Abstract
2-(α-Phenylacetyl) benzohydrazide (1) was prepared through the reaction of (Z)-3-benzylidene phthalide and hydrazine hydrate. Treatment of compound (1) with substituted benzoyl chloride yielded N'-aroyl-2-(α-phenyl acetyl) benzohydrazide (2a-e) which upon reaction with ammonium acetate provided the corresponding 2-phenyl-1-(2-(5-aryl-1,2,4-triazole-3-yl)phenyl)ethanones (3a-e). While the reaction of compound (1) with substituted benzaldehyde gave the hydrazones represented by N'-arylidene-2-(α-phenylacetyl) benzohydrazide derivatives (4a-f). Intramolecule cyclization of the latter compounds by means of acetic anhydride yielded 2-(α-phenylacetyl)phenyl-4-acetyl-4,5-dihydro-5-aryl-1,3,4-oxadiazoles (5a-f). Compounds 2-(α-phenylacetyl)-N-(3,6-diphenyl-5-aryl-5,6-dihydro-1,2,4-triazine-4yl) benzamide (6a-f) were also obtained from the direct Diel-Alder reaction between dibenzylidine hydrazine as diene and compounds (4a-f) as dienophile enhanced by microwave irradiation. The assigned structure of the prepared compounds were corroborated by available physical and spectral methods
Highlights
Among many class of small molecule libraries, 3-benzylidene(alkylidene) phthalides are very attractive template for combinatorial synthesis, due to the large number of substitution pattrens (Dalloul, 2010; Viña et al, 2009; del Olmo et al, 2006; Rios and Delgado, 1999; Hrnčiar et al, 1994; Humber, 1974; Rosenthal and Yalpani, 1965; Litvan and Stoll, 1958) and it have a great deals of attention because of it’s wide applications in idusterial (Shibata and Gaesser, 1991; Scholl et al, 1989; Conner, 1982) and biological fields (Kurume et al, 2008; Kanazawa and Terada, 2007; Kundu et al, 1998; Ganji et al, 1993; Ibrahim, 1991)
In this presentation 3-benzylidene phthalide was used as active synthon to obtain different heterocyclic compounds represented by 1,2,4-triazoles that have many biological, pharmaceutical and agricultural applications (Khanage et al, 2010; Singh, 2009; Taha and AlBadry, 2006; Hsu et al, 2005; Sasaki et al.,1984; Katratizky and Rees, 1984), 1,3,4oxadiazoles which present in compounds have higher biological, pharmaceutical and agricultural activities (Swamy et al, 2010; mulwad and Chashar,2006; Khare et al, 2005; Mishra and Singh, 2000; Katratizky and Rees, 1984), and 1,2,4-triazines that have reported to exhibit various pharmaceutical properties and wide applications in agricultural and idusterial fields (Dalloul and Al-Shorafa, 2009; Kamble and Sudha, 2006; Nasr, 2005)
Prompted by these observations and starting from (Z)-3-benzylidene phthalide, the series of new 1,2,4-trazoles (3a-e), and 1,3,4-oxadiazoles (5a-f) were commonly performed under usual mild and thermal methods, while a simple and efficient one-pot procedure was followed for generation of 1,2,4-triazines (6a-f) with microwave assistance
Summary
Email : khazaalyounis @ yahoo . com (Received 20/ 9 / 2010 ; Accepted 25 / 4 / 2011 ). While the reaction of compound (1) with substituted benzaldehyde gave the hydrazones represented by N'-arylidene-2-(α-phenylacetyl) benzohydrazide derivatives (4a-f). Intramolecule cyclization of the latter compounds by means of acetic anhydride yielded 2-(α-phenylacetyl)phenyl-4-acetyl-4,5-dihydro-5-aryl-1,3,4oxadiazoles (5a-f). الملخص -3-(( من خلال تفاعل )سس1)اسيتيل فنيل( بنزوهيدرازيد-α)-2 في هذا البحث تم تحضير المركب ( مع معوضات كلوريد البنزويل وأعطى1) عند معاملة المركب.بنزايليدين فثالايد مع الهيدرازين المائي ( والتي عند تفاعلها مع خلات الامونيوم اعطت2a-e) اسيتيل فنيل( بنزوهيدرازيد-α) -2- ارويل-N' معوضات. بينما ادى تفاعل.( المقابلة3a-e) يل( فنيل( ايثانون-3-ترايازول-4،2،1-اريل-5)-2)-1- فنيل-2 مشتقات اسيتيل-α)-2-ارايليدين-N' ( مع معوضات البنزالديهايد إلى تكوين الهيدرازونات المتمثلة بالمركبات1) المركب ( في تفاعلات الغلق الضمني بوجود انهدريد الخليك لتعطي4a-f) أدخلت المركبات.(4a-f) الفنيل( بنزوهيدرازيد .(5a-f) اوكسادايازول-4،3،1-اريل-5-ثنائي هيدرو-4،5- اسيتيل-4-اسيتيل فنيل( فنيل-α)-2 معوضات (يل-4- ترايازين-4,2,1- ثنائي هيدرو-5,6-اريل-5-ثنائي فنيل-6,3)-N–(اسيتيل فنيل-α)-2 أما المركبات ( كداينوفيل وثنائي4a-f) الدر المباشر بين المركبات-( فقد تم تحضيرها من خلال تفاعل ديلز6a-f) بنزاميد شخصت جميع المركبات المحضرة.بنزايليدين هيدرازين كدايين والمحفز باستخدام التشعيع بالموجات الدقيقة. اسيتيل فنيل( بنزوهيدرازايد-α)-2 ، بنزايليدين فثاليد-3-( )سس:الكلمات المفتاحية
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