract:

Key words: Microwave irradiation, 2-Hydroxyacetophenone, α-Naphthaldehyde, Pyrazoline, Cyclohexenone, Anti-microbial activity

Al-Bogami Abdullah Saad. Environmentally Benign Synthesis of 2-Pyrazolines and Cyclohexenones Incorporating Naphthalene Moiety and Their Antimicrobial Evaluation[J]. 高等学校化学研究, 2014, 30(1): 68-74.

Al-Bogami Abdullah Saad. Environmentally Benign Synthesis of 2-Pyrazolines and Cyclohexenones Incorporating Naphthalene Moiety and Their Antimicrobial Evaluation[J]. Chemical Research in Chinese Universities, 2014, 30(1): 68-74.

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Environmentally Benign Synthesis of 2-Pyrazolines and Cyclohexenones Incorporating Naphthalene Moiety and Their Antimicrobial Evaluation

Environmentally Benign Synthesis of 2-Pyrazolines and Cyclohexenones Incorporating Naphthalene Moiety and Their Antimicrobial Evaluation

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