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Pyrano-Pyrimidine-4,6-5H-Dione Derivatives Catalyzed by Reusable Silica-Bonded N-Propyl Diethylenetriamine Sulfamic Acid

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Pyrano-Pyrimidine-4,6-5H-Dione Derivatives Catalyzed by Reusable Silica-Bonded N-Propyl Diethylenetriamine Sulfamic Acid Journal of the Association of Arab Universities for Basic and Applied Sciences (JAAUBAS) http://www.ees.elsevier.com/jaaubas Aims: The aim of the Journal is to publish scientific research contributions for the development of our societies, exchange experience and findings among scientists and researchers. This aim will surely lead to the development of the colleges of sciences in the Arab Universities. The Journal of the Association of Arab Universities for Basic and Applied Sciences is aimed to be the main communication between the researchers at the Arab Universities and other overseas counterpart colleges. It will assist the academic staff from local and foreign universities and institutions on publishing research results and studies in the basic and applied sciences. This also will make a bridge between the industry, society and the universities. Scientific research will lead universities to provide distinctive higher education that meets the demands of the Arab countries and qualify their forthcoming generation with high class knowledge and science. Scope: To publish original research and reviews in the field of basic and applied sciences including; Biology, Chemistry, Physics, Mathematics, Operation Research, Statistics, Astronomy, Geology and Engineering. EDITORIAL BOARD Members of the AAU Colleges of Science Society Editor-In-Chief (EIC) Jazan University, Saudi Lebanese Univ., Lebanon Dr. Hashim A. Al-Sayed, General Secretary of Society of Colleges of Science in Arab Universities, Dean of College of Science, University Arabia Islamic University of Lebanon, of Bahrain. P.O. Box 32038, Kingdom of Bahrain. Princess Nourah bint Lebanon [email protected] Abdulrahman Univ., Saudi Holy Spirit University of Managing Editor (ME) Arabia Kaslik, Lebanon Prof. Waheeb E. Alnaser, Vice President for academic and postgraduate programs, University of Bahrain. P.O. Box 32038, Kuwait University, Kuwait Notre Dame Univ., Lebanon Kingdom of Bahrain. [email protected] Sultan Qaboos Univ., Oman University of Baghdad, Iraq [email protected] Qatar University, Qatar University of Mosul, Iraq Editorial Secretary (ES) Dr. Mohammad El-Hilo, Head of Physics Department, University of University of Sharjah, UAE University of Basrah, Iqaq Bahrain, P.O. Box 32038, Kingdom of Bahrain. University of Jordan, Jordan University of Babylon, Iraq [email protected] The Hashemite Univ., Jordan Al-Nahrain University, Iraq Prof. Shoukry. S. Hassan, Dept. of Mathematics, Univ. of Bahrain, Kingdom of Bahrain. Tafila Technical Univ., Jordan University of Anbar, Iraq Dr. Ahmad Taha,, Dept. of Chemistry, Univ. of Bahrain, Kingdom of Jordan University of Science University of Misan, Iraq Bahrain. and Technology, Jordan University of Thi-Qar, Iraq Dr. Mohamed Bououdina,, Dept. of Physics, Univ. of Bahrain, Kingdom of Bahrain. Yarmouk University, Jordan Al Azhar University, Egypt Philadelphia University, Mansoura University, Egypt International Advisory Editorial Board Members Prof. Farouk El-Baz (Geology), Centre for Remote Sensing, Boston Jordan Assiut University, Egypt Univ., USA. Al-Hussain Bin Talal Univ. of Khartoum, Sudan Prof. Mustafa Amr El-Sayed (Chemistry), Georgia Institute of University, Jordan Sudan University of Science Technology, USA. Al Albayt University, Jordan and Technology, Sudan Prof. Mourad E.H. Ismail (Mathematics), Univ. of Central Florida, USA. An-Najah National Univeristy, Al-Neelain Univ., Sudan Prof. Ahmed Sameh (Computer Science), Minnesota Univ., USA. Palestine Omdurman Univ., Sudan Prof. Munir H. Nayfeh (Physics), Illinois University, USA Birzeit University, Palestine University of Tripoli, Libya Prof. Sultan Abu Orabi (Chemistry), Secretary General of AAU, Jubeyha, Amman, Jordan Al-Aqsa University, Palestine Omar Al-Mukhtar Univ., Libya Prof. Riyad Y. Hamzah (Biochemistry), President of Univ. of Bahrain Islamic Univ.-Gaza, Palestine Distinguished Advisory Member Al Azhar Univ.