Synthesis and Rearrangement of Ethyl Aryloxyglyoxalate Arylhydrazones

Shawali, Ahmad S.; Eweiss, N. F.; Hassaneen, Hamdi M.; Sami, M.

doi:10.1246/bcsj.48.365

Cited by 42 publications

(31 citation statements)

References 5 publications

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“…Treatment of 4 with hydrazonoyl chlorides 5a-c [5][6][7] in chloroform in the presence of triethylamine SCHEME 1 yields products that can be formulated as 12a-c or their isomeric structures 13a-c (Scheme 2). The reaction pathway that seems reasonable to account for the formation of 12 or 13 is outlined in Scheme 2.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Polyfunctional fused heterocyclic compounds via indene‐1,3‐diones

Abdallah

Abdelhadi

Hassaneen

et al. 2003

Heteroatom Chemistry

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Section: Resultsmentioning

confidence: 99%

“…Microanalyses were performed on a Perkin-Elmer 2400 CHN Elemental Analyzer at the microanalytical center, University of Cairo. Compounds 1a [3], 1b [1], 2 [4], 5a-c [5][6][7], 14 [8], 15 [9], 20a [10], 20b [10], and 20e [10] were prepared as previously described.…”

Section: Methodsmentioning

confidence: 99%

Polyfunctional fused heterocyclic compounds via indene‐1,3‐diones

Abdallah

Abdelhadi

Hassaneen

et al. 2003

Heteroatom Chemistry

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“…Elemental analyses were carried out at the Micro analytical Center of Cairo University. 6,7-dimethoxy-3,4-dihydroisoqinoline-1-acetonitrile 1 (Osbond, 1951) and the hydrazonoyl halides 13a (Eweiss & Osman, 1980), 13b (Shawali & Abdelhamid, 1976) and 15 (Shawali et al 1975) were prepared as previously described.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of New Derivatives of Heterocyclic Compounds Containing Pyridine, Pyrimidine and Triazole Ortho-Fused to Isoquinoline Moiety

Abunada¹,

Hassaneen²,

Miqdad³

2012

IJC

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Abstract4-Amino-9,10-dimethoxy-2-phenyl-6,7-dihydro-2(H)-pyrido[2,1-a]isoquinoline-1,3-dicarbonitrile derivatives 4a-c were obtained from the reaction of 6,7-dimethoxy-3,4-dihydroisoqinoline-1-acetonitrile 1 with arylidenemalononitrile 2a-c in boiling acetonitile in the presence of piperidine. The reaction of 4a-c with triethyl orthoformate in acetic anhydride at reflux give the ethoxymethyleneamino derivatives 5a-c. Compounds 5a-c were reacted with hydrazine hydrate and give the corresponding 4-amino-3-imino-2-aryl-3,4,8,9-tetrahydro-2(H)-pyrimido[5′,4′:5,6] pyrido [2,1-a]isoquinoline-1-carbonitrile derivatives 6a-c. Refluxing compound 6a in an excess of triethyl orthoformate give 7a. When compounds 6a-c were refluxed with acetic anhydride or benzoyl chloride in pyridine, they afford the corresponding 4-methyl and 4-phenyl derivatives 8a-c and 9a-c, respectively. Compound 6a was refluxed in diethyloxalate and give product 10. Also, the reaction of 6a with C-acylhydrazonoyl halides 13a,b in refluxing chloroform in the presence of triethylamine afford 14a,b. Correct elemental analyses and spectral data (IR, 1 H NMR, 13 C NMR and MS) confirm the structure of the synthesized compounds.

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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%