Chemistry of C-Heteroarylhydrazidoyl Halides. Synthesis and Reactions of N-(p-Nitrophenyl)-C-(2-thienyl)-formohydrazidoyl Halides

Hassaneen, Hamdi M.; Mousa, H. A. H.; Abed, N. M.; Shawali, Ahmad S.

doi:10.3987/com-87-4381

Cited by 60 publications

(31 citation statements)

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“…N-(4-Nitrophenyl)thiophene-2-carbohydrazonoyl chloride (1) [22] was reacted with ethyl 1,2,3,4-tetrahydro-6-methyl-4-phenyl-2-thioxopyrimidine-5-carboxylate (2) [23] in 1,4-dioxane solution in the presence of triethylamine under reflux to give a single product consistent with Structure 7 based on spectroscopic data (IR, 1 H-NMR, and MS) and elemental analyses (Scheme 1). The mass spectrum of the isolated product 7 showed the molecular ion peak at the expected m/z value.…”

Section: Chemistrymentioning

confidence: 99%

Ethyl 7-Methyl-1-(4-nitrophenyl)-5-phenyl-3-(thiophen-2-yl)-1,5-dihydro-[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylate

Gomha

Muhammad

Edrees

2017

Molbank

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A novel compound, ethyl 7-methyl-1-(4-nitrophenyl)-5-phenyl-3-(thiophen-2-yl)-1,5-dihydro[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylate (7) was synthesized by reaction of N-(4-nitrophenyl)thiophene-2-carbohydrazonoyl chloride (1) with ethyl 6-methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (2). The mechanism of the studied reaction is discussed and the assigned structure was confirmed by elemental analysis and spectral data. Moreover, the in vitro antitumor activities against human lung (A-549) and human hepatocellular carcinoma (HepG-2) cell lines were determined by the MTT method, and the results indicated a high potency compared with the employed standard antitumor drug (Cisplatin).

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Section: Chemistrymentioning

confidence: 99%

Ethyl 7-Methyl-1-(4-nitrophenyl)-5-phenyl-3-(thiophen-2-yl)-1,5-dihydro-[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylate

Gomha

Muhammad

Edrees

2017

Molbank

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“…Elemental analyses of the products were carried out at the Microanalytical Center of Cairo University, Giza, Egypt. Hydrazonoyl halides were prepared following literature procedures [18][19][20][21][22][23][24]. DMF-DMA, dipropylamine and ethyl propiolate were purchased from Merck Company.…”

Section: Instrumentationmentioning

confidence: 99%

Regioselective synthesis of some functionalized 3,4’-bis-(pyrazolyl)ketones and chemoselectivity in their reaction with hydrazine hydrate

Hassaneen

Shawali

2013

Eur. J. Chem.

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“…E. M. A. thanks the Swiss Federal Government for the provision of a National Scholarship for Foreign Students. [39], and 10o [40], and 3,4-dihydroisoquinolines 8 [17] and 12 [41], a-cyanocinnamates 15a ± d [42] and 15e [43], and benzylidenemalononitriles 19a ± d [42], 19f [44], 19h [45], and 19i [46] were prepared according to the procedures reported.…”

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confidence: 99%

New Routes to Fused Isoquinolines

Awad

Elwan

Hassaneen

et al. 2002

HCA

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Treatment of 6,7-diethoxy-3,4-dihydroisoquinoline (8) and its 1-methyl derivative 12 with hydrazonoyl halides 10 in the presence of Et 3 N in THF under reflux afforded the corresponding 5,6-dihydro-1,2,4-triazolo[3,4-a]isoquinolines 11 and 13, respectively, in high yield (Schemes 2 and 3). The products are formed via regioselective 1,3-dipolar cycloaddition of the intermediate nitrilimines 9 with the isoquinoline CN bond. Reaction of 6,7-diethoxy-3,4-dihydroisoquinoline-1-acetonitrile (4a) with ethyl a-cyanocinnamates 15 in the presence of piperidine in refluxing MeCN yielded benzo[a]quinolizin-4-ones 16 (Scheme 4). Under the same conditions, 12 and arylidene malononitriles 19 reacted to give benzo[a]quinolizin-4-imines 20 (Scheme 5). Instead of 15 and 19, mixtures of an aromatic aldehyde, and ethyl cyanoacetate or malononitrile, respectively, can be used in a one-pot reaction. Introduction. ± Within the class of fused isoquinolines with their cardiovascular [1], anti-inflammatory [2], and antidepressant [3] activities, [1,2,4]triazolo[3,4-a]isoquinolines are of considerable pharmaceutical and agricultural interest [4 ± 7]. Therefore, the synthesis of this ring system is an attractive goal. A convenient approach is the 1,3-dipolar cycloaddition of nitrilimines [8 ± 10], generated by elimination of HX from corresponding hydrazonoyl halides [11 ± 13], to the CN bond of 3,4-dihydroisoquinolines [12] [14]. It has been shown that derivatives of type 1 can be obtained in high yields with R 1 H or alkyl [5] [6] [15] [16]. On the other hand, 3,4-dihydroisoquinolin-1-acetonitriles and hydrazonoyl halides in refluxing THF in the presence of Et 3 N reacted to give pyrrolo[2,1-a]isoquinoline derivatives of type 2 via a cyclocondensation reaction [15] [17]. Spirocyclic adducts of type 3, which could have been formed by 1,3-dipolar cycloaddition with the enamine tautomer of 3,4-dihydroisoquinolin-1-acetamide, have never been observed [6] [15] [17] 3 ).The recently reported results of the reaction of hydrazonoyl halides with 3,4-dihydroisoquinolin-1-acetamide 4 in the presence of Et 3 N [17] are in pronounced contrast to those published earlier [6]. Whereas the reaction of 5 in refluxing THF yielded only the cyclocondensation product 6, the structure of the product obtained from the reaction in CH 2 Cl 2 at room temperature was described as the cycloadduct 1a

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Chemistry of C-Heteroarylhydrazidoyl Halides. Synthesis and Reactions of N-(p-Nitrophenyl)-C-(2-thienyl)-formohydrazidoyl Halides

Cited by 60 publications

References 0 publications

Ethyl 7-Methyl-1-(4-nitrophenyl)-5-phenyl-3-(thiophen-2-yl)-1,5-dihydro-[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylate

Ethyl 7-Methyl-1-(4-nitrophenyl)-5-phenyl-3-(thiophen-2-yl)-1,5-dihydro-[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylate

Regioselective synthesis of some functionalized 3,4’-bis-(pyrazolyl)ketones and chemoselectivity in their reaction with hydrazine hydrate

New Routes to Fused Isoquinolines

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