-Gaza, Prof. Ahmed H. Zewail (Nobel laureate), California Institute of Palestine Technology, USA Al-Aqsa University, Palestine Ethics statements and Copyright Correspondence The author(s) are entirely responsible for accuracy of all statements and data Editor- in-Chief, Journal of the Association of Arab contained in the manuscript, as well as accuracy of all references, and for Universities for Basic and Applied Sciences, College of Science, obtaining and submitting written permission from the author and/or publisher University of Bahrain, P.O. Box 32038, of any previously published manuscript used in the submitted manuscript. Sakhir, Kingdom of Bahrain. Copyrights of the published paper will be transferred to the JAAUBAS upon Tel.: (00973) 17437556 / 17437436/ 17437555 notification of acceptance. Fax: (00973) 17449662 Reprints All rights are reserved: Bahrain Publishing Permission: MAAU 394 A soft electronic copy (PDF file) of the published paper will be sent to the ISSN 1815-3852 corresponding author via e-mail Imprint: University of Bahrain Journal of the Association of Arab Universities for Basic and Applied Sciences (2016) 21,1–9 University of Bahrain Journal of the Association of Arab Universities for Basic and Applied Sciences www.elsevier.com/locate/jaaubas www.sciencedirect.com ORIGINAL ARTICLE Facile synthesis and antimicrobial activity of a novel series of 7,8-dihydro-2-(2-oxo-2H- chromen-3-yl)-5-aryl-cyclopenta[b] pyrano-pyrimidine-4,6-5H-dione derivatives catalyzed by reusable silica-bonded N-propyl diethylenetriamine sulfamic acid Prasanna Nithiya Sudhan, Syed Sheik Mansoor * Research Department of Chemistry, Bioactive Organic Molecule Synthetic Unit, C. Abdul Hakeem College, Melvisharam 632 509, Tamil Nadu, India Received 5 June 2014; revised 28 November 2014; accepted 22 December 2014 Available online 21 February 2015 KEYWORDS Abstract An efficient method for the synthesis of a novel series of cyclopenta[b]pyrano Cyclopenta[b]pyrano pyrimidinone derivatives with silica-bonded N-propyl diethylenetriamine sulfamic acid (SBPDSA) pyrimidinones; as catalyst has been achieved by the condensation of 2-amino-4-phenyl-5-oxo-4,5,6,7-tetrahydrocy- Silica-bonded N-propyl clopenta[b]pyran-3-carbonitrile derivatives and coumarin-3-carboxylic acid under solvent free con- diethylenetriamine sulfamic ditions. Antimicrobial studies showed all the target compounds processing good antibacterial and acid; antifungal activities. Coumarin-3-carboxylic acid; ª 2014 University of Bahrain. Publishing services by Elsevier B.V. This is an open access article under the Antimicrobial activity CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/). 1. Introduction pharmacological properties such as anti-inflammatory (Witaicenis et al., 2014), antitumor (Avin et al., 2014), anticancer Coumarins (2-oxo-2H-chromenes) are an old class of com- (Jashari et al., 2014; Zhang et al., 2014), acetylcholinesterase pounds, also known as benzopyranes, comprising a large class (AChE) and butyrylcholinesterase (BuChE) inhibitors of cinnamic acid-derived phenolic compounds found in fungi, (Asadipour et al., 2013), anti-proliferative (Zhao et al., 2014), bacteria and plants, particularly in edible plants from different antibacterial, antifungal and antioxidant (Renuka and Kumar, botanical families. Coumarins and their derivatives have attract- 2013), anti-osteoporotic (Sashidhara et al., 2013) and anti-tuber- ed intense interest in recent years because of their diverse culosis activities (Kawate et al., 2013). A considerable effort has been made for the synthesis of heterocyclic compounds containing coumarin moiety due to * Corresponding author. their wide pharmaceutical importance (Banothu and E-mail address: [email protected] (S. Sheik Mansoor). Bavanthula, 2012; Ghosh and Das, 2012; Augustine et al., Peer review under responsibility of University of Bahrain. http://dx.doi.org/10.1016/j.jaubas.2014.12.001 1815-3852 ª 2014 University of Bahrain. Publishing services by Elsevier B.V. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/). 2 P.N. Sudhan, S. Sheik Mansoor 2012; Khoobi et al., 2011; Khan et al., 2011, 2012; Khurana obtained as a white powder. The content of S obtained from and Kumar, 2009). However, these procedures are not entirely elemental analysis showed that typically a loading of satisfactory and suffer from long reaction time or tedious work 0.99 mmol/g H+ was obtained (Rahi et al., 2012). up. Hence, a method using a nonmetallic catalyst is desirable. Therefore, the introduction of new and efficient methods for 2.3. General procedure to synthesis of 2-amino-4-phenyl-5-oxo- this reaction is still necessary. Toward this goal, we were 4,5,6,7-tetrahydrocyclopenta[b] pyran-3-carbonitrile derivatives prompted to explore new methods for the synthesis of hetero- using Alum (KAl(SO4)2.12H2O) (10 mol%) as catalyst cyclic compounds containing coumarin moiety. Silica-bonded N-propyl diethylenetriamine sulfamic acid has A mixture of aldehydes 1 (1 mmol), malononitrile 2 been reported as a novel catalyst for chemoselective synthesis of (1 mmol), cyclopentane-1,3-dione 3 (1 mmol), and powdered 1,1-diacetates (Sefat et al., 2011), and synthesis of a-aminoni- Alum (KAl(SO4)2Æ12H2O) (10 mol%), under solvent-free triles (Rahi et al., 2012). However, to the best of our knowledge, conditions was stirred at 70 °C for appropriate time there are no examples on the use of SBPDSA as catalyst for the (Scheme 1). The progress of the reaction was monitored synthesis of 7,8-dihydro-2-(2-oxo-2H-chromen-3-yl)-5-aryl-cy-
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