synthesis and analgesic activity of some new pyrazoles and triazoles bearing a 6,8-dibromo-2-methylquinazoline moiety氮杂四唑合成和镇痛活性的一些新的摘要和轴承6 8-dibromo-2-methylquinazoline一半.pdfVIP

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synthesis and analgesic activity of some new pyrazoles and triazoles bearing a 6,8-dibromo-2-methylquinazoline moiety氮杂四唑合成和镇痛活性的一些新的摘要和轴承6 8-dibromo-2-methylquinazoline一半.pdf

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synthesis and analgesic activity of some new pyrazoles and triazoles bearing a 6,8-dibromo-2-methylquinazoline moiety氮杂四唑合成和镇痛活性的一些新的摘要和轴承6 8-dibromo-2-methylquinazoline一半

Molecules 2011, 16, 10187-10201; doi:10.3390/molecules161210187 OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis and Analgesic Activity of Some New Pyrazoles and Triazoles Bearing a 6,8-Dibromo-2-methylquinazoline Moiety Hosam A. Saad 1,3,*, Nermen A. Osman 2 and Ahmed H. Moustafa 3 1 Department of Chemistry, Faculty of Science, Taif University, Taif 21974, Saudi Arabia 2 Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig 44511, Egypt; E-Mail: naosman2007 @ 3 Department of Chemistry, Faculty of Science, Zagazig University, Zagazig 44511, Egypt; E-Mail: ah_hu_mostafa@ * Author to whom correspondence should be addressed; E-Mail: h_saadzag@; Tel.: +20-100-537-3242; Fax: +20-55-228-5374. Received: 10 October 2011; in revised form: 1 December 2011 / Accepted: 2 December 2011 / Published: 7 December 2011 Abstract: 2-(6,8-Dibromo-2-methylquinazolin-4-yloxy)-acetohydrazide (4) was prepared by the reaction of 6,8-dibromo-2-methylbenzo-[d][1,3]oxazin-4-one with formamide to afford quinazolinone 2, followed by alkylation with ethyl chloroacetate to give the ester 3. Treatment of ester 3 with hydrazine hydrate and benzaldehyde afforded 4 and styryl quinazoline 5. The hydrazide was reacted with triethyl orthoformate, acetylacetone and ethyl acetoacetate and benzaldehyde derivatives to afford the corresponding pyrazoles 6, 7, 9 and hydrazone derivatives 10a-c. Cyclization of hydrazones 10a-c with thiog